Rowansci sample output

1

All four direct radical jobs are now finished or materially resolved.

Results:

  • TEMPOL direct spin 8dde1157-d968-4e12-8686-428539e17f02: COMPLETED_OK
    • doublet energy: -598.100733 Ha
    • quartet energy: -597.927273 Ha
    • doublet favored by 0.173460 Ha, about 108.9 kcal/mol
  • TEMPOL direct redox 4e704c4f-93e8-4f2c-a493-ddccf283a0da: COMPLETED_OK
    • oxidation potential: 0.7835 V
    • reduction potential: -2.2366 V
  • Dopa semiquinone direct spin 364a9d1a-913f-4cb6-8bbf-a11a70d250ec: COMPLETED_OK
    • doublet energy: -515.919126 Ha
    • quartet energy: -515.799169 Ha
    • doublet favored by 0.119957 Ha, about 75.3 kcal/mol
  • Dopa semiquinone direct redox f61fe3a8-4805-44a0-a100-1f6411ff195b: COMPLETED_OK
    • oxidation potential: 1.5135 V
    • reduction potential: -0.3265 V

What this means:

  • The workaround is real. Rowan does support these radicals when passed as explicit molecule dicts with multiplicity=2.
  • The earlier failures were integration-path failures, not a fundamental backend inability to handle radicals.
  • Both radicals strongly prefer the doublet, which is chemically sensible and supports trusting this submission route.
  • On the redox side, dopamine semiquinone is much easier to reduce than TEMPOL and much harder to oxidize than TEMPOL in this setup. TEMPOL sits in a milder redox window than the semiquinone.

My chemistry read, with caution that these redox numbers were run in acetonitrile rather than cytosolic water:

  • This does not support TEMPOL as a direct covalent trap for dopamine o-quinone or aminochrome.
  • It does support TEMPOL behaving more like a redox-active radical mediator than a quinone adduct former.
  • The semiquinone stage remains the more plausible place for TEMPOL interaction than the closed-shell quinone stage.
2 
**Chemistry Memo**

Using only the completed direct-radical Rowan jobs, TEMPOL and dopamine semiquinone both behave as well-defined doublet radicals, but they occupy different redox regimes.

The spin-state results are internally consistent. TEMPOL strongly favors the doublet over the quartet by 0.173460 Ha (-598.100733 Ha vs -597.927273 Ha), which is about 108.9 kcal/mol. Dopamine semiquinone also strongly favors the doublet by 0.119957 Ha (-515.919126 Ha vs -515.799169 Ha), about 75.3 kcal/mol. So for both species, the open-shell doublet description is chemically stable and much more plausible than a higher-spin alternative in this setup.

The redox numbers separate the two radicals more clearly. TEMPOL gave an oxidation potential of 0.7835 V and a reduction potential of -2.2366 V. Dopamine semiquinone gave an oxidation potential of 1.5135 V and a reduction potential of -0.3265 V. Relative to TEMPOL, dopamine semiquinone is much harder to oxidize further and much easier to reduce. That places semiquinone in a more reduction-accessible window, while TEMPOL sits in a milder, more buffered nitroxide-like redox range.

The narrow conclusion supported by these completed numbers is that TEMPOL looks more like a redox mediator than a direct covalent trap for dopamine oxidation products. Dopamine semiquinone appears to be the more redox-labile species, while TEMPOL appears to be the more controlled persistent radical. On that basis, the more plausible interaction is TEMPOL participating in radical redox handling around the semiquinone stage rather than directly trapping quinone products such as aminochrome or dopamine o-quinone.

Completed workflows used for this memo:

* TEMPOL direct spin 8dde1157-d968-4e12-8686-428539e17f02
* TEMPOL direct redox 4e704c4f-93e8-4f2c-a493-ddccf283a0da
* Dopa semiquinone direct spin 364a9d1a-913f-4cb6-8bbf-a11a70d250ec
* Dopa semiquinone direct redox f61fe3a8-4805-44a0-a100-1f6411ff195b

One caution: these are comparative computational results from the completed Rowan runs, not direct cytosolic rate constants or proof of a specific reaction pathway.
3

I ran a minimal comparator on April 7, 2026 using oleanolic acid as the oxidized triterpenoid proxy and 4-hydroxy-2-nonenal (4-HNE) as the oxidized lipid electrophile proxy.

The result supports your idea. 4-HNE looks much more continuation-prone for Michael/adduct chemistry than oleanolic acid. In the dedicated Fukui runs, the global electrophilicity index was 1.4587 for 4-HNE versus 0.8503 for oleanolic acid, and the strongest positive Fukui terms were much higher for 4-HNE (about 0.20 vs about 0.105). Structurally that makes sense: 4-HNE contains an explicit alpha,beta-unsaturated aldehyde, which is a classic mobile Michael acceptor. Oleanolic acid does not; it is a rigid pentacyclic scaffold with a terminal carboxylic acid and no diffusible oxoaldehyde/enal motif.

The descriptor side points the same way. Oleanolic acid came back as a monocarboxylic acid (nAcid = 1), very rigid (nRot = 1), and bulky (MW 456.36). 4-HNE is smaller (MW 156.12), much more flexible (nRot = 6), and has no acid/base flag in the descriptor output. So the triterpenoid is biased toward being a relatively locked, termination-like oxidized product, while the lipid aldehyde is biased toward staying chemically propagative and protein-reactive.

So the short answer is: oxidized triterpenoids are often less likely to keep feeding chain/Michael chemistry because they oxidize into sterically shielded, rigid alcohol/ketone/carboxylate states, whereas oxidized lipids like 4-HNE form small, diffusible enal/oxoaldehyde electrophiles that are built to keep reacting. This is not universal, though: triterpenoids with real enone/quinone-methide motifs can still be quite electrophilic.

Workflows:

  • Oleanolic acid descriptors: 2fc326a4-b421-4a2c-b4b2-5ee3f07568c3
  • Oleanolic acid Fukui: 9cb860c8-557f-4dd6-8392-f6bdcd9f7166
  • Oleanolic acid pKa: 9b57b128-6eda-40b4-80f4-3f7293fa7cff still running
  • 4-HNE descriptors: 082046c5-03d5-40f5-93fc-2f13bd613207
  • 4-HNE Fukui: 92803e49-8a03-4095-8084-fcda001916b4
  • 4-HNE pKa: 20d25bab-481b-4ed3-9b49-8111569b5a56

If you want, I can do the cleaner oxysterol-specific follow-up next: oleanolic acid vs 7-ketocholesterol, or vs a cholesterol secosterol if you want the aldehyde-forming cholesterol side rather than the generic lipid side.

4

I ran the oxysterol-specific follow-up with 7-ketocholesterol against oleanolic acid.

7-ketocholesterol resolved and validated cleanly as a distinct oxidized cholesterol comparator. The important mechanistic difference versus the triterpenoid is already clear from the structure: 7-ketocholesterol contains a ring-confined enone/ketone motif, while oleanolic acid is a bulkier pentacyclic acid/alcohol scaffold with no small mobile oxoaldehyde-like handle. So my expectation is:

  • 4-HNE should remain the strongest continuation/Michael-adduct case.
  • 7-ketocholesterol should be more continuation-prone than oleanolic acid, but less than 4-HNE.
  • oleanolic acid should still look more like a comparatively terminal oxidized product than a propagating electrophile.

The Rowan jobs are submitted but still mostly sitting in queue, so I don’t have the final numeric comparison yet.

Workflow IDs:

  • 7-ketocholesterol pKa: 1d3f42ff-c430-44dc-9d0b-75ba639b2207
  • 7-ketocholesterol descriptors: 3148ca6f-e087-423c-88b4-3f5d23065ed6
  • 7-ketocholesterol Fukui: 6bf1a0d6-faa5-4470-9db8-1bcdf5f4d18b
  • Oleanolic acid pKa repeat: 04458ece-cce0-4843-b362-7ce28a5f6ce2
  • Oleanolic acid descriptors repeat: ba4b83c6-7866-4f94-8cab-5d3c975f6846
  • Oleanolic acid Fukui repeat: 4073491c-7d54-4183-adeb-19c6922f3a61

If you want, I can check these again after they finish and give you a clean three-way ranking: 4-HNE vs 7-ketocholesterol vs oleanolic acid.

5

You’re looking at three things mashed together: a lab notebook, a software bug report, and a mechanistic detective story. The chemistry question underneath all of it is simple enough, because apparently the universe enjoys hiding simple questions under UUID confetti: when dopamine gets oxidized, does TEMPOL directly bond to the quinone as a trap, or does it mostly hang around and manage electron/radical chemistry nearby? The final answer in the log leans much more toward the second option.

First, the clutter. The long strings like 8f209c14-... are just Rowan job IDs. “Worked for 7m 54s” is the prior agent’s runtime. “1 file changed” and the Python filenames are bookkeeping about scripts used to launch jobs. They are useful for reproducibility, but they are not chemistry conclusions. The notes about Rowan MCP/backend bugs mean the software interface had trouble handling radicals, especially from SMILES input, so part of the workflow had to bypass that and specify charge and spin more explicitly. There was also a schema typo in the redox tool. Glorious, ordinary software. Aminochrome appears only as a suggested future target, not as a completed result in this log.

The first phase was about the isolated radical species. TEMPOL, dopamine semiquinone, and protonated dopamine semiquinone were each tested for spin state and redox behavior. “Semiquinone” here means the half-oxidized radical intermediate between dopamine and the fully oxidized quinone. “Protonated semiquinone” is that same radical with an extra proton attached. All of them strongly favored the doublet state over quartet, which is chemistry’s way of saying the normal one-unpaired-electron radical picture is the right one and the higher-spin alternative is not competitive. The energy preferences were big, tens to over a hundred kcal/mol, so that part is pretty solid. The protonated runs initially stopped, but once Rowan credits were refilled they completed, which means the earlier STOPPED status was almost certainly a quota/interruption problem, not evidence that the molecule itself was impossible.

Then comes the redox comparison, which is where the first real mechanistic story shows up. TEMPOL behaved like a stable, buffered, persistent nitroxide radical. Dopamine semiquinone, and especially the protonated semiquinone, behaved like the more redox-labile partners. In plainer English: TEMPOL looks more like a recyclable radical/redox helper, while the dopamine-derived species look more like the fragile, reactive things being handled. That is why the memo keeps saying TEMPOL looks like a redox mediator rather than a direct quinone trap. Another way to say it is that TEMPOL looks less like molecular flypaper and more like a traffic cop for the ugly electron-transfer part of dopamine oxidation. The log’s interim conclusion was that the semiquinone stage is the most plausible place where TEMPOL matters.

But to be fair to the opposite hypothesis, the workflow then tried to force-test direct covalent trapping anyway. That is what the Fukui, TS, IRC, and scan jobs were about. The logic was: isolated-species redox data can suggest a mechanism, but they do not prove whether TEMPOL can or cannot actually cross a barrier and form a bond to dopamine o-quinone. So the software first ranked likely attack sites on dopamine o-quinone using a Fukui index calculation, which identified two quinone carbons, C11 and C10, as the top candidates. Then it tried transition-state searches for TEMPOL addition at those sites. Rowan’s default engine crashed on the open-shell jobs with a backend error, so those failures are not chemistry evidence. The fallback xTB workflow was then used instead.

For C11, the story never got to a clean validation. A distance scan showed a shallow minimum around 2.35 Å, and pushing TEMPOL closer became uphill. That means the system seems comfortable in a loose approach complex, but not eager to collapse into a bond. TS candidates could be generated, but the IRC kept failing with “more than one imaginary mode,” which means the structure was not a proper clean first-order transition state. So C11 stayed in the “plausible idea, not validated mechanism” bucket.

For C10, the plot briefly looked more exciting. A scan, then TS search, then IRC all returned COMPLETED_OK, and the mid-log interpretation said this might be the first fully validated direct TEMPOL addition route. But then came the actually important part: someone checked the geometries instead of worshipping the green status labels. The supposed forming TEMPOL O to quinone C10 distance was about 3.09 Å in the TS and in both IRC endpoints. That is not a covalent bond. The compressed “product guess” had been 1.90 Å, but the pathway relaxed away from that and stayed nonbonded. The closest contact was actually to a hydrogen, not the quinone carbon. So the later memo correctly walks back the earlier optimism: the C10 path validated an encounter complex / pre-reactive arrangement, not a real O-C bond-forming addition product.

So the final scientific takeaway is this: the log does not provide a validated direct covalent TEMPOL-addition mechanism to dopamine o-quinone. What it does support is a weaker, nonbonded, redox-proximal interaction. In other words, TEMPOL can approach and interact with the oxidized dopamine system, but these calculations did not show it actually snapping on as a stable quinone-trapping adduct. That keeps the best-supported picture as “TEMPOL helps manage radical/redox chemistry near semiquinone or related encounter states,” not “TEMPOL directly captures dopamine quinone by straightforward O-addition.” The suggestion at the very end follows from that: stop forcing only O-addition, and instead test hydrogen-transfer or electron-transfer-coupled encounter pathways.

Tiny jargon decoder, since chemistry likes to cosplay as a locked filing cabinet: a radical is a species with an unpaired electron; open-shell means the same basic thing. A doublet is the ordinary one-unpaired-electron radical state. A quartet is a higher-spin alternative. Redox potentials tell you how easily something gains or loses electrons. A transition state (TS) is the top of the barrier for one elementary reaction step. An IRC checks whether that TS really connects the intended starting structure to the intended product. A Fukui index is a reactivity map for likely attack sites. A scan is a calculation where you force one bond distance shorter or longer and watch the energy respond. xTB is a cheaper, lower-level computational method, useful for screening but not the last word on truth.

So the cleanest one-line summary is: the early isolated-molecule calculations supported TEMPOL as a redox mediator, and the later mechanistic tests failed to turn direct covalent trapping into a real validated pathway. The last memo in the file is the one to trust.

6

Worked for 1m

I checked the finished runs on April 7, 2026. The oxysterol follow-up came back consistent with the earlier hypothesis: 4-HNE > 7-ketocholesterol > oleanolic acid for continuation-prone electrophilic behavior.

From the dedicated Fukui runs, the global electrophilicity indices were:

  • 4-HNE: 1.4587
  • 7-ketocholesterol: 1.4283
  • oleanolic acid: 0.8586

The pKa contrast also helps. Oleanolic acid showed a strongest acid at about 4.30, so in aqueous/physiologic settings it is pushed toward a carboxylate form. 7-ketocholesterol showed no obvious ionization event in the tested pH 2-12 window, so it stays more neutral. Combined with the structural difference, that supports the mechanistic readout: 7-ketocholesterol has a real sterol enone/ketone electrophile and is more Michael-capable than the oxidized triterpenoid, while oleanolic acid is a bulky, rigid pentacyclic acid with much lower electrophilicity and no small mobile oxoaldehyde/enal handle.

So the clean takeaway is: oxidized triterpenoids like oleanolic acid look less likely to keep feeding chain/Michael chemistry than oxidized cholesterol products like 7-ketocholesterol, and both are still generally less continuation-prone than small lipid aldehydes like 4-HNE. If you want, I can turn this into a short table or a tighter mechanistic paragraph for notes/manuscript use.

ok yes turn it into that

Short Table

Comparator Key reactive motif Ionization in this test Global electrophilicity index Expected tendency to continue Michael/adduct chemistry
4-HNE Small alpha,beta-unsaturated aldehyde Not acid-like in this screen 1.4587 Highest
7-ketocholesterol Sterol enone/ketone No clear ionization event from pH 2-12 1.4283 Intermediate
Oleanolic acid Rigid pentacyclic carboxylic acid, no mobile enal/oxoaldehyde pKa ~4.30 0.8586 Lowest

Mechanistic Paragraph

A small test run on April 7, 2026 supports the idea that oxidized triterpenoids are less likely than oxidized cholesterol or lipid products to keep propagating free-radical or Michael-type adduct chemistry. In this comparison, 4-HNE showed the strongest electrophilic profile, 7-ketocholesterol was intermediate, and oleanolic acid was clearly lower (1.4587 > 1.4283 > 0.8586 by global electrophilicity index). Mechanistically, this fits the structures: 4-HNE is a small, diffusible alpha,beta-unsaturated aldehyde, and 7-ketocholesterol retains a bona fide sterol enone/ketone electrophile, whereas oleanolic acid is a bulky, rigid pentacyclic scaffold that lacks a mobile oxoaldehyde/enal handle and is additionally biased toward a carboxylate state (pKa ~4.30). That combination makes the oxidized triterpenoid look more like a comparatively terminal or damped oxidation product, while oxidized lipids and some oxysterols remain better configured to continue electrophilic chain chemistry and covalent adduct formation.

If you want, I can also rewrite this into a more formal manuscript-style sentence pair or a figure legend.

Why are oxidized retinoids less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins? No answer yet · Last followed 1y Why are oxidized xanthophyll carotenoids (like lutein) less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins? No answer yet · Last followed 1y

I’m checking a few primary/review sources to keep the chemistry claims tight. Then I’ll turn both questions into a single mechanistic answer with the key differences from oxidized lipids and proteins.

USE ROWANSCi to answer this: “Why are oxidized retinoids less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins? No answer yet · Last followed 1y Why are oxidized xanthophyll carotenoids (like lutein) less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins? No answer yet · Last followed 1y”

Worked for 3m 2s

Using Rowan as a quick proxy panel, the two questions do not come out the same.

For oxidized retinoids, Rowan does not support a blanket “less reactive than lipid aldehydes” claim. Using all-trans retinoic acid as the oxidized-retinoid proxy, Rowan gave a global_electrophilicity_index = 2.2685, which is actually higher than the lipid-electrophile controls I ran in parallel: 4-HNE = 1.4785 and acrolein = 1.6281. So the careful answer is: oxidized retinoids are not automatically less able to engage electrophilic chemistry. What is often different is the mode of reactivity. Retinoids tend to keep a large, conjugated, bulky scaffold, and their electrophilicity is spread across a long polyene rather than concentrated into a tiny mobile alpha,beta-unsaturated aldehyde like 4-HNE or acrolein. That usually means less “small diffusible chain-propagator” behavior, but not necessarily less intrinsic electrophilicity. In other words, for retinoids the limitation is often accessibility, partitioning, sequestration, and oxidation pathway, not a universally weak Michael-acceptor profile.

For xanthophyll carotenoids like lutein, the user’s intuition is more defensible. Rowan validated lutein cleanly as a very large oxygenated polyene (MW 568.89) with two oxygens and no compact aldehyde/enal handle. That matters because the intact xanthophyll scaffold is usually too large and too delocalized to behave like the classic lipid-derived chain electrophiles. Lipid peroxidation gives small, highly mobile, carbonyl-focused species such as 4-HNE and acrolein; intact xanthophylls are more likely to quench radicals or undergo local oxidation, epoxidation, or cleavage than to act as roaming oxoaldehyde/Michael-adduct agents. The important caveat is that if a carotenoid is cleaved into smaller apocarotenals, those fragments can become electrophilic exceptions.

So the short version is:

  • Oxidized retinoids: not safely generalizable as “less electrophilic”; Rowan’s retinoic-acid proxy was actually quite electrophilic.
  • Intact oxidized xanthophylls: more plausibly less chain-propagative than oxidized lipids, because they usually lack the small, focused enal/oxoaldehyde motif that makes lipid aldehydes so adduct-prone.
  • Oxidized proteins: are not really the best comparison class for chain propagation, because proteins are usually the local adduct targets or carbonylated endpoints, not the small mobile electrophiles that keep the chain moving.

Rowan runs used here:

  • Retinoic acid descriptors: 20927e66-60df-4c48-b662-cbb9ad99645e
  • Retinoic acid Fukui: c2f6d294-13fb-4545-ad9d-b3b1057e6298
  • 4-HNE descriptors: 4c14e144-73b0-4099-a760-4a9e558f3e0f
  • Acrolein descriptors: 9d862c36-56fa-4846-a74a-16267f36ffbb
  • Lutein descriptors: ab4be108-3413-4a0e-bec9-a2a77fc1b371 still running

If you want, I can turn this into two polished Q&A-style answers, one for retinoids and one for xanthophylls, with the caveats already baked in.

and try zeaxanthin next too

Worked for 28s

Zeaxanthin is now in the Rowan panel.

It validated cleanly as C40H56O2 with MW 568.89, essentially the same gross formula/class as lutein, so the prior xanthophyll interpretation should carry over at least qualitatively: intact zeaxanthin is a large oxygenated polyene, not a compact lipid-style enal/oxoaldehyde electrophile. That makes it more plausible as a radical sink or local oxidation substrate than as a small mobile chain-propagating Michael acceptor. That last sentence is still an inference until the Rowan property jobs finish.

Current workflow status:

  • Zeaxanthin descriptors: f479ba2f-2605-41b2-ba4a-a8c62101037a
  • Zeaxanthin Fukui: 9268f8e1-ed7e-4467-96ee-280f4e4e031b
  • Lutein descriptors: ab4be108-3413-4a0e-bec9-a2a77fc1b371 still running
  • Lutein Fukui: 89addb12-1c35-49f7-9e5e-3f5bdee63aa5 still queued

The retinoid result remains the main caution: retinoic acid did not behave like a weak electrophile in Rowan, so I would not group oxidized retinoids and xanthophylls together as one “less reactive than lipids” bucket without qualification. When the zeaxanthin and lutein jobs finish, I can give you a cleaner split:

  • retinoids: structurally bulky, but not necessarily weakly electrophilic
  • xanthophylls: more likely to stay in the “large delocalized antioxidant/polyene” regime unless cleaved into smaller apocarbonyls

“can turn this into two polished Q&A-style answers” yes do that next

Q1
Why are oxidized retinoids less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins?

A
They are not necessarily less likely in any blanket chemical sense. The better distinction is that oxidized retinoids often react differently from oxidized lipids, not that they are always weaker electrophiles. In a quick Rowan panel run on April 7, 2026, all-trans retinoic acid did not look intrinsically mild: its global electrophilicity index came back at 2.2685, which was actually higher than the lipid aldehyde controls 4-HNE (1.4785) and acrolein (1.6281). That means you should be cautious about saying oxidized retinoids are simply “less reactive.”

What usually differs is the form of the reactivity. Lipid peroxidation tends to generate small, mobile, carbonyl-focused electrophiles such as 4-HNE, acrolein, and related oxoaldehydes. Those are efficient chain propagators and protein adduct formers because the electrophilic center is compact, exposed, and diffusible. Oxidized retinoids, by contrast, often remain attached to a long, bulky, highly conjugated scaffold. Their electron deficiency can be spread across a larger polyene system rather than concentrated into a tiny roaming alpha,beta-unsaturated aldehyde. So even when an oxidized retinoid is electrophilic, it may be less effective as a freely diffusing chain-propagating oxoaldehyde than a lipid-derived aldehyde. In short: for retinoids, the limitation is often accessibility, localization, and oxidation pathway, not universally low electrophilicity.

Q2
Why are oxidized xanthophyll carotenoids like lutein or zeaxanthin less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins?

A
This claim is more defensible for intact xanthophylls than for retinoids. Lutein and zeaxanthin are very large oxygenated polyenes, not compact carbonyl electrophiles. Rowan validated zeaxanthin as C40H56O2 with MW 568.89, and lutein resolves to the same gross class. Structurally, these molecules have long delocalized conjugated systems and terminal hydroxylated ring motifs, but they do not start out as small enal/oxoaldehyde species of the kind that drive lipid-derived Michael chemistry. That makes intact xanthophylls much less well configured to behave like classic roaming chain-propagating electrophiles.

By contrast, oxidized lipids readily fragment into small aldehydes and enals such as 4-HNE and acrolein, which are exactly the kinds of molecules that diffuse, attack nucleophilic protein residues, and keep electrophilic damage moving through the system. Proteins are also usually the adduct targets or terminally carbonylated products, not the main source of small mobile chain electrophiles. So the practical answer is that intact oxidized xanthophylls are more likely to remain bulky, localized, and delocalized, whereas oxidized lipids are more likely to produce small focused carbonyl fragments that continue chain reactions and Michael addition chemistry. The main caveat is cleavage: once a carotenoid breaks into smaller apocarotenals or related fragments, those products can become much more electrophilic and start to resemble the lipid-derived exceptions.

If you want, I can also rewrite these into a more forum-style version with slightly shorter sentences and no Rowan jargon.

7

Here are cleaner forum-style versions.

Q1
Why are oxidized retinoids less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins?

A
They are not always less likely. The safer answer is that oxidized retinoids often behave differently from oxidized lipids, rather than simply being weaker electrophiles.

Oxidized lipids often break down into small, mobile aldehydes and enals such as 4-HNE or acrolein. Those are very good at continuing damage because they are small, diffusible, and have a concentrated electrophilic center that readily reacts with nucleophilic amino acids through Michael addition or carbonyl chemistry.

Oxidized retinoids usually stay attached to a much larger conjugated scaffold. Even when they become electrophilic, that reactivity is often spread across a long polyene system rather than concentrated into a tiny roaming alpha,beta-unsaturated aldehyde. So they may be less effective as freely diffusing chain-propagating oxoaldehydes, even if they are still chemically reactive.

So the short version is: oxidized lipids are especially dangerous because they often generate small mobile electrophiles, while oxidized retinoids more often remain large, delocalized molecules whose reactivity is less focused and less diffusible. The caveat is that you should not assume all oxidized retinoids are weak electrophiles, because some can still be quite reactive.

Q2
Why are oxidized xanthophyll carotenoids like lutein or zeaxanthin less likely to form free radical/oxoaldehyde chain reactions or Michael adducts than oxidized lipids/proteins?

A
This is easier to defend for intact xanthophylls. Lutein and zeaxanthin are large oxygenated carotenoids with long conjugated chains, not small carbonyl electrophiles.

Lipid peroxidation tends to produce small aldehydes and enals that can diffuse away, keep the chain reaction going, and form Michael adducts with proteins. Intact oxidized xanthophylls are usually too large and too delocalized to do that efficiently. They are more likely to quench radicals, undergo local oxidation, or remain membrane-associated than to act like classic roaming lipid-derived electrophiles.

That is why oxidized lipids are much more associated with chain-propagating oxoaldehyde chemistry, while intact oxidized xanthophylls are less likely to behave that way. The main exception is if the carotenoid is actually cleaved into smaller apocarotenal fragments. Once that happens, the fragments can become much more electrophilic and start to resemble lipid-derived aldehydes.

If you want, I can make these even shorter and more conversational, like a direct post reply.

8

I queued the next Rowan panel, but Rowan is currently backed up and none of these new jobs have started yet, so I do not have final computed indices for them in this turn.

Queued now:

  • Curcumin descriptors: b55f4deb-3fd9-4c08-8c73-f20799d910de
  • Curcumin Fukui: 54189197-59cd-4fc2-b656-717caea81a61
  • p-Benzoquinone descriptors: 6569341e-4632-40af-8d2a-116294b1756f
  • p-Benzoquinone Fukui: b5bc0473-ace5-4069-9bcd-e2e7cd8776c1
  • Allicin descriptors: f40de8f7-9140-402d-bf83-c5cec323ee6c
  • Allicin Fukui: acb7c3a2-a044-47ed-9498-2dcfc57c39f4
  • 6-Shogaol descriptors: ff547cef-a1e9-4a5b-9b7f-dcefb1a03520
  • 6-Shogaol Fukui: 02178f7d-d1ef-4308-becd-207dbd822e6d
  • Zeaxanthin descriptors: f479ba2f-2605-41b2-ba4a-a8c62101037a
  • Zeaxanthin Fukui: 9268f8e1-ed7e-4467-96ee-280f4e4e031b

Even before the numbers come back, the chemistry points in a fairly clear direction. These are not all in the same bucket:

  • p-Benzoquinone is a compact quinone Michael acceptor, so it is likely to be strongly adduct-prone.
  • 6-Shogaol has a classic alpha,beta-unsaturated ketone, so it is also likely to be strongly Michael-reactive.
  • Curcumin has conjugated enone/dicarbonyl character, so it is plausibly electrophilic, though its larger delocalized scaffold may make it less “small mobile aldehyde-like” than 4-HNE.
  • Allicin is reactive too, but in a different way. It is mainly a sulfur electrophile and thiol-transfer oxidant rather than a classic lipid-style Michael acceptor.
  • Zeaxanthin, like lutein, is still the intact-xanthophyll case: large, delocalized, membrane-associated, and less obviously set up as a roaming oxoaldehyde/Michael electrophile unless it cleaves into smaller fragments.

So the provisional answer is that oxidized quinones and shogaol-like products are probably much closer to lipid-electrophile behavior than intact xanthophylls are, while allicin is reactive by a different sulfur-centered mechanism. If you want, I can check the Rowan queue again after these finish and turn it into a ranked table against 4-HNE and acrolein.

9

Yes. The extra data change the reading a lot. The sheet is not giving you one simple “badness” axis. It’s giving you at least two: generic chemical/electronic reactivity from DescGEI and FukuiGEI, and context-aware adduct propensity from adduct_call plus motif. That is why zeaxanthin and lutein come out extremely high on the raw scores yet still get Low direct, while sulforaphane has only middling raw scores but gets High via NCS, and dopamine and norepinephrine sit around 0.8 on the raw scores yet still get High after oxidation. Chemistry, as usual, refuses to fit into a neat spreadsheet morality scale.

What I find most surprising:

  • Cyanidin is a total outlier. It scores 7.6454 / 6.8166, which is way above even p-benzoquinone at 2.9846 / 2.9566 and o-benzoquinone at 2.9265 / 2.8929. That means the model is treating anthocyanin oxidation space as extremely hot, not just mildly quinone-like. That is interesting enough that I would not blindly trust it without later adduct benchmarking, because it is not just “high,” it is in a different league.

  • Oxidation-state flips are one of the clearest signals in the whole panel. alpha-Tocopherol is 0.8231 / 0.7886 and Low, but alpha-tocopheryl quinone jumps to 2.7604 and Moderate-high. Cholesterol is 0.7078 / 0.6665 and Low, while 7-ketocholesterol is Moderate-high with FukuiGEI 1.4283. That is a strong repeated message: the parent scaffold is often not the real issue, the oxidized descendant is.

  • Small motif changes matter more than “natural product” branding. 6-Gingerol is 1.2653 / 1.0922 and Moderate direct, while 6-shogaol is High and explicitly tagged as an alpha,beta-unsaturated ketone. Same botanical neighborhood, very different electrophile logic. That is exactly the kind of shift you’d expect when a softer ketol becomes an enone warhead.

  • Phenolic/catechol identity matters more than size or steroid-ness. Estradiol is 1.6687 / 0.8323 with Moderate-high after oxidation, while testosterone is 1.1186 / 0.8674 with Low-moderate direct. Likewise dopamine and norepinephrine do not look terrifying on the raw GEIs, but the file still flags them as dangerous after oxidation. So the sheet is strongly implying that oxidizable phenolic/catechol chemistry matters more than the gross scaffold family.

  • Bulky polyenes and bulky tea products are teaching two different lessons. Zeaxanthin and lutein are the weirdest case: very high raw GEIs, still Low direct, which says raw electronic softness or delocalization is not enough for direct adduct danger. By contrast, theaflavin (2.5523 / 2.0905), theasinensin A (2.0051 / 1.8405), and oolonghomobisflavan B (1.7163 / 1.8924) stay fairly high but are annotated as moderate after further oxidation and/or bulky. So bulk does not erase reactivity, but it clearly modulates how directly the reactivity can express itself.

  • Protective molecules are not chemically inert. Glutathione is 1.328 / 1.1971 even though it is called a redox buffer thiol trap. Melatonin and AFMK are both around 1.0 and still sit in the low or low-moderate zone. That tells you the GEI-like scores are measuring “chemical engagement” more than simple hazard. A trap can be reactive because that is literally its job. Humans do love calling everything reactive “bad,” which is not how scavengers work.

The most important methodological surprise in the new file is that the panel design got smarter. You did not just add more suspicious plant molecules. You added whole missing motif families: sesquiterpene lactones like parthenolide and helenalin, withanolides like withaferin A, more isothiocyanates, a deeper naphthoquinone/catechol set, protective comparators like ascorbate, urate, ovothiol, carnosine, and plasmalogen representatives explicitly labeled Low direct; oxidation fragment risk. That means the next phase can actually distinguish direct warheads, oxidation-conditional liabilities, and true scavenger/trap chemistry instead of mushing them together. The fact that ascorbate is even represented with charge -1 shows the panel is starting to treat protective chemistry a little less like a children’s cartoon.

So the short interpretation is this:

The score columns are not damage scores. They look more like a measure of how electronically/reactively “live” a molecule is. The adduct_call and motif columns are doing the real biological interpretation, because they encode whether that reactivity is likely to stay diffuse, require oxidation first, or present as a direct cysteine/lysine-hitting warhead.

That brings us back to sulforaphane. The file actually supports your point in a sneaky way. It is the cleanest example here of a molecule that is not wildly high on the generic scores but is still singled out as High via NCS because its motif matters. The file cannot prove TF activation by itself, but it does support the idea that sulforaphane is a specialized signaling electrophile, not just “another random reactive compound.” In plain English: its usefulness probably comes from the same chemistry that makes it reactive at all.

My single biggest surprise is still cyanidin. My second biggest is zeaxanthin/lutein. Those three cases together basically tell you the panel is separating:

  1. things that are electronically hot,
  2. things that are direct adduct threats,
  3. things that become threats only after oxidation.

If you force one conclusion out of the file, it is this: “natural product” is a useless category here. Motif and oxidation state dominate.

10

5.4Pro

Yes. This update sharpens the picture a lot, but it sharpens it in a very annoying way: it makes “safe” split into low direct electrophile risk versus still chemically active in other ways. Those are not the same thing. This file updates the adduct / oxidation / electrophile map well. It does not by itself settle full biological safety, because dose, exposure, metabolism, localization, receptor pharmacology, and chronic use are mostly outside the table.

Here are the extra surprises I see.

1) The biggest mismatch is still raw score versus actual direct-risk call.
Zeaxanthin and lutein are among the highest raw scorers in the whole completed set, at 2.5428 / 2.8094 and 2.4511 / 2.6915, but they are still called Low direct. Meanwhile dopamine and norepinephrine sit down near 0.81 and 0.80 on the raw metrics, yet get High after oxidation. That means the sheet is really teaching a two-step lesson: raw GEI-like scores tell you a molecule is electronically “live,” but the motif + oxidation route decide whether that liveliness becomes a real adduct problem.

2) Oxidation-state flips are not a side note. They are one of the central laws of the panel.
alpha-Tocopherol is 0.8231 / 0.7886 and Low, but alpha-tocopheryl quinone jumps to 2.7604 and Moderate-high. Cholesterol is 0.7078 / 0.6665 and Low, while 7-ketocholesterol is Moderate-high with FukuiGEI 1.4283. That is not random. The file keeps saying: many parent lipids or antioxidants are not the main hazard, but their oxidized descendants can cross into a different chemical regime.

3) Some “protective” molecules are surprisingly reactive on paper.
Glutathione comes in at 1.328 / 1.1971 despite being labeled redox buffer thiol trap and Low direct. That is actually quite telling. It suggests the model is not measuring “toxicity” so much as capacity to engage chemically. A trap has to be reactive enough to trap things. So this file nudges me away from the childish idea that protective molecules are chemically boring. They are often busy on purpose.

4) The melatonin branch looks safer than I might have guessed.
Melatonin, AFMK, 6-hydroxymelatonin, and cyclic 3-hydroxymelatonin all cluster around roughly 1.0 raw score and stay in the Low direct to Low-moderate direct zone. That is interesting because it means “oxidized metabolite” does not automatically mean “more adduct-dangerous.” Compare that with catechols, where oxidation is basically the whole problem. So the sheet is not just rewarding oxidation in general. It is rewarding specific oxidation motifs.

5) Tiny structural edits are making very humanly inconvenient differences.
6-Gingerol is Moderate direct at 1.2653 / 1.0922, while 6-shogaol is explicitly High and tagged as an alpha,beta-unsaturated ketone. Same family, different warhead. Capsaicin versus dihydrocapsaicin shows a milder version of the same story: 1.0897 / 1.0270 falls to 0.9585 / 0.8962 when the scaffold is reduced, but both remain only Low-moderate direct. So unsaturation matters, but not every unsaturated natural product suddenly becomes acrolein’s evil cousin.

6) Lipid unsaturation is showing up where it should.
Cholesteryl linoleate edges above cholesteryl oleate on the Fukui side, 1.1429 versus 1.0083, even though both are still Low direct. The new plasmalogen rows make the same point even more explicitly by calling them Low direct; oxidation fragment risk. Translation: intact complex lipids may not be the direct electrophiles, but unsaturation and oxidation-fragment chemistry are quietly waiting in the wings. That is a subtle but important caution signal.

7) A few entries are more reactive than their reputations would lead people to assume.
Coumarin is sitting at 1.9120 / 1.8745 with Moderate-high. Retinoic acid is 2.2685 and Moderate-high. Erinacine A lands at 1.8941 / 1.8941 and Moderate-high. None of those are in the “instantly terrifying” bin, but they are definitely not reading as chemically sleepy. That is a useful correction to any instinct that “famous natural product” means “gentle.”

8) Cyanidin is still weird enough that I’d flag it as a watch item, not just accept it.
At 7.6454 / 6.8166, it remains absurdly above almost everything else. I believe the qualitative story, meaning anthocyanin oxidation can generate nasty quinone-like chemistry. But the magnitude is such an outlier that I would treat it as “important and likely real in direction, maybe exaggerated in scale until benchmarked.” That is one of the few rows I’d actively stress-test later.

So, does this update which compounds look safer and which deserve more caution?
Yes, for this specific chemical-risk frame.

What now looks safer for direct adduction, or at least less alarming in this panel:
glutathione, cysteine, homocysteine, ergothioneine, alpha-tocopherol, melatonin and its metabolites, cholesterol, ergosterol, beta-sitosterol, limonene, oleanolic acid, testosterone, lutein, zeaxanthin, cholesteryl oleate, cholesteryl linoleate. But I would say that carefully. For lutein/zeaxanthin the file says low direct, not “chemically irrelevant.” For cholesteryl esters and plasmalogens, the parent looks calmer than the oxidation products/fragments likely are.

What now looks more caution-worthy:
the obvious direct electrophiles like 4-HNE, acrolein, p-benzoquinone, o-benzoquinone, p-quinone methide, cinnamaldehyde, 6-shogaol, sulforaphane, allicin; the oxidation-conditional cluster like cyanidin, quercetin, fisetin, rosmarinic acid, naringenin, dopamine, norepinephrine, estradiol, theaflavin, theasinensin A, oolonghomobisflavan B; and the oxidation-shifted forms like 7-ketocholesterol and alpha-tocopheryl quinone. Retinoic acid, coumarin, erinacine A, curcumin, and bergamottin also deserve more respect than a casual “natural compound” label would suggest.

On sulforaphane, this update makes me more precise, not more alarmist. I would classify it as:
chemically caution-worthy, biologically often beneficial, mechanistically special.
It is still a direct electrophile, but not in the same style as acrolein. The file’s High via NCS call says the important thing is the isothiocyanate motif, not just a giant raw GEI number. So I’d be cautious with it as a reactive signaling compound, not dismiss it as dangerous in the same undifferentiated sense as hard damage electrophiles.

My bottom-line update would be this:

  • I’m less worried than raw scores alone would suggest about lutein, zeaxanthin, melatonin-family metabolites, and several intact sterol/lipid parents.
  • I’m more cautious than a supplement-friendly intuition would suggest about oxidation-prone catechols/polyphenols, quinone-adjacent compounds, oxidized lipid/antioxidant products, and motif-defined electrophiles like sulforaphane, 6-shogaol, and cinnamaldehyde.
  • The safest reading is not “reactive bad, antioxidant good.” It is parent scaffold + oxidation state + motif. Human labeling is lazy; the chemistry is not.

The cleanest practical distinction from this file is:
watch direct warheads, watch oxidation-prone phenolics/catechols under stress conditions, and do not confuse low direct adduct risk with total safety.

11

This upload is actually useful. The extra descriptors make the panel look less like a vibes spreadsheet and more like a three-gate model:

  1. Does it have a real warhead? Quinone, quinone methide, enone, isothiocyanate, alpha-methylene-gamma-lactone.
  2. Can it physically get at proteins? Small or moderately lipophilic compounds do better here than giant, donor-rich, polar bricks.
  3. Is it already armed, or does it need oxidation or metabolic activation first?

Once you read it that way, most of the weird rows stop being weird. Thymoquinone passes all 3 gates. Theaflavin passes gate 1 but is huge and polar. Dopamine needs oxidation first. Naphthalene is a famous toxicant but still looks low-direct here because its real problem is bioactivation, not native electrophilicity.

The new file actually strengthens the black tea point. Theaflavin is 564 Da with TopoPSA 217.6, 12 H-bond acceptors, 9 donors, and still only lands at Moderate after further oxidation. Theasinensin A and Oolonghomobisflavan B are even more ridiculous, around 914 to 928 Da with TopoPSA 394.74 and 16 donors each. So yes, they are electronically active, but they are also physically cumbersome. They do not look like small roaming quinones. That is one of the best examples in the sheet of “oxidized” not meaning “major direct adduct threat.”

The other very nice surprise is coffee metabolism. The metabolite panel looks much tamer than people’s reflexive “polyphenols must all become quinones” panic. Quinic acid is Low direct at 0.9997 / 0.8172, hippuric acid is Low direct despite 1.5221 / 1.4663, and trigonelline is especially funny: 1.9147 / 1.9147 but still Low direct because it is a zwitterionic alkaloid metabolite. Ferulic acid, isoferulic acid, protocatechuic acid, and dihydrocaffeic acid mostly sit in Moderate or Moderate after oxidation territory instead of screaming “direct warhead.” That looks a lot like metabolism often de-weapons the chemistry rather than sharpening it.

The cleanest oxidation switch in the whole new set is carnosic acid → carnosol. Carnosic acid is only 1.0104 / 1.2345 and called Moderate after oxidation, but carnosol jumps to 1.1528 / 2.9314 and gets High direct. That is a gorgeous little lesson: some “antioxidant” diterpenes are not just passive shields. They can flip into direct electrophile space after oxidation. It mirrors the older alpha-tocopherol → alpha-tocopheryl quinone story, but this one feels even sharper because both compounds live in the same rosemary/sage-type neighborhood people love to romanticize. Plants remain little chemistry gangs.

The new direct-electrophile families came in exactly as expected, which is good news if you enjoy being vindicated by lactones and quinones. Deoxyelephantopin is 2.1196 / 2.4419 and High direct. Alantolactone is lower on the raw numbers, 1.3286 / 1.4033, but still High direct, which tells you the motif class matters more than the absolute score alone. Celastrol comes in at 2.3403 / 2.4089 and High direct, while also being very lipophilic at SLogP 6.698, which is a rough “sticky electrophile” signature. Thymoquinone is Very high at 2.6866 / 2.7863, Shikonin is High direct at 2.9994 / 1.8722, and Embelin is High direct at 2.7744 / 1.4033. So the missing quinone / methide / sesquiterpene-lactone space did not mellow out once you added it. It got meaner.

A really important surprise is the PAH result, because it shows a limitation of the panel very clearly. Naphthalene and anthracene are both Low direct, even though humans do not generally list them under “probably fine, sprinkle generously.” That makes sense here: this panel is reading native direct electrophile/adduct risk, not CYP-generated epoxide danger. So it is probably undercalling compounds whose harm depends on metabolic activation rather than being born reactive. That is not a flaw so much as a warning label on how to read the map.

A few smaller surprises:

  • Xanthohumol at 1.808 / 1.7614 and Moderate-high is not sleepy at all. Hops are not automatically innocent.
  • CAPE at 1.8083 / 1.2163 is a bit softer than xanthohumol but still not a free pass.
  • Sucralose being Low direct tells you chlorination alone does not make something a covalent menace.
  • Oleic acid being Low direct; oxidation fragment risk fits the recurring theme that intact parent lipids can look calm while their breakdown products are the real troublemakers.

So yes, this does update the caution map.

I’m now less worried in this specific direct-adduct framework about:
black tea oligomers, coffee metabolites like quinic acid and hippuric acid, trigonelline, sterol parents, melatonin-family compounds, glutathione/cysteine/ergothioneine, oleic acid as the parent, lutein/zeaxanthin, and even boring things like sucralose as far as direct electrophile logic goes.

I’m more cautious with:
compact quinones and quinone methides like thymoquinone, embelin, celastrol, benzoquinones; sesquiterpene lactones like deoxyelephantopin and alantolactone; carnosol as an oxidation-switched diterpene phenol; and the usual motif-defined signaling/reactive compounds like sulforaphane, cinnamaldehyde, 6-shogaol, plus oxidation-prone phenolics when stressed into the wrong state. Xanthohumol and CAPE also move upward into the “respect this chemistry” bucket rather than the “food compound, therefore angelic” bucket.

But the caveat matters. “Safer here” means lower direct electrophile/adduct risk in this panel. It does not mean universally safe. Naphthalene is the perfect counterexample: low-direct here, still not something you’d market as wellness dust. And the reverse is also true: a direct electrophile can still be biologically useful if it is sensor-biased or dose-limited, which is the whole point of things like sulforaphane.

The biggest conceptual upgrade from this file is this: oxidation can do two opposite things. It can bulk up and tame a scaffold, like black-tea products, or it can arm and sharpen it, like carnosol, quinones, and oxidized lipids. That split is more informative than almost any “antioxidant vs toxin” label humans like to slap on molecules.

12 
class,compound,status,desc_workflow,fukui_workflow,DescGEI,FukuiGEI,molecular_formula,MW,nRot,nHBAcc,nHBDon,nAcid,nBase,SLogP,TopoPSA,MolVol,FlexIdx,charge,multiplicity,pKa_or_ionization,adduct_call,motif
lipid_controls,4-HNE,completed,4c14e144-73b0-4099-a760-4a9e558f3e0f,92803e49-8a03-4095-8084-fcda001916b4,1.4785,1.4587,,156.12,6,,,,,,,,,,,Very high,lipid alpha beta unsaturated aldehyde
lipid_controls,Acrolein,completed,9d862c36-56fa-4846-a74a-16267f36ffbb,,1.6281,,,,,,,,,,,,,,,Very high,small roaming enal
sterols,7-Ketocholesterol,completed,3148ca6f-e087-423c-88b4-3f5d23065ed6,6bf1a0d6-faa5-4470-9db8-1bcdf5f4d18b,,1.4283,,,,,,,,,,,,,no ionization pH 2-12,Moderate-high,oxidized sterol ketone
sterols,Ergosterol,completed,,,1.1528,,,,,,,,,,,,,,,,Low-moderate,parent fungal sterol
sterols,Cholesterol,completed,,,0.7078,0.6665,,,,,,,,,,,,,,,Low,parent sterol
sterols,Cholesteryl oleate,completed,2a110f59-c382-49e6-b44f-aac032ee147e,b017709f-b6e5-4af5-9a79-84fc489902f0,1.0372,1.0083,,650.6,21,2,0,0,0,13.977,26.3,710.216,0.893,,,,Low direct,intact cholesteryl ester
sterols,Cholesteryl linoleate,completed,09847d0d-13a5-4cb1-9015-1edda90c80f1,7ee3d13a-5be6-491b-ad12-3acb02b46869,0.9915,1.1429,,648.585,20,2,0,0,0,13.753,26.3,428.648,0.32,,,,Low direct,intact cholesteryl PUFA ester
sterols,beta-Sitosterol,completed,d096ac32-cca8-4d28-ace7-3eb09535e68f,c6d7320c-3c12-484e-8b00-701f373ef3a3,0.9767,0.872,,398.355,3,1,1,0,0,7.699,20.23,288.888,0.262,,,,Low-moderate,parent phytosterol
polyphenols,Cyanidin,completed,34e52ef8-4282-4b83-b953-def9d05197e7,af60c3c8-3570-4d18-9016-67d4fcb3fc17,7.6454,6.8166,,,,,,,,,,,,,,,High after oxidation,anthocyanin quinone concern
polyphenols,p-Benzoquinone,completed,6569341e-4632-40af-8d2a-116294b1756f,b5bc0473-ace5-4069-9bcd-e2e7cd8776c1,2.9846,2.9566,,,,,,,,,,,,,,,Very high,compact quinone Michael acceptor
polyphenols,o-Benzoquinone,completed,f2b254a0-1b28-49f2-9ba0-7c1759720c8b,6bb134e8-41f4-4082-b478-5a4681339caf,2.9265,2.8929,,,,,,,,,,,,,,,Very high,compact quinone Michael acceptor
polyphenols,p-Quinone methide,completed,7984e9c3-532c-434d-9ac3-bc521c12d2d3,3c5c0798-6fe4-4d42-9736-13170e2f8466,2.1574,,,,,,,,,,,,,,,,High,quinone methide
polyphenols,Curcumin,completed,b55f4deb-3fd9-4c08-8c73-f20799d910de,54189197-59cd-4fc2-b656-717caea81a61,2.1417,,,,,,,,,,,,,,,,Moderate-high,conjugated enone quinonoid scaffold
polyphenols,Quercetin,completed,ddd77c60-c634-49e7-8953-d048cef48d0b,712d2ea2-64f7-4bb1-b4be-795c99d62a37,1.7938,1.8724,,302.043,1,7,5,0,0,1.988,86.71,237.952,0.893,,,,Moderate-high after oxidation,flavonol catechol polyphenol
polyphenols,Coumarin,completed,6002f1b7-8757-4512-8d6d-18ad4591ae29,27b6e3e0-f151-4b52-aa2d-546143714849,1.912,1.8745,,146.037,0,2,0,0,0,1.793,30.21,128.04,0.326,,,,Moderate-high,benzopyrone lactone
polyphenols,Rosmarinic acid,completed,4c8aae8f-b676-47cc-9c49-95a983f0b44a,5dd161b3-0f4a-4984-a77e-168e0496163e,1.7767,1.8417,,,,,,,,,,,,,,,Moderate after oxidation,catechol rich polyphenol
polyphenols,Fisetin,completed,a826fcae-39d1-4a1a-89b4-345f62cbf1ee,6e7bc995-1bf3-4f13-b880-268989019808,1.8286,1.8208,,286.048,1,6,4,0,0,2.282,111.13,231.44,0.816,,,,Moderate after oxidation,flavonol oxidizable polyphenol
polyphenols,Naringenin,completed,dd7c9d10-e5a6-4f8b-84f6-16af3e307300,90449a22-7264-49b9-9f89-1b677074dd1a,1.6694,1.6335,,272.068,1,5,3,0,0,2.51,86.99,228.64,0.653,,,,Moderate after oxidation,flavanone
polyphenols,Xanthohumol,completed,04300fbf-48d7-421c-916b-9f92ecf83a70,39364397-96c3-416d-92d5-9f0eba1743b2,1.808,1.7614,,354.147,6,3,3,0,0,4.217,66.76,317.336,0.384,,,,Moderate-high,prenylated chalcone
polyphenols,CAPE,completed,7b768300-44d5-4c24-a191-9678d3bbb29d,3aed9c12-3ba9-452c-8adc-c488c2ef91f4,1.8083,1.2163,,284.105,5,4,2,0,0,2.897,77.76,317.336,0.384,,,,Moderate,caffeic acid phenethyl ester
tea_polyphenols,Theaflavin,completed,124991a7-7124-4082-ab7f-caa815546076,6c8b4a95-e023-485d-aaf9-7f27a68ad5a3,2.5523,2.0905,,564.127,2,12,9,0,0,2.213,217.6,454.808,1.48,,,,Moderate after further oxidation,oxidized tea dimer
tea_polyphenols,Theasinensin A,completed,a73afd5e-94ab-4fdb-99a1-86c85ec13b7f,e60f1881-c011-4e69-80c2-71387c892191,2.0051,1.8405,,914.154,7,22,16,0,0,4.447,394.74,718.424,2.904,,,,Moderate after further oxidation,oxidized tea oligomer
tea_polyphenols,Oolonghomobisflavan B,completed,6c81a1a7-fbbb-40b8-90a3-75ad15208891,3b72b4c0-0552-4fc4-ab94-c696bba667a4,1.7163,1.8924,,928.17,8,22,16,0,0,4.371,394.74,737.896,2.897,,,,Moderate after oxidation,oolong oligomeric polyphenol
sulfur_compounds,Modafinil sulfone,completed,803ca752-da4a-489d-bc07-41a7b0851359,2a35ecd0-ebf5-4878-a059-25454277e5e1,1.6411,1.5722,,,,,,,,,,,,,,,Moderate,sulfone scaffold
sulfur_compounds,Modafinil,completed,c30391e3-85e1-42f3-a5a5-a6fed144b712,dab4dad7-2017-454d-99b7-a97e2d2b5500,1.48,1.4155,,,,,,,,,,,,,,,Moderate,sulfoxide carboxamide
sulfur_compounds,Glutathione,completed,4bca5d13-512a-4835-aea8-79b2d1ba6d08,7a1bd992-7687-4198-86e5-64db14855337,1.328,1.1971,,,,,,,,,,,,,,,Low direct,redox buffer thiol trap
sulfur_compounds,Sulforaphane,completed,a5b1fa29-8159-42c5-bb94-9aa04d5bc6ba,bf8f2057-e120-484d-ba14-5f7a68fa3b8e,1.164,0.9056,,177.028,5,3,0,0,0,1.248,35.42,157.56,0.713,,,,High via NCS,isothiocyanate thiol chemistry
sulfur_compounds,Allicin,completed,f40de8f7-9140-402d-bf83-c5cec323ee6c,acb7c3a2-a044-47ed-9498-2dcfc57c39f4,1.1139,,,,,,,,,,,,,,,,Moderate non Michael,thiol reactive sulfur electrophile
sulfur_compounds,Cysteine,completed,e2a39622-d2f2-44d9-b3a8-0178af3de2b2,197a5678-af59-4f6e-ab1e-38c472dff083,0.8667,0.6722,,,,,,,,,,,,,,,Low,nucleophilic thiol
sulfur_compounds,Homocysteine,completed,4ce7a0e4-b337-4c82-8635-865bd85c8423,834bf683-2ff6-48aa-9320-cfd2f408e884,0.7396,0.6891,,,,,,,,,,,,,,,Low,nucleophilic thiol
sulfur_compounds,Ergothioneine,completed,fd646e03-ab09-48f2-8063-6556a0bc4d5a,07b7daa0-1e99-462f-a7e6-1d04018ba497,0.6548,0.6266,,229.088,4,3,2,1,1,-0.561,103.8,203.344,0.381,,,,Low direct,thione thiol antioxidant
sulfur_compounds,DMSO,queued,1876d470-a6a1-4e2f-aad8-f7ace03fa7f3,914b8706-4d7f-492a-b751-b948859476cf,,,,"",,,,,,,,,0,1,,Low direct,polar sulfoxide solvent
garlic_sulfur,Ajoene,awaiting_queue,c8a474e6-a973-489a-8c27-b83a5b9a6c1e,9500a51e-66f9-4d91-a340-328d87ac0d5e,,,,,,,,,,,,,,,,thiol reactive sulfur electrophile
garlic_sulfur,Diallyl disulfide,awaiting_queue,392da6eb-63dd-41fa-b7f7-ce62ddce0acb,6ec5344c-3d23-4876-a09e-045af81c503c,,,,,,,,,,,,,,,,garlic sulfur comparator
garlic_sulfur,Diallyl trisulfide,awaiting_queue,e1481b34-6607-4252-9a95-bbe52e0b1e6d,837d2ab4-6209-4cf1-9682-6298179ffb22,,,,,,,,,,,,,,,,garlic sulfur comparator
psychoactives,Ketamine,completed,03556844-cece-4e19-9bc6-f0b0b84acba2,19bd6ead-92b1-48a1-a44c-be2062b2628d,1.2822,1.1107,,,,,,,,,,,,,,,Low-moderate,aryl cyclohexanone
psychoactives,LSD,completed,b88504bc-c90e-49bd-927a-a9e1187fbb3f,eb76525b-467f-4fec-b3ff-5269a431a7f8,1.1876,1.095,,,,,,,,,,,,,,,Low-moderate,ergoline indole alkaloid
psychoactives,Methoxetamine,completed,a3c4e49b-c0c7-49e3-9596-223ab5dee03f,f18e3adc-d467-4bc6-aa72-9053c68ec273,1.1167,1.0786,,,,,,,,,,,,,,,Low-moderate,aryl cyclohexanone
psychoactives,5-MeO-DMT,completed,66ab86e8-de09-4349-9393-4cf01e16ce98,f5ed1bf7-56a2-410e-af5c-16c27016dc54,0.8288,0.8735,,,,,,,,,,,,,,,Low,methoxy tryptamine
psychoactives,DMT,completed,1eefa4d6-0f20-41c1-b0b1-2b43be207a12,69370c05-179a-4b2a-980e-8150af013e27,0.8919,0.8372,,,,,,,,,,,,,,,Low,indole amine
psychoactives,2C-I,completed,39edcaff-870f-4c97-a9a3-a463393a4e08,f5631197-0bc8-4709-97f9-3d6784b5350f,0.8295,0.7159,,,,,,,,,,,,,,,Low,iodinated phenethylamine
catecholamines,Norepinephrine,completed,dfaf3b8b-2ec9-4643-b4b4-47d5b5f4463a,29c13e02-0392-4649-acd1-5e55c55a15f5,0.7839,0.8106,,169.074,2,4,4,0,1,0.09,86.71,153.704,0.321,,,,High after oxidation,catecholamine
catecholamines,Dopamine,completed,2493f7b9-4882-46d5-8ade-d37c8ee3f7b5,9b9f925e-eff4-41b0-b456-d92c6e4f4146,0.8095,0.8045,,,,,,,,,,,,,,,High after oxidation,catecholamine
indoles_melatonin,AFMK,completed,a488bc80-5c7c-409d-a13c-f84987f3df9a,d37c5e49-bb8d-44b9-a750-2e6501325775,1.0762,1.123,,275.127,6,3,3,0,0,1.423,83.22,249.424,0.623,,,,Low-moderate direct,oxidized melatonin kynuramine
indoles_melatonin,Melatonin,completed,542b024d-e90a-4434-a872-2707654cdf86,1679243c-34cb-4815-a567-080c669433f3,1.0491,1.0437,,232.121,4,2,2,0,0,1.855,54.12,218.928,0.429,,,,Low-moderate direct,indole amide antioxidant
indoles_melatonin,6-Hydroxymelatonin,completed,ad4881e5-4162-45b3-a421-27c05309c5a1,a38dfcfb-dde3-4386-9eb0-256631420041,1.0616,0.9797,,248.116,4,3,3,0,0,1.561,74.35,226.992,0.475,,,,Low direct,phenolic oxidized melatonin metabolite
indoles_melatonin,Cyclic 3-hydroxymelatonin,completed,b749ddaa-1d9d-4a8e-a5b5-a387733be69b,180052ae-1b1d-41a8-88ee-cabec8d52f4c,1.029,0.9364,,248.116,1,4,2,0,0,0.887,61.8,223.336,0.343,,,,Low direct,cyclized hydroxymelatonin metabolite
hormones,Testosterone,completed,0ff740bd-2fc3-4084-9835-c2cbe88081f6,1eb0bb62-62ef-4740-a2d1-c2e1440662ae,1.1186,0.8674,,288.209,0,2,1,0,0,3.879,60.69,274.592,0.311,,,,Low-moderate direct,nonaromatic androgen
hormones,Estradiol,completed,bb0dbd78-f5a2-424e-af78-9d3f30e2374e,c00f50cb-eeb7-48a9-bc1e-fb906e0539b6,1.6687,0.8323,,288.173,0,3,3,0,0,3.315,60.69,274.592,0.311,,,,Moderate-high after oxidation,phenolic estrogen
hormones,Estrone,not_resolved,,,,,,,,,,,,,,,,,,Moderate-high after oxidation,phenolic estrogen
other_natural_products,Zeaxanthin,completed,f479ba2f-2605-41b2-ba4a-a8c62101037a,9268f8e1-ed7e-4467-96ee-280f4e4e031b,2.5428,2.8094,,568.89,,,,,,,,,,,,Low direct,intact bulky polyene
other_natural_products,Lutein,completed,ab4be108-3413-4a0e-bec9-a2a77fc1b371,89addb12-1c35-49f7-9e5e-3f5bdee63aa5,2.4511,2.6915,,568.89,,,,,,,,,,,,Low direct,intact bulky polyene
other_natural_products,Cinnamaldehyde,completed,e259f631-cab3-48f6-8fb4-e5e48bf0fea2,84eecbec-de6d-49bf-b9af-3e885e948cc7,1.946,1.9567,,132.058,2,1,0,0,0,1.899,17.07,130.344,0.365,,,,High,alpha beta unsaturated aldehyde
other_natural_products,Erinacine A,completed,b9c6dca0-7592-4ae3-a7de-f21ce8455eea,6900e957-9d3e-4e08-8f77-b0c1eb0d1d63,1.8941,1.8941,,432.251,4,6,3,0,0,2.819,96.22,,,,,Moderate-high,oxygenated diterpenoid glycoside
other_natural_products,Piperine,completed,74247ec9-eeab-460c-bdf8-f16aee92ebee,b1135278-c412-42ef-8254-cec9c0086c77,1.6063,1.7911,,,,,,,,,,,,,,,Moderate,conjugated amide
other_natural_products,Bergamottin,completed,f8065874-917f-4177-953b-bb15f0554fac,5fadfebb-44a0-40b0-a4e0-a218f5e2a996,1.7923,1.6782,,338.152,6,4,0,0,0,5.611,52.58,412.88,0.636,,,,Moderate,bulky furanocoumarin
other_natural_products,Cinnamic acid,completed,ab53b439-bc4b-42b8-999a-2bfc279a3aad,d2d10a59-a985-45aa-a7c0-ae5dc7bf4513,1.592,1.6497,,148.052,2,1,1,1,0,1.784,37.3,138.376,0.414,,,,Moderate,conjugated acid
other_natural_products,Piperonal,completed,38fbf92d-f75d-400b-815f-faf158d1f418,b482f27a-c468-4c35-8332-fe58499a880f,1.6215,1.5869,,,,,,,,,,,,,,,Moderate,compact aromatic aldehyde
other_natural_products,Retinoic acid,completed,20927e66-60df-4c48-b662-cbb9ad99645e,c2f6d294-13fb-4545-ad9d-b3b1057e6298,2.2685,,,,,,,,,,,,,,,,Moderate-high,conjugated retinoid acid
other_natural_products,alpha-Tocopheryl quinone,completed,,7ca7faf9,2.7604,,,,,,,,,,,,,,,,Moderate-high,bulky quinone
other_natural_products,alpha-Tocotrienol,completed,,,1.1063,0.9909,,,,,,,,,,,,,,,Low-moderate,bulky antioxidant chromanol
other_natural_products,alpha-Tocopherol,completed,,,0.8231,0.7886,,,,,,,,,,,,,,,Low,radical terminating chromanol
other_natural_products,Oleanolic acid,completed,ba4b83c6-7866-4f94-8cab-5d3c975f6846,4073491c-7d54-4183-adeb-19c6922f3a61,,0.8586,,456.36,1,,,,,,,,,,pKa ~4.30,Low,rigid pentacyclic acid
other_natural_products,Limonene,completed,d7aa1eaa-7f02-41f4-9fa6-bcdb814bb312,bc90030a-4e07-4468-aa3d-0c6710727c10,0.7771,0.7462,,136.125,1,0,0,0,0,3.309,0,155.664,0.123,,,,Low,terpene hydrocarbon
other_natural_products,6-Shogaol,completed,ff547cef-a1e9-4a5b-9b7f-dcefb1a03520,02178f7d-d1ef-4308-becd-207dbd822e6d,1.5346,,,,,,,,,,,,,,,,High,alpha beta unsaturated ketone
other_natural_products,Capsaicin,completed,66da5a9e-6ae1-4e9f-bb49-649f7f672e46,ee0e5259-c01f-4b50-8f22-ae587de49668,1.0897,1.027,,305.199,9,3,2,0,0,3.79,58.56,308.96,0.661,,,,Low-moderate direct,vanillyl amide
other_natural_products,Dihydrocapsaicin,completed,6b6f836b-b05c-4cff-b3f7-260358c94365,56adedaf-66e5-471a-9da6-ab96b2d26a15,0.9585,0.8962,,307.215,10,3,2,0,0,4.014,58.56,314.992,0.615,,,,Low-moderate direct,vanillyl amide
other_natural_products,6-Gingerol,completed,1b003dca-22a5-499a-9671-3f44a5e216cd,71a8eb44-ece7-4add-9075-ad524cd8a17b,1.2653,1.0922,,294.183,10,4,2,0,0,3.234,66.76,295.592,0.641,,,,Moderate direct,ginger ketol
misc,Theabrownin,not_single_molecule,,,,,,,,,,,,,,,,,,Mixture heterogeneous,polymeric tea oxidation fraction
plasmalogens,PC plasmalogen omega-3 representative,running,a7d80c2f-fae5-4c16-88fe-47553c5ac1c7,7d34d8bf-a8a7-4a91-afb3-bb59abf563cb,,,"C46H80NO7P",790.12,,,,,,,,,0,1,,Low direct; oxidation fragment risk,plasmenylcholine DHA representative
plasmalogens,PC plasmalogen omega-9 representative,running,c0adaf02-a795-4077-a0a3-cf97f479d469,839d7049-5d87-4efb-abaa-7e179c62080f,,,"C42H82NO7P",744.09,,,,,,,,,0,1,,Low direct; oxidation fragment risk,plasmenylcholine oleoyl representative
plasmalogens,PE plasmalogen omega-3 representative,mixed,40c5a795-e158-4f98-8481-ca835ee1d145,8dad446c-3bd7-40b3-a90d-eb2bdba9d219,,,"C43H74NO7P",748.04,,,,,,,,,0,1,,Low direct; oxidation fragment risk,plasmenylethanolamine DHA representative
plasmalogens,PE plasmalogen omega-9 representative,awaiting_queue,0aea705c-fdb1-4fe1-8a77-5e58dd6f599e,f88f9240-eb2d-4dcf-82b4-e683ac01c3ad,,,"C39H76NO7P",702.01,,,,,,,,,0,1,,Low direct; oxidation fragment risk,plasmenylethanolamine oleoyl representative
sesquiterpene_lactones,Parthenolide,awaiting_queue,233761f1-6459-4d89-9ad6-ff7bc551edcb,51f3c5a4-5c9c-41c8-8c99-edccba8a9bc7,,,,,,,,,,,,,,,,alpha methylene gamma lactone
sesquiterpene_lactones,Helenalin,awaiting_queue,7f6d6c0d-9a26-4f56-a1a6-b57d7b904a4c,4b457443-5992-4e79-b0ba-8696687f6d21,,,,,,,,,,,,,,,,alpha methylene gamma lactone plus enone
sesquiterpene_lactones,Costunolide,awaiting_queue,ba5f7602-e2dd-4a9e-986c-d76b7c370740,dd088c9a-005e-4a7b-b744-8b1362b1382d,,,,,,,,,,,,,,,,alpha methylene gamma lactone
sesquiterpene_lactones,Dehydrocostus lactone,awaiting_queue,7617840c-b6fa-432b-9123-fd8f6f223e78,852ed45b-ec01-4739-b6f9-0d46778ab8a1,,,,,,,,,,,,,,,,alpha methylene gamma lactone
sesquiterpene_lactones,Deoxyelephantopin,completed,87521a1f-1c85-45d3-bbb6-1b58e1104b3b,c1925be3-e940-4997-bb92-dcd3fac14497,2.1196,2.4419,,344.126,2,6,0,0,0,2.164,78.9,306.2,0.732,,,,High direct,sesquiterpene lactone
sesquiterpene_lactones,Alantolactone,completed,6e8aefcc-e04c-4e62-aae5-138a512bd9ad,33c93ed8-799a-4be3-8225-cc41eaab5ff7,1.3286,1.4033,,232.146,0,2,0,0,0,3.241,26.3,229.008,0.232,,,,High direct,sesquiterpene lactone
withanolides,Withaferin A,awaiting_queue,0a754189-c768-4ee1-8976-09e562ebab06,48c0804c-54b0-41ca-b89b-839ed259fc04,,,,,,,,,,,,,,,,epoxy enone withanolide
withanolides,Withanone,awaiting_queue,f3996973-e956-42b4-91b0-6423657bd09c,6a98be11-1359-48a5-a8ab-b0037793c77b,,,"C28H38O6",470.61,,,,,,,,,0,1,,enone withanolide
isothiocyanates,Allyl isothiocyanate,awaiting_queue,60553a41-f39a-426a-954f-63274fd8c592,3c972d84-6aa5-4745-914e-d806c1bf64ef,,,,,,,,,,,,,,,,isothiocyanate
isothiocyanates,Benzyl isothiocyanate,awaiting_queue,e66a10e0-f88b-4fef-8eeb-64dca1724088,8cb68e27-28f5-4746-b1bd-4c640bc25ab2,,,,,,,,,,,,,,,,isothiocyanate
isothiocyanates,Phenethyl isothiocyanate,awaiting_queue,1beb42ff-6745-4bf4-8aca-55c82653b56b,7f6654c0-5a16-4585-87da-928d501d7b12,,,,,,,,,,,,,,,,isothiocyanate
quinones_catechols,Zerumbone,awaiting_queue,a60c63a0-8319-40b8-b510-f27cf309ba10,31855294-4373-4bbe-88ce-3e3af093ad0a,,,,,,,,,,,,,,,,sesquiterpene enone
quinones_catechols,Juglone,awaiting_queue,8d4db96a-4dca-485a-9237-3d4fe776aa8f,ceb82e14-d4a3-4686-af7c-d6f52e2c6db3,,,,,,,,,,,,,,,,naphthoquinone
quinones_catechols,Lawsone,awaiting_queue,1f153ffa-80ab-4700-9d08-7821df413e52,57454766-f1f1-43bf-9f8b-59d0f048987a,,,,,,,,,,,,,,,,naphthoquinone hydroxy
quinones_catechols,Plumbagin,awaiting_queue,794ef7bb-6eb6-43c5-ba5d-c77871064009,6efc1f1a-6db8-401b-8bb9-9de24316ed5f,,,,,,,,,,,,,,,,naphthoquinone
quinones_catechols,Lapachol,awaiting_queue,f3f64ca1-0998-433a-8e37-70e5b8d72e4d,7b9bf6c9-fe39-4beb-96fe-620ff39e3f96,,,,,,,,,,,,,,,,prenylated naphthoquinone
quinones_catechols,Beta-lapachone,awaiting_queue,0534a1a4-a919-446b-b6ea-347ff4d46a96,a2fe6dfc-1f75-46d9-8c19-d184cb815338,,,"C15H14O3",242.27,,,,,,,,,0,1,,lapachone quinone
quinones_catechols,Caffeic acid,awaiting_queue,e42bb3de-a25b-47b3-8b5e-4360ea457e18,03c3bb26-3c6f-4ac1-b674-bb0059f50b16,,,,,,,,,,,,,,,,catechol cinnamate
quinones_catechols,Chlorogenic acid,awaiting_queue,4ae57051-0fd2-4a81-806d-0d7928399407,fbdfae54-a727-46ae-9604-b69ae7763c31,,,,,,,,,,,,,,,,caffeoyl quinic acid
quinones_catechols,Gallic acid,awaiting_queue,3f0841af-20d8-4ee4-9a5d-37fde4c435e8,957fda98-837f-45de-ab88-0ddda111739c,,,,,,,,,,,,,,,,pyrogallol acid
quinones_catechols,Hydroxytyrosol,awaiting_queue,79af055b-9be0-4f2b-a30c-fc1ef7f5a698,93b1a693-4be3-4f86-836f-4474b4a8915e,,,,,,,,,,,,,,,,catechol alcohol
quinones_catechols,Hydroxychavicol,awaiting_queue,f0ecd910-210b-46e8-b473-9f6c7e1c6276,4e07c187-f603-43d1-b1aa-a392886abf1b,,,,,,,,,,,,,,,,allyl catechol
quinones_catechols,Thymoquinone,completed,7f931f9c-84c3-49bc-9471-3c2de79c04d6,798d64cd-9bc6-4ef9-9a13-62e9183ba348,2.6866,2.7863,,164.084,1,2,0,0,0,1.667,34.14,257.472,0.68,,,,Very high,p benzoquinone natural product
quinones_catechols,Shikonin,completed,38d1c2fd-c015-4b2a-b365-81925de25abf,f1293107-0533-4f74-b70d-66d6de033911,2.9994,1.8722,,288.1,3,5,3,0,0,2.12,86.99,325.84,0.887,,,,High direct,naphthoquinone natural product
quinones_catechols,Carnosic acid,completed,1833b51a-cf93-44f9-9ff4-48a8e560cfff,6ca28a3b-8b76-46f8-b879-4fba5a0efeaa,1.0104,1.2345,,332.199,2,4,2,1,0,4.316,66.76,308.608,0.359,,,,Moderate after oxidation,oxidizable diterpene phenol
quinones_catechols,Carnosol,completed,b8368d3a-b48c-4fc3-80bb-ab372a8b06be,c8cfb3bc-46fd-4198-9b56-82b2c3db3b27,1.1528,2.9314,,330.183,1,4,2,0,0,4.287,78.9,294.696,0.232,,,,High direct,oxidized diterpene phenol
quinones_catechols,Embelin,completed,d5f87f91-2baf-40d1-8e51-b013acd3b696,4f8bd077-d18a-4241-aa3a-1a8846fed455,2.7744,1.4033,,294.183,10,6,0,0,0,4.313,26.3,229.008,0.232,,,,High direct,alkyl benzoquinone
protective_comparators,Ascorbate,awaiting_queue,6375b6fe-24aa-49cd-a9f6-20ab7a5ba518,1bd3f295-8576-4c67-9dd0-34dcc4095300,,,,,,,,,,,,,,-1,1,,trap control antioxidant
protective_comparators,Urate,awaiting_queue,861fa8c9-d90d-408d-af4d-c0ef50e89ad3,ba8b896f-31eb-4a5c-8002-bd044a15a437,,,,,,,,,,,,,,,0,1,,trap control antioxidant
protective_comparators,Ovothiol,awaiting_queue,4383323e-a016-457c-b183-80ee74f1bca5,5fd17127-c72a-4547-b931-91c43985ed42,,,,,,,,,,,,,,,0,1,,thiol antioxidant comparator
protective_comparators,Carnosine,awaiting_queue,e0f0e5f0-ad47-46a1-befa-3056fcc66b65,b82e6f95-ca78-4311-9e4f-8287b8c8cd7d,,,,,,,,,,,,,,,0,1,,carbonyl trap comparator
triterpenoid_quinone_methides,Celastrol,completed,b43e04f7-e2c9-4b68-bcfe-f8d3b929f9ca,a3ef65cf-8d41-4abd-994e-52293c48c710,2.3403,2.4089,,450.277,1,4,2,1,0,6.698,74.6,432.832,0.477,,,,High direct,quinone methide triterpenoid
coffee_metabolites,Quinic acid,completed,2df03199-0502-4b13-9f88-127e418f33fb,c0ab2652-ab99-45c9-9f3c-faaacd18aaf4,0.9997,0.8172,,192.063,1,5,5,1,0,-2.321,118.22,161.376,0.344,,,,Low direct,polyol acid metabolite
coffee_metabolites,Ferulic acid,completed,515fa325-ea78-4812-ae4a-55e1b0e399e2,2171bd8a-64a1-4ea7-8e03-174db18b540c,1.6523,1.7197,,194.058,3,3,2,1,0,1.499,66.76,172.056,0.543,,,,Moderate after oxidation,methoxy phenylpropanoid acid
coffee_metabolites,Isoferulic acid,completed,9c3b709e-0060-4819-b4e9-76624dd2000c,eaa67d54-98b6-4b6c-9eca-9c7a00ee5bda,1.6555,1.7222,,194.058,3,3,2,1,0,1.499,66.76,172.36,0.543,,,,Moderate after oxidation,methoxy phenylpropanoid acid
coffee_metabolites,Dihydrocaffeic acid,completed,174f3875-d66a-4dc0-ae18-99ec8c7680e7,2a52c99c-9bae-4fdb-993b-eb196a64d18a,1.1191,1.0119,,182.058,3,3,3,1,0,0.796,77.76,160.912,0.436,,,,Moderate after oxidation,reduced catechol acid
coffee_metabolites,Dihydroferulic acid,completed,b7814148-53df-4733-96a7-3919b453c7d5,e8dad5d4-7e7b-4732-bf15-eeefa9d5d783,1.1359,1.0239,,196.074,4,3,2,1,0,1.418,66.76,178.128,0.46,,,,Moderate,reduced methoxy phenylpropanoid acid
coffee_metabolites,Protocatechuic acid,completed,55ea2830-fb4b-4a10-bca5-a0a50538967e,9826c1b1-3d67-442a-b763-840aeff1da72,1.4587,1.4223,,154.027,1,3,3,1,0,0.796,77.76,127.736,0.401,,,,Moderate after oxidation,catechol benzoic acid
coffee_metabolites,Vanillic acid,completed,0a95c630-60b0-4ef3-b4f8-1f096329d3b6,96511d95-f996-413c-989d-26c0dd28aff1,1.4154,1.3662,,168.042,2,3,2,1,0,1.099,66.4,144.12,0.415,,,,Moderate,methoxy benzoic acid
coffee_metabolites,Homovanillic acid,completed,34ebb04b-239b-4ed5-a2f4-390a7578f944,855ee56b-9836-4ff6-973b-d6f944aa7c91,1.5221,1.0319,,182.058,3,2,2,1,0,1.028,66.4,159.08,0.548,,,,Moderate,phenolic acid metabolite
coffee_metabolites,Hippuric acid,completed,26e8e09a-a156-4b86-a195-28f4938320de,b81ce715-feff-4a3a-9523-04a1da75892d,1.5221,1.4663,,179.058,3,2,2,1,0,0.501,66.4,159.08,0.548,,,,Low direct,aromatic amide acid metabolite
coffee_metabolites,Trigonelline,completed,caffdf1b-6f17-4bdd-a742-e63fb6ca9177,b56cb6ff-520f-4bfd-8805-40a0ba87d6ce,1.9147,1.9147,,137.048,1,2,0,1,1,-1.125,44.01,124.04,0.298,,,,Low direct,zwitterionic alkaloid metabolite
polycyclic_aromatics,Naphthalene,completed,580e3b90-1a63-4b19-ac3e-ca4096f0b84a,9eb51075-ef4f-479e-bbc8-9c745ad90b33,1.405,1.3355,,128.063,0,0,0,0,0,2.84,0,126.672,0.196,,,,Low direct,polycyclic aromatic hydrocarbon
polycyclic_aromatics,Anthracene,completed,b8cce4e7-431a-4ebe-af44-9989fb1575d8,f61dd230-7d8a-4a31-a014-2d5c39c07dde,1.818,1.7123,,178.078,0,0,0,0,0,3.993,0,170.256,0.309,,,,Low direct,polycyclic aromatic hydrocarbon
fatty_acids,Oleic acid,completed,b7d39df4-e588-411b-9e5b-c560f45eda86,d7ec7eed-a579-4cdf-baa8-b85e502953e0,1.055,0.8583,,282.256,15,1,1,1,0,6.109,37.3,317.856,0.704,,,,Low direct; oxidation fragment risk,MUFA fatty acid
sweeteners,Sucralose,completed,7b505233-d7f0-4929-b646-74d3ae783553,6cd5ecde-fabd-4dd5-9a08-0b45e85aef96,0.8583,0.8574,,396.015,5,3,2,0,0,-1.656,74.6,432.832,0.477,,,,Low direct,chlorinated sweetener
saffron_phytochemicals,Crocetin,queued,ab794b04-08e9-4752-ab12-7b7a8eb0599f,848d31e5-a0c2-4296-8018-1e7e044aef19,,,,,,,,,,,,,,,0,1,,Moderate,apocarotenoid dicarboxylic acid
saffron_phytochemicals,Cresol,queued,ec72df59-5564-43ed-a207-bb1c284e9bb2,1558cfa7-26c9-4a33-937b-822be2d4eeb3,,,,,,,,,,,,,,,0,1,,Low-moderate,phenolic cresol literal resolution