https://x.com/AriWagen?t=z2TT_XA27K_JVk0rrdmz6Q&s=09
https://twitter.com/AriWagen/status/1773083391702847863
they’re very responsive
CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
It is ridiculously easy to now (via codex) analyze the reactions of EVERY SINGLE PLANT METABOLITE against the downstream metabolites of dopamine [and their pereferred charge states] you want to “clean up” if you have excess DOP that you’re not cleaning up due to ur defecttive asian quinone reductase variant.
[and then feed in the remaining tautomers/charged states of the metabolites that can then be “fit against” GST or other cleanup enzymes
[or every single plant metabolite and carotenoid against 8oxog]
[still MANY CAVEATS APPLY and this is not perfect but this still works as a first pass and is WAY BETTER than anything we had b4
For rapamycin at GFN2-xTB, the global electrophilicity index came out to 1.342, which is moderate: it is not a uniformly “hot” electrophile, but it does have strongly polarized local regions. The strongest condensed Fukui f+ signal, which points to sites most responsive to nucleophilic attack, clusters in three oxygen-rich neighborhoods rather than on a single isolated atom:
- the carbon/oxygen pair around atoms 13-14 in Rowan’s atom order (f+ ~ 0.0515 on C and 0.0941 on O),
- a second oxygenated center around atoms 40-41 (f+ ~ 0.0255 on C and 0.0508 on O),
- a third around atoms 52-53 (f+ ~ 0.0251 on C and 0.0503 on O).
That pattern is what I’d expect for rapamycin: the most electrophilically responsive density is concentrated in its carbonyl/ester/hemiketal-rich substructures, with the condensed charge partitioning smearing reactivity over adjacent C/O pairs. Practically, this means “reactive spots” are best interpreted as carbonyl-adjacent oxygenated motifs, not as a single atom with a clean textbook label.
The strongest condensed Fukui f- signal, which points to sites most responsive to electrophilic attack, is again dominated by oxygen-rich and unsaturated regions:
- oxygen-centered sites around atoms 53, 36, 14, 34, 16, 50,
- carbon-rich contribution around atoms 64, 59, 62, 61.
So the electron-rich side of the molecule is spread across the oxygen network plus parts of the conjugated/more polarizable macrocycle. Physically, that says rapamycin behaves less like a compact aromatic electrophile and more like a soft, conformationally distributed, oxygen-polarized macrocycle where local electrostatics and conformation will matter a lot.
The frequency job c1271495-d2c0-4adc-bfb1-f2ede954d281 is still RUNNING. Once that finishes I can give you the actual dominant bending/breathing/torsional modes and connect them to the Fukui map.
==
- Warning: Rowan reported a small imaginary frequency, meaning the optimized structure is very close to, but not exactly at, a true minimum on the PES.
What I could extract:
- The final single structure energy from the high-level single-point stage was -3022.897615
- The xTB optimization/frequency stage completed and the overall workflow consumed 58.89 credits
What I could not extract through the current Rowan MCP:
- The actual list of vibrational frequencies
- The normal mode displacement vectors
So I can’t honestly give you the literal “top 5 modes at X, Y, Z cm-1” from this interface alone.
What the warning likely means, as an inference:
- Rapamycin is a very floppy macrocycle, so the lowest modes are almost certainly soft macrocycle torsions, breathing, and hinge-like bends.
- The small imaginary mode is probably one of those near-flat conformational coordinates rather than a chemically meaningful bond-breaking direction.
Connection to the Fukui map, as an inference:
- The Fukui hotspots were concentrated in oxygen-rich carbonyl/ester/hemiketal regions.
- Low-frequency macrocycle bending should mainly modulate exposure, alignment, and polarization of those same motifs rather than shift reactivity to a completely different part of the molecule.
- In other words, rapamycin’s reactivity is probably conformation-gated: the macrocycle motions change how accessible those pre-existing electrophilic/electron-rich regions are.
The vibrational run is finished, and I can now tie the actual low-frequency modes to the Fukui map.
Modes
There is one small imaginary mode at -7.121 cm^-1. Rowan flagged this explicitly, so treat it as a floppy near-free coordinate, not a chemically meaningful instability. For a macrocycle this size, that is usually a shallow torsional/breathing coordinate.The lowest real modes are:
- 3.204, 6.549, 9.830, 12.418, 14.150, 18.115, 18.635, 21.328, 25.702, 28.841, 32.005 cm^-1
Among these, the strongest low-frequency IR-active modes are:
- 18.115 cm^-1 with IR intensity 1.05
- 25.702 cm^-1 with IR intensity 0.975
- 32.005 cm^-1 with IR intensity 0.713
These are the main soft collective motions, and they are exactly in the macrocycle bending / torsion / breathing regime.
Fukui Connection
The strongest Fukui f+ atoms were 14, 13, 41, 53, 16, 40, 52, with atom 14 the largest by far. The strongest f- atoms were 53, 36, 64, 140, 141, 14, 138, 59, 34.What matters is that several of those same atoms participate strongly in the soft modes:
- Atoms 34 and 36 are strongly involved already in the 3.204 cm^-1 mode.
- Atom 41 is active in the 9.830 cm^-1 mode.
- Atom 53 is strongest in the 14.150 cm^-1 mode.
- Atoms 13, 14, and 16 become more active in the 18-32 cm^-1 band.
- Atoms 138, 140, and 141 also pick up strongly in the 25.702-32.005 cm^-1 region.
So the mechanistic read is fairly clean: rapamycin’s soft macrocycle motions are not random peripheral floppiness only. They directly modulate several of the same oxygen-rich, Fukui-active regions that carry the strongest local electrophilic/electron-rich response.
Interpretation
The physically useful picture is:
- 3-14 cm^-1: very soft hinge/torsional motions, including an oxygenated hotspot around atoms 34-36 and another around 41.
- 14-18 cm^-1: bending/twisting starts to engage the 53 region and begins coupling more clearly into the reactive oxygen network.
- 18-32 cm^-1: the most important low-frequency band for conformation-gated reactivity. This is where the 13/14/16, 53, and 138/140/141 hotspot regions are all being modulated appreciably.
So the conclusion is that rapamycin looks conformation-gated rather than statically reactive: the Fukui hotspots are real, but the lowest macrocycle bending/torsional modes likely control how exposed and polarized those hotspots are at any given instant.
I also submitted a cleaner rerun, 8841f67d-4713-4d40-8277-13c54467c17f, to see if Rowan can remove the small imaginary mode. If you want, I can follow that one too and compare whether the low-mode pattern is stable.
Rapamycin’s electronic reactivity is concentrated in a small number of oxygen-rich motifs rather than spread uniformly across the macrocycle. The strongest condensed Fukui f+ response is centered on the 13-16, 40-41, and 52-53 regions, consistent with carbonyl/ester/hemiketal-type electrophilic polarization. The strongest f- response overlaps partly with those same oxygenated sites and extends into a few more polarizable macrocycle positions, indicating that the molecule’s most chemically responsive regions are clustered around its dense heteroatom network rather than the hydrocarbon backbone.
Its lowest vibrational modes are very soft collective motions: one small imaginary mode at -7.1 cm^-1, then real modes at roughly 3-32 cm^-1. These are not localized bond stretches; they are macrocycle torsions, hinge bends, and breathing-like deformations. Critically, several Fukui-active atoms participate appreciably in those same low-frequency modes, especially around the 34-36, 40-41, and 52-53 regions, with the 13-16 hotspot joining more strongly in the 18-32 cm^-1 band. The practical mechanistic picture is that rapamycin is conformation-gated: its main reactive oxygen-rich motifs are intrinsic electronic hotspots, but the soft macrocycle motions likely regulate how exposed, aligned, and polarized those hotspots are at any moment.
csv format, feel free to c/p into your fav LLM
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