Identification

PhytoHub ID
PHUB002396
Name
Ergothioneine
Systematic Name
(2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Synonyms
  • 2 Thiol L histidine betaine
  • 2-Thiol-L-histidine-betaine
  • Ergothioneine
  • Thioneine
CAS Number
497-30-3
Average Mass
229.3
Monoisotopic Mass
229.088497909
Chemical Formula
C9H15N3O2S
IUPAC Name
(2S)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
InChI Key
SSISHJJTAXXQAX-ZETCQYMHSA-N
InChI Identifier
InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
SMILES
C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O
Structure

Calculated Properties

Solubility (ALOGPS)
5.94e-02 g/l
LogS (ALOGPS)
-3.68
LogP (ALOGPS)
-1.72
Hydrogen Acceptors
2
Hydrogen Donors
2
Rotatable Bond Count
4
Polar Surface Area
64.19
Refractivity
84.8711
Polarizability
23.45377825134843
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
Not Available
pKa (strongest acidic)
3.489266415614524
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
N-containing compounds
Class
Amino acids
Sub-class
Not Available

Taxonomy as Metabolite

Metabolite Family
N-containing compound metabolites
Metabolite Class
Amino acid metabolites
Metabolite Sub-class
Not Available

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Carboxylic acids and derivatives
Super-class
Organic acids and derivatives
Sub-class
Amino acids, peptides, and analogues
Direct Parent Name
Histidine and derivatives
Alternative Parent Names
["Aralkylamines", "Azacyclic compounds", "Carbonyl compounds", "Carboxylic acid salts", "Carboxylic acids", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Imidazolethiones", "Imidazolyl carboxylic acids and derivatives", "L-alpha-amino acids", "Monocarboxylic acids and derivatives", "Organic oxides", "Organic salts", "Organopnictogen compounds", "Tetraalkylammonium salts", "Thioureas"]
External Descriptor Annotations
["L-histidine derivative", "amino-acid betaine"]
Substituent Names
["Alpha-amino acid", "Amine", "Aralkylamine", "Aromatic heteromonocyclic compound", "Azacycle", "Azole", "Carbonyl group", "Carboxylic acid", "Carboxylic acid salt", "Heteroaromatic compound", "Histidine or derivatives", "Hydrocarbon derivative", "Imidazole", "Imidazole-2-thione", "Imidazolyl carboxylic acid derivative", "L-alpha-amino acid", "Monocarboxylic acid or derivatives", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organic salt", "Organoheterocyclic compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Organosulfur compound", "Quaternary ammonium salt", "Tetraalkylammonium salt", "Thiourea"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(28.01817382,1.499158974);(43.97152142,1.143372239);(43.98927962,2.347412941);(44.97934602,2.347628066);(57.05729682,0.943218057);(58.06512142,2.278235065);(58.98241922,1.774489122);(59.07294602,2.741306972);(59.99024382,0.8606557246);(60.08077062,3.376259116);(71.99024382,0.9594471441);(86.09641982,1.047831447);(99.00114162,0.8971546701);(111.0011416,4.278343518);(112.0089662,2.73308495);(113.0167908,2.359245791);(125.1073176,1.058743686);(126.0246154,1.203738238);(127.03244,1.610802553);(157.0793876,0.9044003927);(170.0144436,1.008217665);(170.0746362,2.467176251);(181.0668116,1.055069882);(182.0746362,0.9934854584);(183.0824608,1.964249914);(184.0902854,2.801201592);(185.09811,10.45062154);(186.1006123,1.157136152);(212.0851995,1.080631598);(228.0801136,2.270378886);(229.0879382,1.53668366)
Predicted GC-MSGC-MSEiNot AvailableView Spectrum(28.01817382,1.499158974);(43.97152142,1.143372239);(43.98927962,2.347412941);(44.97934602,2.347628066);(57.05729682,0.943218057);(58.06512142,2.278235065);(58.98241922,1.774489122);(59.07294602,2.741306972);(59.99024382,0.8606557246);(60.08077062,3.376259116);(71.99024382,0.9594471441);(86.09641982,1.047831447);(99.00114162,0.8971546701);(111.0011416,4.278343518);(112.0089662,2.73308495);(113.0167908,2.359245791);(125.1073176,1.058743686);(126.0246154,1.203738238);(127.03244,1.610802553);(157.0793876,0.9044003927);(170.0144436,1.008217665);(170.0746362,2.467176251);(181.0668116,1.055069882);(182.0746362,0.9934854584);(183.0824608,1.964249914);(184.0902854,2.801201592);(185.09811,10.45062154);(186.1006123,1.157136152);(212.0851995,1.080631598);(228.0801136,2.270378886);(229.0879382,1.53668366)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(41.03825,11.66);(42.03327,6.9);(43.04247,2.15);(45.05737,1.26);(54.03388,1.51);(56.0505,3.97);(58.06458,2.53);(58.99472,4.77);(60.08208,46.19);(67.04364,19.16);(68.05138,50.78);(69.05803,64.89);(82.05183,1.01);(83.06236,5.75);(85.01279,1.41);(86.0061,6.6);(93.04415,5.96);(94.05304,9.74);(95.06063,2.17);(100.0236,32.06);(114.0231,1.38);(115.0359,2.45);(125.0199,1.03);(127.0362,100.0);(129.0137,1.38);(136.0874,1.1);(143.0276,6.34)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(41.03825,40.39);(42.03327,13.51);(43.04247,11.22);(44.04989,4.47);(45.05737,5.88);(54.03388,6.52);(55.03117,1.07);(56.0505,16.54);(58.06458,8.09);(58.99472,7.42);(60.08208,51.68);(66.035,5.7);(67.04364,51.41);(68.05138,77.84);(69.05803,100.0);(71.99038,2.09);(73.00793,1.13);(74.00887,2.1);(82.05183,2.14);(83.06236,12.86);(85.01279,1.28);(86.0061,5.03);(93.04749,8.96);(94.05304,23.6);(95.064,3.37);(100.0236,25.64);(113.0111,1.22);(114.0267,7.66);(115.0359,4.95);(125.016,1.38);(127.0362,38.69);(129.0137,1.28);(136.0834,1.43);(143.0317,4.71)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(42.03327,1.48);(60.08208,25.85);(67.04364,2.13);(68.05138,7.2);(69.05803,10.67);(83.06236,1.03);(86.0061,2.61);(100.0236,8.21);(127.0362,100.0);(143.0276,2.67);(186.1094,5.76)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(60.08208,42.04);(68.05138,1.95);(69.05803,1.75);(86.0061,1.25);(100.0236,2.07);(127.0362,87.14);(143.0276,1.07);(171.0246,2.08);(186.1094,100.0);(230.0993,49.69)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(60.07912,9.01);(68.04825,2.85);(100.02122,4.74);(115.03317,1.9);(127.03365,100.0);(143.02953,1.9);(186.10284,14.88);(230.09592,1.9)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(58.9952,1.32);(60.0809,27.45);(67.0418,3.33);(68.0496,9.96);(69.0574,14.23);(83.0604,1.53);(86.0059,3.44);(94.0526,1.89);(100.0216,10.38);(127.0325,100.0);(143.0275,2.12);(186.1061,30.32);(230.096,7.9)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(58.06475,52.1);(59.07236,24.2);(60.08014,28.0);(82.05253,6.7);(98.05983,5.9);(181.98688,5.9);(186.10626,100.0);(188.10066,6.7);(230.09602,40.9)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(61.04706,3.6);(113.96363,38.0);(186.1062,26.2);(187.12628,70.0);(188.09482,5.1);(230.09595,100.0)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(58.06475,1.49);(59.07247,2.57);(60.08013,20.48);(69.05663,1.15);(126.0238,1.0);(127.03253,48.37);(128.03537,2.79);(129.02791,1.91);(165.00951,2.98);(186.10599,100.0);(187.10979,8.59);(188.10283,3.42);(208.08792,2.55);(230.09602,39.72);(231.0992,4.06);(232.09406,1.69);(252.07822,13.78);(253.08142,1.64);(268.0517,7.88);(459.18387,3.25)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(41.03784,9.0);(56.04883,2.15);(58.06475,4.89);(60.08013,44.61);(61.08364,1.26);(67.04068,12.29);(68.04894,47.14);(69.05663,64.29);(70.06479,2.36);(83.05955,5.39);(86.00592,5.53);(93.0434,2.9);(95.06,1.04);(100.02126,21.33);(102.01357,1.09);(127.03253,100.0);(128.03537,5.79);(129.02791,4.19);(143.02794,3.31);(149.02271,2.66);(165.00951,10.05);(178.04214,4.43);(180.98331,1.3);(186.10599,40.61);(187.10979,3.57);(188.10283,1.52);(193.00546,2.57);(208.08792,10.08);(209.09019,1.11);(214.9855,2.09);(230.09602,16.66);(231.0992,1.93);(252.07822,64.51);(253.08142,6.27);(254.07463,2.8);(268.0517,13.35);(269.05423,1.71);(270.04974,1.6)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(127.03253,5.93);(186.10599,28.24);(187.10979,2.53);(188.10283,1.01);(230.09602,100.0);(231.0992,9.45);(232.09406,4.11);(252.07822,14.67);(253.08142,1.49);(268.0517,8.78);(459.18387,6.25);(460.18616,1.36)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(41.03763,22.5);(42.0331,100.0);(43.04042,14.7);(54.03316,10.2);(56.0489,20.3);(58.06477,75.3);(59.07206,9.0);(60.08004,10.6);(61.03922,3.3);(68.04909,12.6);(70.06374,5.8);(79.05347,4.7);(81.04456,2.6);(82.05212,3.0);(83.0595,4.0);(95.05922,2.1);(119.08488,1.5)
LC-MS/MSLC-ESI-QTOFPositivehighView Spectrum(54.0342,0.14514515);(56.0498,0.1951952);(60.0811,0.51051051);(67.0421,0.67367367);(68.0499,0.82382382);(69.0578,1.0);(94.0531,0.26826827)
LC-MS/MSLC-ESI-QTOFPositivemediumView Spectrum(60.081,0.28328328);(127.0324,1.0);(186.1061,0.53653654)
LC-MS/MSLC-ESI-QTOFPositivehighView Spectrum(60.0812,0.53653654);(67.0421,0.34334334);(68.05,0.7017017);(69.0578,1.0);(100.0221,0.37137137);(127.0329,0.90790791)
LC-MS/MSLC-ESI-QTOFPositivehighView Spectrum(54.0342,0.37937938);(56.0498,0.32732733);(58.0655,0.33933934);(59.9907,0.25925926);(60.0811,0.48948949);(67.0421,1.0);(68.05,0.77777778);(69.0578,0.72572573)
LC-MS/MSLC-ESI-QTOFPositivemediumView Spectrum(60.0811,0.21221221);(68.05,0.1001001);(69.0577,0.15515516);(100.022,0.1041041);(127.0325,1.0)
LC-MS/MSLC-ESI-QFTPositivehighView Spectrum(58.9952,0.01301301);(60.0809,0.27427427);(67.0418,0.03303303);(68.0496,0.0990991);(69.0574,0.14214214);(83.0604,0.01501502);(86.0059,0.03403403);(94.0526,0.01801802);(100.0216,0.1031031);(127.0325,1.0);(143.0275,0.02102102);(186.1061,0.3023023);(230.096,0.07807808)
LC-MS/MSLC-ESI-QTOFPositivelowView Spectrum(58.06475,0.521);(59.07236,0.242);(60.08014,0.28);(82.05253,0.067);(98.05983,0.059);(181.98688,0.059);(186.10626,1.0);(188.10066,0.067);(230.09602,0.409)
LC-MS/MSLC-ESI-QTOFPositivemediumView Spectrum(54.03316,0.102);(56.0489,0.203);(58.06477,0.753);(59.07206,0.09);(60.08004,0.106);(61.03922,0.033);(68.04909,0.126);(70.06374,0.058);(79.05347,0.047);(81.04456,0.026);(82.05212,0.03);(83.0595,0.04);(95.05922,0.021);(119.08488,0.015)
LC-MS/MSLC-ESI-QTOFPositivelowView Spectrum(58.06475,0.0148984);(59.07247,0.02570085);(60.08013,0.204812);(69.05663,0.01146656);(126.0238,0.01001116);(127.03253,0.48366386);(128.03537,0.02787688);(129.02791,0.01913213);(164.98824,0.02133642);(165.00951,0.02977738);(186.10599,1.0);(187.10979,0.08587734);(188.10283,0.03419656);(208.08792,0.02546947);(230.09602,0.39715244);(231.0992,0.0405604);(232.09406,0.01689958)
LC-MS/MSLC-ESI-QTOFPositivemediumView Spectrum(56.04883,0.02153878);(58.06475,0.04889534);(60.08013,0.44605199);(61.08364,0.01258257);(67.04068,0.12285478);(68.04894,0.47141059);(69.05663,0.64290375);(70.06479,0.02361759);(83.05955,0.05393068);(86.00592,0.0552617);(93.0434,0.0289994);(95.06,0.0103825);(100.02126,0.21334942);(102.01357,0.01092241);(127.03253,1.0);(128.03537,0.05785444);(129.02791,0.04187936);(143.02794,0.03305597);(149.02271,0.02661743);(164.98824,0.02889835);(165.00951,0.10053934);(178.04214,0.04431041);(180.98331,0.01298101);(186.10599,0.4061475);(187.10979,0.03568335);(188.10283,0.01520996);(193.00546,0.02568774);(208.08792,0.10077609);(209.09019,0.01110142);(214.9855,0.02088915);(230.09602,0.16659641);(231.0992,0.01932427)
LC-MS/MSLC-ESI-QTOFPositivelowView Spectrum(60.08208,0.42035524);(68.05138,0.01951125);(69.05803,0.01747789);(86.0061,0.01246552);(100.0236,0.02066996);(127.0362,0.87139771);(143.0276,0.01067138);(171.0246,0.02083442);(186.1094,1.0);(230.0993,0.4969238)
LC-MS/MSLC-ESI-QTOFPositivemediumView Spectrum(60.08208,0.2585046);(67.04364,0.02132855);(68.05138,0.07202068);(69.05803,0.10669325);(83.06236,0.01026884);(86.0061,0.02609277);(100.0236,0.08210021);(127.0362,1.0);(143.0276,0.02674062);(186.1094,0.05762075)
LC-MS/MSLC-ESI-QTOFPositivemediumView Spectrum(54.03388,0.01510701);(56.0505,0.03972808);(58.06458,0.02527877);(58.99472,0.04773596);(59.99109,0.03268417);(60.08208,0.46187098);(67.04364,0.19162161);(68.05138,0.50775433);(69.05803,0.64886861);(82.05183,0.01009143);(83.06236,0.05747594);(85.01279,0.01412297);(86.0061,0.06599089);(93.04415,0.05962978);(94.05304,0.09737974);(95.06063,0.02170912);(100.0236,0.32063621);(114.0231,0.01380166);(115.0359,0.02448049);(125.0199,0.01026715);(127.0362,1.0);(129.0137,0.01384684);(136.0874,0.01104534);(143.0276,0.06338018)
LC-MS/MSLC-ESI-QTOFPositivehighView Spectrum(54.03388,0.06523474);(55.03117,0.01074349);(56.0505,0.16544489);(58.06458,0.0808572);(58.99472,0.07422702);(59.99109,0.1120288);(60.08208,0.51681165);(66.035,0.05700811);(67.04364,0.5141156);(68.05138,0.77838595);(69.05803,1.0);(71.99038,0.02085981);(73.00793,0.01128922);(74.00887,0.02100642);(82.05183,0.0213811);(83.06236,0.12863682);(85.01279,0.01277164);(86.0061,0.05031277);(93.04749,0.08959698);(94.05304,0.23603916);(95.064,0.03368032);(100.0236,0.25636139);(113.0111,0.01221777);(114.0267,0.076638);(115.0359,0.04949826);(125.016,0.01378164);(127.0362,0.3868716);(129.0137,0.01278793);(136.0834,0.01425406);(143.0317,0.0471443)
LC-MS/MSLC-ESI-QPositivehighView Spectrum(58.995,0.013);(60.081,0.275);(67.042,0.033);(68.05,0.1);(69.057,0.142);(83.06,0.015);(86.006,0.034);(94.053,0.019);(100.022,0.104);(127.032,1.0);(143.028,0.021);(186.106,0.303);(230.096,0.079)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(113.0167956,2.568034333);(154.086255,3.951545752);(171.1128041,3.890575076);(184.0902949,3.131278108);(212.0852095,10.35320888);(230.0957742,62.93575983)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(60.08077574,2.203377444);(113.0167956,7.357833864);(154.086255,8.816500851);(171.1128041,6.868374527);(182.0746448,3.066948522);(184.0902949,10.44116097);(186.1059449,6.684779949);(196.1080531,3.290795745);(212.0852095,8.077192236);(213.0692251,3.400454468);(230.0957742,21.49269749)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(15.02292652,1.364109801);(40.01817548,5.561963758);(42.03382555,2.18882637);(50.00252542,1.382142744);(52.01817548,2.306678659);(54.03382555,10.11635983);(55.02907452,1.247636623);(59.99024648,1.030886752);(67.02907452,1.752644526);(69.04472458,7.869222164);(110.0964258,6.207017623);(113.0167956,2.169924475);(113.1073248,1.339790435);(125.1073248,4.022076885);(130.086255,3.170028231);(140.1182239,3.729715305);(142.086255,2.757021224);(154.086255,7.683856756);(155.081504,1.153761121);(157.0971541,2.50763272);(167.081504,2.567635548);(169.0971541,5.101734634);(171.1128041,1.543491518);(182.092403,0.9849192641);(186.1237032,0.9613595964)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(32.98044461,1.854477309);(75.00224268,1.10727385);(137.035651,2.251268175);(169.007722,8.198249448);(171.023372,5.793006872);(228.0812213,76.59658624)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(32.98044461,9.09619396);(44.98044461,2.706283592);(57.97569358,3.25660746);(96.98659261,2.224574739);(99.00224268,3.580358283);(125.0178927,2.385178254);(169.007722,15.74436821);(171.023372,6.327584057);(228.0812213,35.83308561)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(26.00362258,1.553823514);(32.98044461,11.95360648);(44.98044461,1.854237161);(57.97569358,66.39901327);(59.99134364,1.915175485);(125.0178927,1.602978861)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(184.09029,57.0);(184.09029,57.0);(184.09029,57.0);(184.09029,57.0);(186.10594,46.04);(186.10594,46.04);(186.10594,46.04);(186.10594,46.04);(186.10594,46.04);(230.09577,100.0);(230.09577,100.0);(230.09577,100.0);(230.09577,100.0);(230.09577,100.0);(230.09577,100.0)
Predicted LC-MS/MSNot AvailablePositivemediumView Spectrum(60.08078,12.51);(101.0168,12.14);(101.0168,12.14);(101.0168,12.14);(101.0168,12.14);(113.0168,9.42);(113.0168,9.42);(113.0168,9.42);(113.0168,9.42);(113.0168,9.42);(125.0168,48.88);(127.03245,64.99);(153.01171,14.63);(171.02227,100.0);(171.02227,100.0);(171.02227,100.0);(171.02227,100.0);(171.02227,100.0);(171.02227,100.0);(184.09029,23.1);(184.09029,23.1);(184.09029,23.1);(184.09029,23.1);(186.10594,16.05);(186.10594,16.05);(186.10594,16.05);(186.10594,16.05);(186.10594,16.05);(230.09577,31.17);(230.09577,31.17);(230.09577,31.17);(230.09577,31.17);(230.09577,31.17);(230.09577,31.17)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(54.03383,4.95);(58.06513,17.4);(60.08078,61.52);(71.99025,6.41);(73.02841,15.23);(75.04406,5.81);(86.09643,21.0);(95.01276,6.68);(99.00115,12.86);(99.00115,12.86);(101.0168,14.01);(101.0168,14.01);(101.0168,14.01);(101.0168,14.01);(110.02365,5.5);(110.02365,5.5);(111.00115,8.04);(111.00115,8.04);(112.0393,6.56);(112.0393,6.56);(113.0168,6.35);(113.0168,6.35);(113.0168,6.35);(113.0168,6.35);(113.0168,6.35);(123.00115,18.02);(125.0168,47.31);(127.03245,100.0);(127.0502,5.82);(129.0481,6.21);(154.08626,7.59);(155.02736,4.92);(169.00662,12.18);(169.00662,12.18);(171.02227,6.83);(171.02227,6.83);(171.02227,6.83);(171.02227,6.83);(171.02227,6.83);(171.02227,6.83)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(228.08122,100.0)
Predicted LC-MS/MSNot AvailableNegativemediumView Spectrum(96.98659,27.68);(96.98659,27.68);(99.00224,34.35);(99.00224,34.35);(99.00224,34.35);(99.00224,34.35);(169.00772,30.11);(169.00772,30.11);(169.00772,30.11);(169.00772,30.11);(169.00772,30.11);(228.08122,100.0)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(44.9982,19.52);(57.97569,45.66);(96.98659,41.31);(96.98659,41.31);(99.00224,25.36);(99.00224,25.36);(99.00224,25.36);(99.00224,25.36);(111.00224,19.42);(111.00224,19.42);(111.00224,19.42);(111.00224,19.42);(123.00224,12.72);(125.01789,100.0);(169.00772,34.22);(169.00772,34.22);(169.00772,34.22);(169.00772,34.22);(169.00772,34.22)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

No food source information available of its precursor(s)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

No metabolism information available

Inter-Individual Variations in Metabolism

No data on inter-individual variations available

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