metabolite

Showing entry for Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)

Identification

PhytoHub ID
PHUB000913
Name
Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
655.76
Monoisotopic Mass
655.277480455
Chemical Formula
C30H45N3O11S
IUPAC Name
2-amino-4-({1-[(carboxymethyl)carbamoyl]-2-{[(1S,12S,17R)-6,10,17-trihydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-5(9)-en-7-yl]sulfanyl}ethyl}carbamoyl)butanoic acid
InChI Key
CWHSNVYWYFOEQJ-XOOUWMDMSA-N
InChI Identifier
InChI=1S/C30H45N3O11S/c1-28-9-18(35)24-22(15(28)6-7-29-8-14(2-4-19(28)29)30(43,12-29)13-34)23(39)27(44-24)45-11-17(25(40)32-10-21(37)38)33-20(36)5-3-16(31)26(41)42/h14-19,23,27,34-35,39,43H,2-13,31H2,1H3,(H,32,40)(H,33,36)(H,37,38)(H,41,42)/t14?,15?,16?,17?,18?,19?,23?,27?,28-,29+,30+/m1/s1
SMILES
C[C@@]12CC(O)C3=C(C(O)C(O3)SCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O)C1CC[C@@]13CC(CCC21)[C@@](O)(CO)C3
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
4.18e-01 g/l
LogS (ALOGPS)
-3.20
LogP (ALOGPS)
-3.08
Hydrogen Acceptors
12
Hydrogen Donors
9
Rotatable Bond Count
12
Polar Surface Area
248.96999999999994
Refractivity
159.88000000000005
Polarizability
68.34345255860144
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
9.311345895281136
pKa (strongest acidic)
1.781959152250963
Number of Rings
5
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

Taxonomy as Metabolite

Family
Terpenoid metabolites
Class
Diterpenoid metabolites
Sub-class
Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
CafestolTerpenoidsDiterpenoidsNot AvailableShow Food Phytochemical

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
Oligopeptides
Alternative Parent Names
["Alpha amino acid amides", "Alpha amino acids", "Amino acids", "Carbonyl compounds", "Carboxylic acids", "Cyclic alcohols and derivatives", "Cysteine and derivatives", "Dicarboxylic acids and derivatives", "Dihydrofurans", "Diterpenoids", "Gamma-glutamyl peptides", "Glutamine and derivatives", "Heterocyclic fatty acids", "Hydrocarbon derivatives", "Hydroxy fatty acids", "Monoalkylamines", "Monothioacetals", "N-acyl amines", "N-acyl-alpha amino acids", "Naphthofurans", "Organic oxides", "Organopnictogen compounds", "Oxacyclic compounds", "Oxasteroids and derivatives", "Polyols", "Primary alcohols", "Secondary alcohols", "Secondary carboxylic acid amides", "Sulfenyl compounds", "Tertiary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["17-oxasteroid", "Alcohol", "Aliphatic heteropolycyclic compound", "Alpha-amino acid", "Alpha-amino acid amide", "Alpha-amino acid or derivatives", "Alpha-oligopeptide", "Amine", "Amino acid", "Amino acid or derivatives", "Carbonyl group", "Carboxamide group", "Carboxylic acid", "Cyclic alcohol", "Cysteine or derivatives", "Dicarboxylic acid or derivatives", "Dihydrofuran", "Diterpenoid", "Fatty acyl", "Fatty amide", "Gamma-glutamyl alpha peptide", "Glutamine or derivatives", "Heterocyclic fatty acid", "Hydrocarbon derivative", "Hydroxy fatty acid", "Monothioacetal", "N-acyl-alpha amino acid or derivatives", "N-acyl-alpha-amino acid", "N-acyl-amine", "N-substituted-alpha-amino acid", "Naphthofuran", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Organosulfur compound", "Oxacycle", "Polyol", "Primary alcohol", "Primary aliphatic amine", "Primary amine", "Secondary alcohol", "Secondary carboxylic acid amide", "Steroid", "Sulfenyl compound", "Tertiary alcohol"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(74.02420337,9.433745151);(76.03985343,2.411586046);(102.0555035,1.002188035);(143.0456671,1.022660444);(177.0333881,2.419056283);(205.0646883,1.370765077);(228.0984309,3.268444682);(233.0596029,1.006011063);(260.0705019,4.985602716);(262.086152,5.155713958);(264.1018021,2.100058297);(274.1039102,5.982538323);(290.0810666,4.274432038);(291.0650822,2.502817429);(306.0759812,2.13951322);(307.1909343,2.111637049);(308.0916313,7.608708541);(316.1542316,1.062057362);(319.1909343,1.993304554);(335.185849,3.537345223);(337.201499,6.24189901);(339.2171491,0.9887206882);(349.201499,2.894092545);(422.2001191,1.935303976);(525.2270621,4.98829157);(553.2583623,1.27844884);(610.279826,4.79238609);(638.2747406,4.634976634);(638.2747406,1.140659759);(639.2587562,1.398335962);(656.2853053,4.318699434)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(56.05002419,1.618708094);(74.02420337,30.49312229);(76.03985343,1.262741391);(86.06058888,2.057856729);(102.0555035,1.286627686);(130.0504181,1.284153813);(205.0646883,2.618556516);(228.0984309,1.518377165);(260.0705019,1.275611612);(262.086152,3.227772746);(331.1909343,1.659798095);(331.1909343,1.596524638);(349.201499,6.901121191);(365.1786554,1.947759592);(381.17357,1.700961069);(383.1892201,2.146072358);(422.2001191,3.684135771);(424.2157692,2.489498518);(495.2164975,1.282230238);(507.252883,4.268799402);(525.2270621,5.46087978);(535.2477976,2.055058734);(537.2634477,1.771069338);(553.2583623,4.20637709);(564.2743467,1.552516072);(580.2692613,1.259237724);(592.2692613,1.864335827);(592.2692613,1.246965452);(593.2532769,1.152928972);(610.279826,3.642500666);(638.2747406,1.467701431)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(56.05002419,3.384051003);(74.02420337,20.54509397);(76.03985343,2.043653796);(102.0555035,1.45156155);(151.0759046,1.8959602);(153.0915547,1.816335141);(171.0769672,1.798148948);(179.1072047,1.8959602);(181.1228548,1.816335141);(203.0490382,2.158942844);(205.0646883,2.721689401);(219.1385048,2.266585903);(221.1541549,4.04735069);(260.0705019,2.831839009);(261.1490695,2.238177631);(263.1647196,1.567668919);(265.1803697,2.615832433);(275.1647196,2.637080467);(277.1803697,2.322875087);(279.1960197,1.863190946);(289.1803697,2.546395652);(305.1752843,2.190411717);(307.1909343,1.493877907);(315.1596342,2.336069838);(317.1752843,2.383368751);(319.1909343,7.817945771);(321.2065844,5.885143182);(323.2222345,1.533184679);(333.1701989,1.591555369);(335.185849,3.93316863);(337.201499,4.370545228)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(44.97989603,3.118756882);(130.0504181,2.987180119);(145.0613171,1.389708814);(175.0177381,1.139756577);(205.0646883,0.8179493355);(258.0726101,0.9122226795);(260.0705019,0.8895412292);(260.0882602,1.319332873);(262.086152,3.599021124);(272.0705019,0.9919269977);(272.0882602,6.614573215);(274.1039102,1.004405868);(288.0654165,7.829160594);(289.0494321,5.18897607);(300.0654165,1.193787187);(306.0759812,22.5674164);(318.0759812,3.505483765);(320.0916313,1.13475608);(347.185849,4.696669428);(363.1630053,1.084991222);(381.17357,2.026518846);(525.2270621,0.8290188093);(553.2583623,1.157180472);(581.2532769,1.135629299);(592.2692613,1.369933858);(606.2485259,1.333759488);(608.2641759,0.9179938193);(610.279826,2.884718559);(624.2590905,1.620365255);(636.2590905,4.489761919);(654.2696552,10.24950321)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(74.02420337,3.28317531);(128.0347681,4.273588442);(130.0504181,2.768732763);(143.0456671,3.303061087);(145.0613171,2.203023358);(160.0068391,2.112586238);(175.0177381,2.68990901);(228.0984309,3.54932441);(230.114081,2.079629601);(256.0933455,3.14713487);(258.1089956,1.444134124);(260.0705019,1.924303611);(262.086152,2.777697235);(270.0726101,1.766144761);(272.0882602,7.226549979);(274.1039102,2.025767519);(288.0654165,5.046660046);(289.0494321,1.659986786);(306.0759812,11.8698962);(315.1596342,1.617177536);(317.1752843,3.366473198);(347.185849,9.923539296);(351.1630053,1.773608748);(381.17357,2.025190819);(580.2692613,1.831461406);(606.2485259,2.681376611);(608.2641759,1.578718579);(610.279826,1.524142265);(624.2590905,2.176475186);(636.2590905,4.057839523);(654.2696552,2.292691484)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,2.104045692);(41.99798862,3.757325985);(72.0085533,1.755564765);(74.02420337,1.435675917);(74.99046072,3.590494376);(100.0034679,1.935486483);(130.0504181,1.46048137);(143.0456671,3.148748083);(145.0613171,3.988634608);(175.0177381,2.183667084);(217.0283028,1.546236582);(272.0882602,3.504159226);(273.1490695,1.460286205);(275.1647196,3.549139946);(287.1647196,1.702729934);(289.1803697,2.766459611);(291.1960197,1.938739255);(301.1439842,1.309049515);(303.1596342,1.287885709);(305.1752843,4.414445325);(306.0759812,1.884266358);(315.1596342,5.484216853);(317.1752843,12.53134523);(319.1909343,2.521837569);(323.2222345,1.213198025);(329.1752843,1.62495866);(347.185849,16.26481284);(349.1473553,2.403845586);(351.1630053,3.133199163);(363.1630053,1.6398315);(381.17357,2.459232543)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
CafestolArabica coffeeCoffee and coffee products PublicationsShow
CafestolArabica coffee oilCoffee and coffee products PublicationsShow
CafestolCoffeeCoffee and coffee products PublicationsShow
CafestolRobusta coffeeCoffee and coffee products PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Cafestol Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)mousebileunknownNot AvailableNot AvailableNot AvailableC30H45N3O11S655.277480455 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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