precursor

Showing entry for Cafestol

Identification

PhytoHub ID
PHUB000006
Name
Cafestol
Systematic Name
Not Available
Synonyms
  • (−)-cafestol
  • Cafesterol
CAS Number
469-83-0
Average Mass
316.441
Monoisotopic Mass
316.203844762
Chemical Formula
C20H28O3
IUPAC Name
(1S,4S,12S,13R,16S,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6-dien-17-ol
InChI Key
DNJVYWXIDISQRD-JTSSGKSMSA-N
InChI Identifier
InChI=1S/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15+,17-,18+,19-,20-/m0/s1
SMILES
C[C@@]12CCC3=C(C=CO3)[C@H]1CC[C@@]13C[C@H](CC[C@@H]21)[C@@](O)(CO)C3
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.80e-02 g/l
LogS (ALOGPS)
-4.24
LogP (ALOGPS)
3.04
Hydrogen Acceptors
2
Hydrogen Donors
2
Rotatable Bond Count
1
Polar Surface Area
53.60000000000001
Refractivity
88.55009999999999
Polarizability
75.87981266270646
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-2.7454146697920976
pKa (strongest acidic)
13.685426593369503
Number of Rings
5
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Terpenoids
Class
Diterpenoids
Sub-class
Not Available

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Naphthofurans
Super-class
Organoheterocyclic compounds
Sub-class
Not Available
Direct Parent Name
Naphthofurans
Alternative Parent Names
["1,2-diols", "Benzofurans", "Cyclic alcohols and derivatives", "Furans", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Oxacyclic compounds", "Primary alcohols", "Tertiary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["1,2-diol", "Alcohol", "Aromatic heteropolycyclic compound", "Benzofuran", "Cyclic alcohol", "Furan", "Heteroaromatic compound", "Hydrocarbon derivative", "Naphthofuran", "Organic oxygen compound", "Organooxygen compound", "Oxacycle", "Primary alcohol", "Tertiary alcohol"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(95.04968984,0.5464447384);(133.0653399,0.555197696);(135.08099,0.8683761701);(147.08099,0.5723777155);(149.09664,1.209602413);(153.0915547,0.4827129993);(155.1072047,0.7205741325);(161.09664,0.5523905922);(163.1122901,0.8596147822);(167.1072047,0.513112329);(169.1228548,1.04807906);(181.1228548,0.4862949983);(183.1385048,0.7194180883);(221.1541549,0.6880777832);(223.169805,1.118477276);(235.169805,0.3436906129);(241.1592403,0.5705621367);(245.1905404,0.3314216001);(247.169805,0.3875941496);(249.185455,0.8454760212);(255.1748904,0.6685214573);(259.2061905,0.453508164);(267.1748904,0.6830687187);(281.1905404,4.721963275);(285.185455,1.706301807);(287.2011051,0.8918701226);(289.1803697,0.6381709768);(299.2011051,16.5150077);(301.1803697,0.7398123242);(301.1803697,0.4197091983);(317.2116698,59.14257096)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(93.03403978,1.18840231);(95.04968984,3.113350964);(133.0653399,1.818947437);(135.08099,2.502409386);(147.08099,1.993201433);(149.09664,2.508223098);(155.1072047,1.323242046);(161.09664,1.719206025);(163.1122901,2.400720406);(167.1072047,1.245363549);(169.1228548,1.686927388);(183.1385048,1.313973118);(203.1435902,1.571933717);(205.1592403,1.675881375);(221.1541549,1.798498298);(223.169805,3.718467349);(229.1592403,2.122836567);(231.1748904,3.157571286);(241.1592403,2.201674947);(249.185455,4.347207311);(255.1748904,1.979235472);(267.1748904,1.162835406);(281.1905404,10.31893894);(285.185455,1.989203432);(287.2011051,1.129035216);(289.1803697,1.675462846);(291.1960197,1.24118585);(299.2011051,16.89027243);(301.1803697,1.8482744);(301.1803697,1.815402506);(317.2116698,16.54211549)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(41.03912516,3.907109036);(43.05477522,4.073895485);(51.0234751,3.025761895);(53.03912516,3.799283716);(57.07042529,2.866970899);(67.05477522,2.430328292);(79.05477522,5.250077233);(93.07042529,6.282130805);(105.0704253,2.351342312);(107.0860754,2.562050572);(133.0653399,2.214098254);(137.09664,3.382674011);(145.1017254,2.312198234);(147.1173755,3.874912973);(151.0759046,2.361568004);(151.1122901,2.669363269);(165.1279402,3.215196555);(173.1330255,9.278337848);(175.1486756,2.175866444);(187.1486756,2.031581208);(205.1592403,2.489174446);(211.1486756,2.053971542);(227.1435902,2.357006442);(229.1592403,4.504054995);(231.1748904,2.830042297);(267.1748904,2.204249647);(269.1905404,2.68467894);(281.1905404,2.075140531);(283.169805,2.077424999);(289.1803697,2.880515907);(301.1803697,3.77899321)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(15.0234751,0.3293872827);(17.00273965,0.355271448);(25.00782503,0.0710093507);(29.00273965,0.1338959813);(31.01838972,0.1515101833);(41.00273965,0.2054114111);(43.01838972,0.1005666125);(73.0289544,0.0543493329);(93.03403978,0.0785698749);(133.0653399,0.154521383);(147.08099,0.0668533683);(153.0915547,0.1443746136);(161.09664,0.154521383);(167.1072047,0.0624633887);(181.1228548,0.1443746136);(221.1541549,0.0697035469);(241.1592403,0.0640213509);(255.1748904,0.1347000291);(257.1905404,0.0925643057);(265.1592403,0.400301495);(267.1748904,4.304154862);(269.1541549,0.0563730841);(273.185455,0.0895847012);(279.1748904,1.428701348);(283.169805,1.880114412);(285.185455,9.606288387);(287.1647196,0.4462925485);(289.1803697,0.0985287376);(297.185455,9.549130434);(299.1647196,0.8057298672);(315.1960197,68.76673066)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(17.00273965,0.5199587185);(41.00273965,0.4810592405);(43.01838972,0.2596158777);(93.03403978,0.1287769722);(133.0653399,0.2152135508);(153.0915547,0.1638022859);(161.09664,0.2152135508);(181.1228548,0.1638022859);(221.1541549,0.1169330486);(241.1592403,0.3090132788);(253.1592403,0.2703415405);(255.1385048,0.1874224242);(255.1748904,0.5080731791);(257.1541549,0.2185303502);(257.1541549,0.1408130003);(257.1905404,0.2588302706);(259.169805,0.2479676887);(265.1592403,1.458032912);(267.1748904,14.37367054);(269.1541549,0.2158063351);(273.185455,0.1508752884);(279.1748904,1.02453639);(283.169805,10.10423772);(285.1490695,0.7372565239);(285.185455,20.39981158);(287.1647196,0.8375202666);(289.1803697,0.2313508411);(289.1803697,0.4710595659);(297.185455,11.32822249);(299.1647196,1.815643481);(315.1960197,32.44660881)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(67.01838972,1.277735748);(133.0653399,0.6687226571);(161.09664,0.6687226571);(239.1435902,1.179069618);(241.1592403,1.20623801);(243.1748904,0.647459321);(251.1435902,2.565884018);(253.1228548,1.578545596);(253.1592403,14.11539384);(255.1385048,5.194084122);(255.1748904,10.84437988);(257.1541549,2.969168591);(257.1541549,3.135850451);(257.1905404,0.6698092678);(259.169805,2.554265556);(265.1592403,1.380701425);(267.1385048,1.326933043);(267.1385048,1.438641913);(267.1748904,7.301979376);(269.1541549,3.596421093);(269.1541549,3.389524056);(281.1541549,0.6844916311);(283.169805,6.534068286);(285.1490695,2.595282806);(285.185455,10.85160133);(287.1647196,1.908123477);(289.1803697,1.1425476);(297.185455,1.735035083);(299.1647196,3.686707409);(299.1647196,1.945209074);(315.1960197,1.207403063)

Food Sources

NameGroup
Arabica coffeeCoffee and coffee products PublicationsShow
Arabica coffee oilCoffee and coffee products PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
Robusta coffeeCoffee and coffee products PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Cafestol CafestolhumanurineunchangedNot AvailableNot Available1-5%C20H28O3316.203844762 Detailed Intervention Studies Publications
Cafestol Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)mousebileunknownNot AvailableNot AvailableNot AvailableC30H45N3O11S655.277480455 Publications
Cafestol Cafestol (2-hydroxy-)mousebileunknownNot AvailableNot AvailableNot AvailableC20H28O4332.198759382 Publications
Cafestol Cafestol (2-hydroxy-,3,4-epoxide)mousebileunknownNot AvailableNot AvailableNot AvailableC20H28O5348.193674002 Publications
Cafestol Cafestol glucuronidehuman mousebile, blood, urinehost metabolismNot AvailableNot AvailableNot AvailableC26H36O9492.5678392 Publications
Cafestol Cafestol sulfatehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC20H28O6S396.5042844 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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