PhytoHub: Showing entry for Kahweol

Kahweol

Identification

PhytoHub ID

PHUB000010

Name

Kahweol

Systematic Name

Not Available

Synonyms

Not Available

CAS Number

6894-43-5

Average Mass

314.425

Monoisotopic Mass

314.188194697

Chemical Formula

C₂₀H₂₆O₃

IUPAC Name

(1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6,10-trien-17-ol

InChI Key

JEKMKNDURXDJAD-HWUKTEKMSA-N

InChI Identifier

InChI=1S/C20H26O3/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/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1

SMILES

C[C@@]12C=CC3=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): 2.01e-02 g/l
LogS (ALOGPS): -4.19
LogP (ALOGPS): 2.97
Hydrogen Acceptors: 2
Hydrogen Donors: 2
Rotatable Bond Count: 1
Polar Surface Area: 53.60000000000001
Refractivity: 89.51269999999998
Polarizability: 35.49468732619253
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -2.7926234671860763
pKa (strongest acidic): 13.685413916695513
Number of Rings: 5
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 114778
PeakForestCompound: 000005

Taxonomy as Food Phytochemical

Family: Terpenoids
Class: Diterpenoids
Sub-class: Not Available

Taxonomy as Metabolite

Metabolite Family: Terpenoid metabolites
Metabolite Class: Diterpenoid metabolites
Metabolite Sub-class: Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Kahweol	Terpenoids	Diterpenoids	Not Available	Show Food Phytochemical

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", "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", "Cyclic alcohol", "Furan", "Heteroaromatic compound", "Hydrocarbon derivative", "Naphthofuran", "Organic oxygen compound", "Organooxygen compound", "Oxacycle", "Primary alcohol", "Tertiary alcohol"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(93.03403978,0.4322258293);(133.0653399,0.8392637396);(145.0653399,0.5801341731);(147.08099,1.200588169);(153.0915547,0.4884979729);(155.1072047,0.722602373);(159.08099,0.5588158203);(161.09664,0.8418097425);(167.1072047,0.5179060601);(169.1228548,1.051029147);(181.1228548,0.487013546);(183.1385048,0.722602373);(221.1541549,0.3436164841);(223.169805,0.4696102095);(233.1541549,0.3956206873);(239.1435902,0.5682438739);(243.1748904,0.3395477496);(247.169805,0.4892079818);(253.1592403,0.67974211);(257.1905404,0.4598794149);(265.1592403,0.6713669979);(279.1748904,4.814536171);(283.169805,1.756012742);(285.185455,0.9041716815);(287.1647196,0.5878255659);(289.1803697,0.4834238429);(297.185455,6.440298107);(297.185455,10.40668708);(299.1647196,0.5505610397);(299.1647196,0.8649450226);(315.1960197,60.33221429)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(93.03403978,4.141062867);(133.0653399,2.178804313);(135.08099,1.297843126);(145.0653399,2.044088176);(147.08099,2.856214246);(155.1072047,1.315507401);(159.08099,1.730852379);(161.09664,2.217863386);(167.1072047,1.246190154);(169.1228548,1.677066922);(183.1385048,1.315507401);(203.1435902,2.102912635);(205.1592403,1.363602073);(221.1541549,2.203730967);(223.169805,2.846905975);(227.1435902,1.195264044);(229.1592403,1.620228792);(233.1541549,1.67638075);(239.1435902,2.024138299);(247.169805,1.828646723);(253.1592403,2.135868998);(279.1748904,11.03073652);(281.1541549,1.355724982);(283.169805,2.277306548);(285.185455,1.19368524);(287.1647196,1.58256803);(289.1803697,2.416263467);(297.185455,10.91871627);(297.185455,7.250540965);(299.1647196,3.072802711);(315.1960197,17.88297564)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(41.03912516,4.966191479);(43.05477522,4.678175181);(51.0234751,5.293826287);(53.03912516,2.313549434);(55.05477522,4.731519199);(79.05477522,3.932406944);(93.07042529,3.812058044);(105.0704253,2.221751935);(107.0860754,3.196093947);(133.0653399,3.055425129);(135.08099,2.634838972);(137.09664,3.17175193);(147.1173755,3.616334426);(151.0759046,2.196844793);(151.1122901,2.923394567);(159.08099,2.247084223);(161.09664,3.043870797);(163.1122901,2.356805315);(165.1279402,3.813536615);(201.1279402,2.445355654);(205.1592403,2.975064601);(209.1330255,2.30652872);(227.1435902,2.782574697);(241.1592403,2.933502634);(243.1748904,4.064814646);(253.1592403,3.724513595);(265.1592403,3.378717192);(267.1748904,2.578641311);(279.1748904,3.298255929);(281.1541549,3.132178411);(299.1647196,2.174393391)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(15.0234751,0.3302862081);(17.00273965,0.3562410135);(25.00782503,0.0510186926);(29.00273965,0.1342613946);(31.01838972,0.1519236673);(73.0289544,0.0544976568);(91.01838972,0.0442908915);(131.0496898,0.1549390164);(145.0653399,0.0656310854);(153.0915547,0.1447745954);(159.08099,0.1549390164);(167.1072047,0.0626364401);(181.1228548,0.1447745954);(239.1435902,0.0767084712);(241.1592403,0.037256483);(251.1435902,0.0460694388);(253.1592403,0.1523280226);(255.1748904,0.0928169214);(263.1435902,0.4000288418);(265.1592403,4.310366378);(267.1385048,0.0480380015);(271.169805,0.1131020751);(277.1592403,1.427523199);(281.1541549,1.883613051);(283.169805,9.634974583);(285.1490695,0.3408635749);(287.1647196,0.328850005);(295.169805,5.718875792);(295.169805,3.845857335);(297.1490695,0.6662822067);(313.1803697,69.02623135)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(17.00273965,0.5225107139);(41.00273965,0.4131867197);(43.01838972,0.4371721261);(67.01838972,0.244570404);(91.01838972,0.1348783848);(131.0496898,0.2162538151);(153.0915547,0.1646679242);(159.08099,0.2162538151);(181.1228548,0.1646679242);(239.1435902,0.3688053753);(241.1592403,0.1773611826);(251.1435902,0.2716964627);(253.1592403,0.5484180778);(255.1385048,0.1391800852);(255.1748904,0.2601006285);(257.1541549,0.1149867253);(263.1435902,1.472518683);(265.1592403,14.42925472);(267.1385048,0.3174635989);(269.1541549,0.1329014289);(271.169805,0.1955649603);(277.1592403,1.026111174);(281.1541549,10.22236082);(283.1334195,0.3348485819);(283.169805,20.53170161);(285.1490695,0.4936622918);(287.1647196,0.5072525318);(295.169805,5.461064672);(295.169805,5.917475439);(297.1490695,1.85590377);(313.1803697,32.70720535)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(67.01838972,5.473410938);(69.03403978,1.438385095);(71.04968984,2.054091386);(91.01838972,1.41516327);(237.1279402,1.084453832);(239.1072047,0.8951906879);(239.1435902,4.022258359);(241.1592403,2.619958106);(249.1279402,2.121648623);(251.1072047,0.9023993523);(251.1435902,11.83568009);(253.1228548,3.85152459);(253.1592403,10.03308264);(255.1385048,4.727662257);(257.1541549,2.508702462);(257.1541549,2.044906302);(265.1228548,1.13442985);(265.1228548,1.068156551);(265.1592403,6.030241039);(267.1385048,4.073640993);(267.1385048,3.097080449);(269.1541549,0.9301396092);(271.169805,0.9289922033);(281.1541549,5.536823129);(283.1334195,1.851366982);(283.169805,9.048085032);(285.1490695,1.923109384);(287.1647196,1.662496547);(297.1490695,2.896244253);(297.1490695,1.771504778);(313.1803697,1.019171218)

Food Sources

Name	Group
Arabica coffee	Coffee and coffee products	Publications	Show
Coffee	Coffee and coffee products	Publications	Show
Robusta coffee	Coffee and coffee products	Publications	Show

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
Kahweol	Arabica coffee	Coffee and coffee products	Publications	Show
Kahweol	Coffee	Coffee and coffee products	Publications	Show
Kahweol	Robusta coffee	Coffee and coffee products	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food Phytochemical	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
Kahweol	Kahweol	human	urine	unchanged	Not Available	Not Available	1-5%	C₂₀H₂₆O₃	314.188194697	Detailed Intervention Studies	Publications
Kahweol	Kahweol glucuronide	human	urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₂₆H₃₄O₉	490.5518874		Publications
Kahweol	Kahweol sulfate	human	urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₂₀H₂₆O₆S	394.4883325		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Kahweol