metabolite

Showing entry for 14-Hydroxycaryophyllene-5,6-oxide

Identification

PhytoHub ID
PHUB000928
Name
14-Hydroxycaryophyllene-5,6-oxide
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
236.355
Monoisotopic Mass
236.177630013
Chemical Formula
C15H24O2
IUPAC Name
[(1R,10S)-4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-12-yl]methanol
InChI Key
XLKXIWMHACWINL-ILDWOOSOSA-N
InChI Identifier
InChI=1S/C15H24O2/c1-10-4-5-13-15(3,17-13)7-6-12-11(10)8-14(12,2)9-16/h11-13,16H,1,4-9H2,2-3H3/t11-,12-,13?,14?,15?/m1/s1
SMILES
[H][C@]12CC(C)(CO)[C@]1([H])CCC1(C)OC1CCC2=C
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
9.23e-02 g/l
LogS (ALOGPS)
-3.41
LogP (ALOGPS)
2.30
Hydrogen Acceptors
2
Hydrogen Donors
1
Rotatable Bond Count
1
Polar Surface Area
32.76
Refractivity
67.9876
Polarizability
27.891434217505093
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-1.4131978016769473
pKa (strongest acidic)
18.16628022543005
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
Yes
MDDR-like Rule
No

Taxonomy as Metabolite

Family
Terpenoid metabolites
Class
Sesquiterpenoid metabolites
Sub-class
Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Caryophyllen-betaTerpenoidsSesquiterpenoidsNot AvailableShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Prenol lipids
Super-class
Lipids and lipid-like molecules
Sub-class
Sesquiterpenoids
Direct Parent Name
Sesquiterpenoids
Alternative Parent Names
["Dialkyl ethers", "Epoxides", "Hydrocarbon derivatives", "Oxacyclic compounds", "Primary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["Alcohol", "Aliphatic heteropolycyclic compound", "Caryophyllane sesquiterpenoid", "Dialkyl ether", "Ether", "Hydrocarbon derivative", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxirane", "Primary alcohol", "Sesquiterpenoid"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(31.01783932,2.272757205);(39.02292522,1.575803023);(41.03857442,1.363774997);(57.03348852,1.348914521);(71.04913772,4.893598745);(72.05696232,1.129429533);(147.1168204,1.660218241);(149.0960853,3.982238199);(161.0960853,1.578770271);(162.1039099,5.821779294);(163.1117345,19.7093632);(164.1151448,2.478616489);(164.1195591,7.351528253);(165.1273837,5.413855883);(166.1352083,1.148395595);(167.1430329,1.366253623);(169.1586821,1.206565722);(176.1195591,1.417134645);(177.1273837,9.187446654);(178.1307958,1.260998055);(178.1352083,2.78810874);(179.1430329,2.9757153);(180.1508575,1.076112228);(182.1665067,1.090830677);(204.1508575,1.18475152);(205.1586821,2.275974553);(218.1665067,1.728950745);(219.1743313,1.752189114);(220.1457716,2.856313725);(221.1535962,4.318144682);(236.17707,1.78546657)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(41.03912516,0.2144559846);(53.03912516,0.1971555382);(55.05477522,0.2518540337);(57.07042529,0.2029783602);(71.04968984,0.2054991835);(73.06533991,0.5238323229);(75.08098997,0.123159425);(95.08607535,0.1418421618);(97.06533991,0.2562453165);(97.10172542,0.1925057388);(99.08098997,0.3444459607);(111.08099,0.5396339483);(113.09664,0.7951013682);(123.08099,0.2151836682);(125.09664,0.3881974225);(137.09664,0.443602733);(139.1122901,0.4873666702);(161.1330255,0.1835629407);(163.1122901,0.6232114535);(165.1279402,0.9993793948);(167.1435902,0.2544176369);(177.1279402,0.6769858427);(179.1435902,1.270327531);(181.1592403,0.5776913323);(201.1643257,1.782526669);(203.1435902,0.4019525647);(205.1592403,1.449869266);(207.1748904,0.6960240794);(219.1748904,41.79112246);(221.1541549,0.7572422071);(237.185455,43.01262678)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(41.03912516,1.164180441);(53.03912516,1.104750639);(57.03403978,0.6113388292);(57.07042529,0.8038812554);(59.04968984,0.8193310325);(71.04968984,0.6529978527);(73.06533991,0.8398611959);(95.08607535,0.5884023204);(97.06533991,1.150916449);(99.08098997,1.000571105);(107.0860754,0.7592311182);(111.08099,1.068057938);(113.09664,1.258355095);(123.08099,0.7789810532);(125.09664,1.150468752);(137.09664,1.769607352);(139.1122901,1.257324115);(151.1122901,1.049914547);(161.1330255,2.187181292);(163.1122901,1.541679625);(163.1486756,0.5978025839);(165.1279402,1.497386621);(177.1279402,1.993288036);(179.1435902,3.227003304);(201.1643257,12.4351975);(203.1435902,1.771206618);(205.1592403,1.411688822);(207.1748904,1.609398293);(219.1748904,40.45625335);(221.1541549,0.9773869352);(237.185455,12.46635593)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(41.03912516,5.331696854);(43.05477522,2.718856769);(51.0234751,2.843091299);(53.03912516,10.1746712);(55.05477522,8.774863391);(57.07042529,3.076473951);(67.05477522,2.828295472);(79.05477522,2.041226715);(95.08607535,3.046312258);(97.06533991,3.607391907);(97.10172542,1.855764855);(99.08098997,1.763275159);(107.0860754,7.083848546);(109.1017254,2.002832368);(111.08099,2.356726072);(121.1017254,5.229203525);(123.08099,2.179747261);(123.1173755,2.47909054);(125.09664,1.727303819);(133.1017254,1.806494407);(135.1173755,3.128992437);(137.09664,3.179539917);(147.1173755,2.64016194);(151.1122901,1.865901393);(163.1486756,2.42559218);(165.1279402,1.983402305);(179.1435902,2.422885445);(203.1435902,3.355905165);(205.1592403,2.028885569);(219.1748904,2.279617068);(221.1541549,1.761950214)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(17.00273965,0.6572554473);(29.00273965,0.1253003748);(41.03912516,0.1851679386);(53.00273965,0.4948944131);(55.01838972,0.5295890716);(59.04968984,4.139635568);(69.03403978,0.0672993137);(71.04968984,0.4058678526);(73.06533991,0.1166903766);(83.04968984,0.0540742754);(137.09664,0.050101634);(161.09664,0.0740366302);(161.1330255,0.0629016014);(163.1122901,0.5563732283);(165.1279402,0.1400916815);(175.1122901,0.4046894087);(177.1279402,1.419665385);(179.1435902,0.5187679869);(181.1592403,0.1722202762);(187.1486756,1.04311962);(189.1279402,0.5719550426);(199.1486756,0.5394567519);(201.1279402,0.0979020939);(203.1435902,0.3091211404);(205.1228548,0.0619155213);(205.1592403,9.170954577);(207.1385048,0.4978597365);(209.1541549,0.3183917853);(217.1592403,14.50573775);(219.1385048,1.864057389);(235.169805,60.84490613)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(17.00273965,2.448564194);(55.01838972,0.2930910966);(59.04968984,0.1837325809);(71.04968984,0.6964624278);(83.04968984,0.1874690379);(97.06533991,0.3112609372);(137.09664,0.589985943);(139.1122901,0.2918656501);(149.09664,0.2881753926);(151.1122901,0.6946034584);(153.1279402,0.1882177622);(161.09664,0.2232798248);(163.1122901,1.113229306);(175.1122901,0.4877507471);(177.1279402,1.432036462);(179.1435902,0.5101477687);(187.1486756,0.5029435605);(189.1279402,1.561110003);(191.1435902,0.4463753206);(193.1228548,0.1973405706);(195.1385048,0.2685284218);(199.1486756,0.4180858197);(201.1279402,0.3663389327);(203.1435902,1.473832304);(205.1228548,1.560344152);(205.1592403,25.78594894);(207.1385048,1.298429694);(209.1541549,1.340006915);(217.1592403,16.71516471);(219.1385048,4.279376228);(235.169805,33.84630185)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(39.0234751,4.418218623);(55.01838972,9.846109079);(57.03403978,2.8373242);(69.03403978,2.263426712);(71.04968984,1.328415831);(81.07042529,1.522815063);(83.04968984,2.624975207);(85.06533991,1.292993363);(109.0653399,1.743564079);(111.08099,1.402051214);(123.08099,1.172933814);(137.09664,1.526941264);(147.1173755,1.715135853);(149.1330255,2.787321016);(151.1122901,2.196076253);(163.1122901,4.228441325);(175.1122901,4.131802798);(177.1279402,6.687853589);(179.1435902,3.887685945);(187.1122901,2.349465386);(189.1279402,12.66175764);(191.1072047,2.891851997);(193.1228548,2.118984634);(201.1279402,1.263603082);(203.1435902,1.482821766);(205.1592403,6.315395284);(207.1385048,1.989440707);(209.1541549,1.611413263);(217.1592403,1.792657766);(219.1385048,6.664853008);(235.169805,1.24367024)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
Caryophyllen-betaGrapeFruit, Berries PublicationsShow
Caryophyllen-betaMandarin orange (Clementine, Tangerine)Fruit, Citrus PublicationsShow
Caryophyllen-betaPepperHerbs and Spices PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caryophyllen-beta 14-Hydroxycaryophyllene-5,6-oxiderabbiturine (major)Not AvailableNot AvailableNot AvailableNot AvailableC15H24O2236.177630013 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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