metabolite

Showing entry for Isovanillic acid

Identification

PhytoHub ID
PHUB001276
Name
Isovanillic acid
Systematic Name
3-hydroxy-4-methoxybenzoic acid
Synonyms
  • 3-Hydroxy-4-methoxybenzoic acid
CAS Number
645-08-9
Average Mass
168.148
Monoisotopic Mass
168.042258738
Chemical Formula
C8H8O4
IUPAC Name
3-hydroxy-4-methoxybenzoic acid
InChI Key
LBKFGYZQBSGRHY-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
SMILES
COC1=CC=C(C=C1O)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
4.42e+00 g/l
LogS (ALOGPS)
-1.58
LogP (ALOGPS)
1.81
Hydrogen Acceptors
4
Hydrogen Donors
2
Rotatable Bond Count
2
Polar Surface Area
66.76
Refractivity
41.758300000000006
Polarizability
15.89435978507997
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-4.911668652620585
pKa (strongest acidic)
4.147477192001137
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Benzoic and hippuric acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Cyanidin 3-O-glucosidePolyphenolsFlavonoidsAnthocyaninsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Benzene and substituted derivatives
Super-class
Benzenoids
Sub-class
Benzoic acids and derivatives
Direct Parent Name
P-methoxybenzoic acids and derivatives
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Alkyl aryl ethers", "Anisoles", "Benzoic acids", "Benzoyl derivatives", "Carboxylic acids", "Hydrocarbon derivatives", "Hydroxybenzoic acid derivatives", "Methoxybenzenes", "Methoxyphenols", "Monocarboxylic acids and derivatives", "Organic oxides", "Phenoxy compounds"]
External Descriptor Annotations
["methoxybenzoic acid", "monohydroxybenzoic acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Alkyl aryl ether", "Anisole", "Aromatic homomonocyclic compound", "Benzoic acid", "Benzoyl", "Carboxylic acid", "Carboxylic acid derivative", "Ether", "Hydrocarbon derivative", "Hydroxybenzoic acid", "Methoxybenzene", "Methoxyphenol", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "P-methoxybenzoic acid or derivatives", "Phenol", "Phenol ether", "Phenoxy compound"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
GC-MSEI-BpositiveNot AvailableView Spectrum(97.0,8.33);(108.0,1.19);(123.0,2.31);(125.0,9.61);(151.0,11.26);(152.0,1.2);(153.0,46.81);(154.0,3.7);(168.0,99.99);(169.0,9.95);(170.0,1.26)
GC-MSEI-BpositiveNot AvailableView Spectrum(97.0,8.33);(108.0,1.19);(123.0,2.31);(125.0,9.61);(151.0,11.26);(152.0,1.2);(153.0,46.81);(154.0,3.7);(168.0,99.99);(169.0,9.95);(170.0,1.26)
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(23.99945142,0.9633612459);(25.00727602,1.85728104);(27.02292522,1.862784902);(44.99710422,1.480222568);(67.98927962,1.093612741);(69.03348852,1.195047349);(82.00492882,1.212463046);(83.01275342,1.959066115);(95.04913772,1.313277459);(96.02057802,1.23465331);(97.02840262,1.023662765);(109.0284026,2.696828173);(121.0284026,1.333462312);(121.9998429,1.330697493);(122.0362272,6.67975576);(123.0076675,1.193766993);(123.0440518,4.8059248);(124.0154921,1.855859768);(124.0518764,9.029203721);(125.0233167,2.496499752);(135.0076675,1.636639838);(138.0311413,3.766514262);(139.0389659,1.828627519);(140.0467905,2.787760993);(150.0311413,7.165410025);(151.0389659,6.372473346);(152.0104062,3.289471329);(153.0182308,5.398961261);(167.03388,2.978126779);(168.0417046,16.62491608);(169.0451121,1.533667251)
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(27.02292522,1.22470782);(59.03115062,1.466272821);(71.03115062,0.9752159486);(72.03897522,0.8314286554);(73.01041552,0.7986531898);(73.04679982,11.61080071);(74.04796012,0.9934925175);(75.02606472,1.368152819);(89.04171392,2.134030762);(113.0417139,0.8029583479);(115.0573631,1.577313552);(151.0389659,1.128482874);(153.036628,0.9824333875);(169.0679264,1.151478361);(179.0522772,1.263944384);(181.0679264,1.545438179);(195.0835756,1.53326891);(207.0471913,0.9842750866);(211.0784897,0.8974527474);(223.0784897,2.931011206);(225.0577546,2.090285632);(238.0655792,0.8413394497);(239.0734038,3.21974833);(240.0812284,1.507119863);(241.089053,1.764927502);(253.0710659,0.855117279);(267.0867151,1.408542565);(296.0894538,1.455463219);(297.0972784,7.162221161);(298.0991502,1.800865815);(312.1207522,1.068434439)
Predicted GC-MSGC-MSEiNot AvailableView Spectrum(23.99945142,0.8233939767);(25.00727602,1.195258943);(27.02292522,1.428826313);(39.99436552,0.8471961045);(41.00219012,0.7520622947);(43.01783932,0.8269666734);(44.99710422,1.082803445);(82.00492882,0.8936013409);(83.01275342,1.383537243);(94.00492882,0.7769984002);(95.01275342,0.8125094164);(96.02057802,0.9708812461);(97.02840262,0.8150753112);(109.0284026,1.968947406);(121.9998429,0.7491656642);(122.0362272,4.923068564);(123.0440518,3.376208104);(124.0154921,1.10542011);(124.0518764,6.810701745);(125.0233167,1.514968451);(135.0076675,1.511240334);(138.0311413,2.202164463);(139.0389659,1.233626015);(140.0467905,1.613213501);(150.0311413,7.660216867);(151.0389659,3.670852292);(152.0104062,2.241540647);(153.0182308,3.97673389);(167.03388,2.194918924);(168.0417046,12.29718419);(169.0451121,1.134429105)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(17.03912516,0.033409387);(31.01838972,0.0061726637);(41.03912516,0.0016096031);(44.99765427,0.0158425278);(47.04968984,0.0204847755);(51.0234751,0.0016485372);(55.01838972,0.0143023903);(57.03403978,0.0911659188);(67.01838972,0.0131218851);(71.01330434,0.0604968449);(71.04968984,0.0754773888);(73.0289544,0.0867803261);(79.01838972,0.0057086757);(80.99765427,0.0072186961);(81.03403978,0.0372262948);(83.04968984,0.0017909277);(95.01330434,0.0641593185);(95.04968984,0.0389650654);(97.0289544,0.2785234052);(99.00821896,0.0214421861);(99.04460446,0.0449897584);(109.0289544,0.236641147);(113.023869,0.0443408037);(123.008219,0.0257786086);(125.023869,0.6664500473);(125.0602545,3.90458207);(127.0395191,0.2012883933);(139.0395191,0.7285407506);(143.0344337,0.303593896);(153.0187836,0.4645841424);(169.0500838,92.50366357)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(31.01838972,0.0288603665);(43.01838972,0.0160885405);(44.99765427,0.0654497122);(47.04968984,0.6800284608);(51.0234751,0.1175488727);(53.03912516,0.038390231);(55.01838972,0.0618093835);(57.03403978,0.5696605296);(67.01838972,0.0431907116);(71.01330434,0.2017791465);(71.04968984,0.2968233113);(73.0289544,0.1252347519);(79.01838972,0.1339668677);(80.99765427,0.0584553545);(81.03403978,0.2680868148);(83.04968984,0.0179766578);(95.01330434,0.1280916899);(95.04968984,1.906083019);(97.0289544,0.5393683736);(99.00821896,0.1915024255);(99.04460446,0.1367918011);(109.0289544,1.333487027);(113.023869,0.0880957337);(123.008219,0.1842627807);(125.023869,0.8470856562);(125.0602545,13.75476224);(127.0395191,0.3307537273);(139.0395191,1.369790592);(143.0344337,0.5287630722);(153.0187836,1.098238776);(169.0500838,74.83957337)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(27.0234751,0.2964635704);(44.99765427,0.2960009262);(51.0234751,8.608174921);(53.03912516,2.476547442);(55.01838972,2.13780678);(57.03403978,0.3115773317);(67.01838972,5.642218532);(69.03403978,0.6926229372);(71.01330434,2.586740513);(71.04968984,0.5904116086);(73.0289544,0.7725278974);(79.01838972,2.857707454);(81.03403978,4.697588207);(83.01330434,0.9893090745);(83.04968984,0.4655192977);(95.01330434,3.882613643);(95.04968984,4.929044696);(97.0289544,9.109131517);(99.04460446,1.751678967);(109.0289544,18.87455158);(111.008219,0.2589991078);(113.023869,1.224020103);(123.008219,0.9683035005);(125.023869,3.315132522);(125.0602545,7.058857904);(127.0031336,0.3953551533);(127.0395191,0.8387487409);(139.0395191,3.156793423);(143.0344337,1.719872055);(153.0187836,5.347777167);(169.0500838,3.747903432)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(15.0234751,0.0524651452);(39.0234751,0.0185043354);(41.00273965,0.0169382329);(43.01838972,0.0050351544);(49.00782503,0.0063613784);(51.0234751,0.0175442477);(53.00273965,0.0119917205);(55.01838972,0.233171387);(65.00273965,0.0056937125);(67.01838972,0.0073289518);(68.99765427,0.021957475);(69.03403978,0.2016908452);(71.01330434,0.0669003694);(79.01838972,0.0345873519);(81.03403978,0.0253794319);(92.99765427,0.0035876722);(93.03403978,0.2146801711);(95.01330434,0.0629708122);(96.99256889,0.0263490654);(97.0289544,0.1215666125);(107.0133043,2.575744224);(108.9925689,0.0012774957);(111.008219,0.0513297723);(120.9925689,0.0073781303);(123.008219,0.0494190426);(123.0446045,25.45458926);(125.023869,0.0917586478);(137.023869,0.2262697125);(141.0187836,0.4727927954);(151.0031336,0.7337920583);(167.0344337,69.18094479)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(15.0234751,0.105678002);(41.00273965,0.1383696186);(43.01838972,0.0423898795);(49.00782503,0.0934835041);(51.0234751,0.3645164932);(53.00273965,0.1003390644);(55.01838972,0.1158083117);(65.00273965,0.1435438839);(67.01838972,0.6648452284);(68.99765427,0.2715346456);(69.03403978,0.0827013372);(71.01330434,0.1433340974);(77.00273965,0.2847532757);(79.01838972,0.2658837017);(81.03403978,0.7344654854);(92.99765427,0.1227167676);(93.03403978,2.305730433);(95.01330434,0.6391882463);(96.99256889,0.128147896);(97.0289544,0.7354164322);(107.0133043,17.4881868);(108.9925689,0.0482229082);(111.008219,0.4755442595);(120.9925689,0.4021003781);(123.008219,1.015204134);(123.0446045,33.22801042);(125.023869,0.8707787399);(137.023869,1.090254265);(141.0187836,0.6458131146);(151.0031336,5.485711769);(167.0344337,31.76732691)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,1.396103419);(43.01838972,0.297303003);(44.99765427,1.024227851);(49.00782503,1.139254519);(51.0234751,2.460429473);(53.00273965,1.236616366);(55.01838972,2.232940354);(65.00273965,1.740978823);(67.01838972,2.339106517);(68.99765427,3.063762278);(71.01330434,1.116647623);(77.00273965,1.975081924);(79.01838972,2.71607268);(80.99765427,0.9959550518);(81.03403978,1.366416806);(92.99765427,1.974656026);(93.03403978,6.342326588);(95.01330434,4.044702562);(96.99256889,0.5509630375);(97.0289544,1.461375293);(107.0133043,29.33882262);(108.9925689,1.136624708);(111.008219,1.066525617);(120.9925689,4.412073833);(123.008219,2.090841393);(123.0446045,5.726091875);(125.023869,1.443362842);(137.023869,2.415702122);(141.0187836,0.3907024748);(151.0031336,10.6035771);(167.0344337,1.900755228)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(95.04914,16.13);(95.04914,16.13);(123.04406,50.32);(123.04406,50.32);(123.04406,50.32);(123.04406,50.32);(123.04406,50.32);(123.04406,50.32);(123.04406,50.32);(123.04406,50.32);(123.04406,50.32);(125.05971,97.01);(125.05971,97.01);(125.05971,97.01);(125.05971,97.01);(125.05971,97.01);(125.05971,97.01);(125.05971,97.01);(151.03897,40.05);(151.03897,40.05);(151.03897,40.05);(151.03897,40.05);(151.03897,40.05);(151.03897,40.05);(169.04954,100.0);(169.04954,100.0);(169.04954,100.0);(169.04954,100.0);(169.04954,100.0);(169.04954,100.0);(169.04954,100.0)
Predicted LC-MS/MSNot AvailablePositivemediumView Spectrum(44.99711,17.95);(79.01784,13.14);(79.01784,13.14);(79.01784,13.14);(81.03349,14.47);(81.03349,14.47);(81.03349,14.47);(81.03349,14.47);(93.03349,12.37);(95.04914,18.81);(95.04914,18.81);(97.02841,11.06);(97.02841,11.06);(97.02841,11.06);(109.02841,19.51);(109.02841,19.51);(109.02841,19.51);(109.02841,19.51);(123.04406,64.5);(123.04406,64.5);(123.04406,64.5);(123.04406,64.5);(123.04406,64.5);(123.04406,64.5);(123.04406,64.5);(123.04406,64.5);(123.04406,64.5);(125.05971,34.58);(125.05971,34.58);(125.05971,34.58);(125.05971,34.58);(125.05971,34.58);(125.05971,34.58);(125.05971,34.58);(141.05462,11.4);(141.05462,11.4);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(169.04954,49.26);(169.04954,49.26);(169.04954,49.26);(169.04954,49.26);(169.04954,49.26);(169.04954,49.26);(169.04954,49.26)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(27.02293,15.92);(39.02293,100.0);(41.00219,12.95);(41.03858,8.32);(43.01784,26.91);(45.03349,10.02);(45.03349,10.02);(51.02293,59.26);(53.03858,10.13);(65.00219,8.15);(67.01784,10.1);(67.01784,10.1);(79.01784,21.81);(79.01784,21.81);(79.01784,21.81);(81.03349,34.19);(81.03349,34.19);(81.03349,34.19);(81.03349,34.19);(95.01276,10.4);(95.01276,10.4);(95.01276,10.4);(95.01276,10.4);(97.02841,11.29);(97.02841,11.29);(97.02841,11.29);(109.02841,10.59);(109.02841,10.59);(109.02841,10.59);(109.02841,10.59);(123.04406,9.15);(123.04406,9.15);(123.04406,9.15);(123.04406,9.15);(123.04406,9.15);(123.04406,9.15);(123.04406,9.15);(123.04406,9.15);(123.04406,9.15)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(123.04515,100.0);(123.04515,100.0);(123.04515,100.0);(123.04515,100.0);(123.04515,100.0);(123.04515,100.0);(123.04515,100.0);(167.03498,53.86);(167.03498,53.86);(167.03498,53.86);(167.03498,53.86);(167.03498,53.86)
Predicted LC-MS/MSNot AvailableNegativemediumView Spectrum(93.03459,19.01);(93.03459,19.01);(107.01385,100.0);(107.01385,100.0);(123.04515,32.07);(123.04515,32.07);(123.04515,32.07);(123.04515,32.07);(123.04515,32.07);(123.04515,32.07);(123.04515,32.07);(167.03498,17.16);(167.03498,17.16);(167.03498,17.16);(167.03498,17.16);(167.03498,17.16)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00329,63.04);(53.00329,51.91);(55.01894,39.21);(55.01894,39.21);(67.01894,22.98);(67.01894,22.98);(69.03459,16.85);(69.03459,16.85);(79.01894,40.48);(79.01894,40.48);(93.03459,58.33);(93.03459,58.33);(95.01385,36.77);(95.01385,36.77);(95.01385,36.77);(95.05024,30.26);(95.05024,30.26);(107.01385,100.0);(107.01385,100.0);(123.00877,25.02);(123.00877,25.02);(123.00877,25.02)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Cyanidin 3-O-glucoside Isovanillic acidhumanfeces, serum, urineNot AvailableNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Publications
Orange flavanones Isovanillic acidhumanurinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Back