metabolite

Showing entry for Vanillic acid-4-O-sulfate

Identification

PhytoHub ID
PHUB001294
Name
Vanillic acid-4-O-sulfate
Systematic Name
3-methoxybenzoic acid-4-sulfate
Synonyms
  • 3-Methoxybenzoic acid-4-sulfate
  • Vanillic acid-4-sulfate
CAS Number
71235-86-4
Average Mass
248.21
Monoisotopic Mass
247.999073772
Chemical Formula
C8H8O7S
IUPAC Name
3-methoxy-4-(sulfooxy)benzoic acid
InChI Key
TXRKUXPAEPOCIX-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C8H8O7S/c1-14-7-4-5(8(9)10)2-3-6(7)15-16(11,12)13/h2-4H,1H3,(H,9,10)(H,11,12,13)
SMILES
COC1=C(OS(O)(=O)=O)C=CC(=C1)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
2.38e+00 g/l
LogS (ALOGPS)
-2.02
LogP (ALOGPS)
-0.77
Hydrogen Acceptors
6
Hydrogen Donors
2
Rotatable Bond Count
4
Polar Surface Area
110.13000000000001
Refractivity
51.75010000000001
Polarizability
21.064637082458326
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-4.929206541662974
pKa (strongest acidic)
-2.5583886644089846
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
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Vanillic acidPolyphenolsPhenolic acidsHydroxybenzoic acidsShow 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
M-methoxybenzoic acids and derivatives
Alternative Parent Names
["Alkyl aryl ethers", "Anisoles", "Benzoic acids", "Benzoyl derivatives", "Carboxylic acids", "Hydrocarbon derivatives", "Methoxybenzenes", "Monocarboxylic acids and derivatives", "Organic oxides", "Phenoxy compounds", "Phenylsulfates", "Sulfuric acid monoesters"]
External Descriptor Annotations
Not Available
Substituent Names
["Alkyl aryl ether", "Anisole", "Aromatic homomonocyclic compound", "Arylsulfate", "Benzoic acid", "Benzoyl", "Carboxylic acid", "Carboxylic acid derivative", "Ether", "Hydrocarbon derivative", "M-methoxybenzoic acid or derivatives", "Methoxybenzene", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organic sulfuric acid or derivatives", "Organooxygen compound", "Phenol ether", "Phenoxy compound", "Phenylsulfate", "Sulfate-ester", "Sulfuric acid ester", "Sulfuric acid monoester"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(25.00727602,1.60491708);(55.01783932,1.940254762);(80.96408832,4.360055614);(97.02840262,2.075429241);(122.0362272,2.270325772);(123.0440518,4.262481759);(124.0518764,2.121139399);(134.9746516,3.291029465);(135.9824762,1.638581902);(136.9903008,1.57202986);(138.0311413,2.862949778);(139.0389659,2.903349879);(149.0233167,2.451662999);(150.0311413,3.234636467);(151.0389659,4.490887509);(153.0182308,2.545881437);(166.0260554,3.357360245);(167.03388,4.725489313);(168.0417046,10.05786398);(201.9930395,3.125988658);(203.0008641,1.889318891);(204.0086887,3.277581502);(204.980129,3.146884591);(215.9723044,2.572081198);(217.9879536,2.723106968);(220.0036028,1.562687455);(229.9879536,4.118097474);(230.9957782,5.067216804);(232.9750431,2.466771689);(246.9906923,1.841090792);(247.9985169,6.442847514)
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(27.02292522,0.8408695041);(55.01783932,0.8327006496);(57.03348852,0.8569070542);(59.03115062,0.9681986009);(71.03115062,1.07176525);(73.04679982,10.89541341);(74.04796012,0.9322795192);(75.02606472,1.035366721);(75.06244902,0.833996617);(80.96408832,1.055906366);(89.04171392,3.176746763);(122.9746516,1.059735038);(123.0440518,1.215583206);(134.9746516,1.063000212);(151.0389659,2.164135705);(201.9930395,0.9010413653);(203.0008641,1.365562471);(204.0086887,1.606904289);(225.0577546,2.275743185);(229.9879536,1.055160814);(230.9957782,2.919413441);(238.0655792,0.9395413407);(239.0734038,1.409489609);(240.0812284,1.542947533);(246.9906923,1.118322178);(247.9985169,1.625334048);(249.0063415,1.062173478);(277.0196528,1.164984618);(304.0067423,1.131589516);(305.0145669,3.355800843);(320.0380407,1.341429193)
Predicted GC-MSGC-MSEiNot AvailableView Spectrum(25.00727602,1.238511092);(27.02292522,1.06901302);(44.99710422,0.8534334488);(55.01783932,1.00431072);(80.96408832,1.458492745);(97.02840262,1.128760189);(119.9511778,1.081713618);(122.0362272,0.8291672296);(123.0440518,1.795211608);(124.0518764,0.9367416241);(134.9746516,1.599814832);(139.0389659,1.432840694);(149.0233167,1.595167378);(150.0311413,2.076947555);(151.0389659,1.76837777);(153.0182308,1.062921793);(166.0260554,1.475571038);(167.03388,2.319713711);(168.0417046,4.352002324);(189.9566552,0.8849400922);(201.9930395,1.988944558);(203.0008641,1.261288541);(204.0086887,2.104087632);(204.980129,1.848525202);(217.9879536,1.363201802);(229.9879536,3.700176301);(230.9957782,2.617627875);(231.9672185,0.9744733239);(232.9750431,1.486869768);(246.9906923,1.081254247);(247.9985169,3.989062864)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(27.0234751,0.0019593035);(31.01838972,0.0061118094);(44.99765427,0.0156970392);(51.0234751,0.0033047782);(57.03403978,0.0952334618);(59.04968984,0.023470971);(71.01330434,0.0443280629);(80.96463989,1.33167223);(81.03403978,0.0371546859);(83.04968984,0.0036178961);(95.01330434,0.0025290848);(97.0289544,0.0370362106);(122.9752046,0.0341290559);(125.0602545,0.0336934572);(127.0395191,0.1720433935);(139.0395191,0.0037336939);(146.9752046,0.0124389977);(151.0395191,0.1751237952);(152.9857693,0.0710153975);(153.0187836,0.0411104084);(169.0500838,1.170508449);(174.9701192,0.0062771227);(175.0065047,0.0292881148);(179.0014193,0.2063761053);(188.9857693,0.1628508335);(190.9650338,0.2199850353);(192.9806839,0.040678858);(205.0170694,3.86774493);(218.9963339,0.7215307234);(222.9912486,0.0663828963);(249.0068986,91.3629732)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(43.01838972,0.0201706832);(44.99765427,0.0350935745);(51.0234751,0.037541649);(57.03403978,0.1365612154);(59.04968984,0.1393940155);(71.01330434,0.0946048945);(80.96463989,7.36592028);(81.03403978,0.0786119951);(97.0289544,0.1283234732);(111.008219,0.0190836365);(115.0395191,0.0432389365);(122.9752046,0.0543137776);(125.0602545,3.903811775);(127.0395191,0.281762742);(139.0395191,1.358728677);(141.0187836,0.0214755717);(143.0344337,0.0398453739);(146.9752046,0.0749041201);(151.0395191,12.21633452);(152.9857693,0.0563804793);(153.0187836,2.681958553);(169.0500838,31.89638725);(175.0065047,0.1072251447);(179.0014193,0.1556557533);(188.9857693,0.5809103242);(190.9650338,0.2453907217);(192.9806839,0.0536415827);(205.0170694,6.266856865);(218.9963339,0.5685962218);(222.9912486,0.431123719);(249.0068986,30.90615248)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(27.0234751,0.8970685451);(51.0234751,18.74080164);(53.03912516,5.498208945);(57.03403978,1.288115886);(59.04968984,0.3965268442);(71.01330434,1.582986513);(80.96463989,5.126255623);(81.03403978,6.326274528);(83.04968984,0.690287061);(95.01330434,0.5809472698);(97.0289544,6.848016334);(98.97520458,0.4483777686);(99.04460446,0.4876956714);(122.9752046,0.3920006113);(125.0602545,1.587889497);(127.0395191,0.7557923194);(139.0395191,0.4856888596);(146.9752046,4.380187879);(148.9908546,0.8995091572);(151.0395191,3.12998747);(153.0187836,2.384433098);(169.0500838,2.3616743);(175.0065047,4.450844264);(179.0014193,2.471114451);(188.9857693,9.684580351);(190.9650338,2.185745482);(192.9806839,0.7233347127);(205.0170694,7.049926994);(218.9963339,3.811997315);(222.9912486,0.3842374228);(249.0068986,3.949493191)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(41.00273965,0.0005728719);(49.00782503,0.0030837513);(51.0234751,0.008636094);(55.01838972,0.0699120816);(57.03403978,0.0007418615);(68.99765427,0.0024214591);(79.01838972,0.0273242299);(81.03403978,0.0170474583);(95.01330434,0.0287881117);(97.0289544,0.0031862276);(108.9925689,0.0007341141);(113.023869,0.0014770298);(120.9595545,0.0133228137);(123.0446045,0.8361954079);(125.023869,0.1030735134);(137.023869,0.0326552526);(141.0187836,0.0021012727);(144.9595545,0.0009506821);(146.9752046,0.0016697047);(149.023869,0.0696419337);(150.9701192,0.0014915526);(151.0031336,0.3815938802);(167.0344337,4.255115506);(172.9908546,0.2017817055);(176.9857693,0.1104667254);(186.9701192,2.43106695);(188.9493838,0.0012449311);(190.9650338,0.0084749712);(203.0014193,24.54488832);(216.9806839,0.2175594285);(246.9912486,66.62278016)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(41.00273965,0.0706423781);(49.00782503,0.1415401486);(51.0234751,0.6287959643);(55.01838972,0.2954562381);(68.99765427,0.1487755462);(79.01838972,0.2082245511);(81.03403978,0.7784344105);(95.01330434,0.8177406086);(96.95955451,0.0073944161);(97.0289544,0.0795543084);(108.9925689,0.2744706684);(111.008219,1.409192115);(113.023869,0.0125301232);(120.9595545,0.0293693029);(123.0446045,12.27715028);(125.023869,1.0796092);(137.023869,1.164842239);(141.0187836,0.0801714359);(144.9595545,0.1309575846);(146.9752046,0.530768453);(149.023869,0.7680176284);(151.0031336,10.03679912);(167.0344337,22.14745045);(172.9908546,1.3464888);(176.9857693,0.2376661858);(186.9701192,9.648024572);(188.9493838,0.7381675069);(190.9650338,0.3479984733);(203.0014193,18.246279);(216.9806839,0.6078705154);(246.9912486,15.70961778)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,0.5451701024);(51.0234751,0.1024408714);(53.00273965,0.170197687);(55.01838972,0.4361156877);(57.03403978,0.2304908133);(68.99765427,1.209506272);(79.01838972,0.1295797891);(95.01330434,1.654067464);(96.95955451,0.3893740073);(97.0289544,4.925944966);(108.9925689,1.057798569);(111.008219,1.04405735);(113.023869,0.6367594955);(123.0446045,17.99082626);(125.023869,1.36420628);(137.023869,5.93141983);(144.9595545,0.3026135319);(146.9752046,0.3660348272);(149.023869,1.555119363);(150.9701192,0.2735874241);(151.0031336,36.44662958);(160.9544691,0.1377415248);(167.0344337,9.650248913);(172.9908546,2.335811994);(176.9857693,0.8998677183);(186.9701192,7.032446202);(188.9493838,0.2257088901);(190.9650338,0.145258189);(203.0014193,1.714154794);(216.9806839,0.7066159511);(246.9912486,0.3902056487)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(203.00197,21.74);(203.00197,21.74);(203.00197,21.74);(203.00197,21.74);(246.9918,100.0);(246.9918,100.0)
Predicted LC-MS/MSNot AvailableNegativemediumView Spectrum(80.96519,18.01);(96.9601,100.0);(172.9914,21.46);(203.00197,88.17);(203.00197,88.17);(203.00197,88.17);(203.00197,88.17);(246.9918,80.61);(246.9918,80.61)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(55.01894,5.12);(79.01894,4.52);(80.96519,19.71);(81.03459,16.02);(93.03459,4.97);(96.9601,100.0);(144.9601,5.89);(146.97575,4.45);(172.9914,4.46)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(151.03897,13.68);(151.03897,13.68);(151.03897,13.68);(151.03897,13.68);(151.03897,13.68);(151.03897,13.68);(230.99579,49.09);(230.99579,49.09);(230.99579,49.09);(230.99579,49.09);(230.99579,49.09);(230.99579,49.09);(249.00635,100.0);(249.00635,100.0);(249.00635,100.0);(249.00635,100.0);(249.00635,100.0);(249.00635,100.0)
Predicted LC-MS/MSNot AvailablePositivemediumView Spectrum(123.04406,19.38);(125.05971,29.18);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(167.03389,7.84);(167.03389,7.84);(167.03389,7.84);(167.03389,7.84);(167.03389,7.84);(167.03389,7.84);(169.04954,40.06);(169.04954,40.06);(169.04954,40.06);(169.04954,40.06);(169.04954,40.06);(169.04954,40.06);(169.04954,40.06);(230.99579,13.76);(230.99579,13.76);(230.99579,13.76);(230.99579,13.76);(230.99579,13.76);(230.99579,13.76);(249.00635,9.16);(249.00635,9.16);(249.00635,9.16);(249.00635,9.16);(249.00635,9.16);(249.00635,9.16)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(43.01784,26.74);(51.02293,78.33);(57.03349,11.51);(79.01784,19.51);(79.01784,19.51);(80.96409,18.03);(81.03349,11.72);(81.03349,11.72);(81.03349,11.72);(83.01276,13.64);(85.02841,12.03);(85.02841,12.03);(85.02841,12.03);(95.01276,42.04);(95.01276,42.04);(97.02841,37.82);(97.02841,37.82);(97.02841,37.82);(107.04914,45.28);(109.02841,24.51);(109.02841,24.51);(109.02841,24.51);(123.04406,50.38);(125.02332,21.37);(125.02332,21.37);(125.05971,13.64);(135.04406,17.26);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(151.03897,100.0);(153.01824,50.41);(167.03389,54.15);(167.03389,54.15);(167.03389,54.15);(167.03389,54.15);(167.03389,54.15);(167.03389,54.15);(169.04954,11.96);(169.04954,11.96);(169.04954,11.96);(169.04954,11.96);(169.04954,11.96);(169.04954,11.96);(169.04954,11.96)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Cyanidin 3-O-glucoside Vanillic acid-4-O-sulfatehumanfeces, serum, urineNot AvailableNot AvailableNot AvailableNot AvailableC8H8O7S247.999073772 Publications
Coffee Chlorogenic acids Vanillic acid-4-O-sulfatehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available5-10%C8H8O7S247.999073772 Detailed Intervention Studies Publications
Vanillic acid Vanillic acid-4-O-sulfatehumanplasmahost metabolismNot Available0.5-2µmol/LNot AvailableC8H8O7S247.999073772 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Coffee Chlorogenic acids Vanillic acid-4-O-sulfateMicrobiotaEffect, clusters Publications
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