precursor metabolite

Showing entry for Vanillic acid

Identification

PhytoHub ID
PHUB000316
Name
Vanillic acid
Systematic Name
4-hydroxy-3-methoxybenzoic acid
Synonyms
  • 3-Methoxy-4-hydroxybenzoic acid
  • 4-Hydroxy-3-methoxybenzoic acid
  • p-Vanillic acid
CAS Number
499-76-3
Average Mass
168.148
Monoisotopic Mass
168.042258738
Chemical Formula
C8H8O4
IUPAC Name
vanillic acid
InChI Key
WKOLLVMJNQIZCI-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
SMILES
COC1=CC(=CC=C1O)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
5.70e+00 g/l
LogS (ALOGPS)
-1.47
LogP (ALOGPS)
1.70
Hydrogen Acceptors
4
Hydrogen Donors
2
Rotatable Bond Count
2
Polar Surface Area
66.76
Refractivity
41.7583
Polarizability
15.868081533318291
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-4.901377890748089
pKa (strongest acidic)
4.155416072405769
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy

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

Spectra

Record IDSourceDescriptionView
JP008196MassBankEI-B Spectrum - -, [M]+*View Spectra
KO001150MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO001151MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO001152MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO001153MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO001154MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
ML005851MassBankLC-ESI-ITFT Spectrum - 50 % (nominal), unspecifiedView Spectra

Food Sources

NameGroup
American cranberryFruit, Berries PublicationsShow
Olive, blackFruit, Drupes PublicationsShow
Olive, greenFruit, Drupes PublicationsShow
StrawberryFruit, Berries PublicationsShow
VanillaHerbs and Spices PublicationsShow
White wineBeverages, Alcoholic PublicationsShow
PrecursorFood SourceFood Source Group
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
Ferulic acidAmerican cranberryFruit, Berries PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBilberryFruit, Berries PublicationsShow
Ferulic acidBlack mulberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideBlackberryFruit, Berries PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
Ferulic acidBlackberryFruit, Berries PublicationsShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
Dihydrocaffeic acidBlueberryFruit, BerriesShow
Ferulic acidBlueberryFruit, Berries PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
Dihydrocaffeic acidBroccoliVegetables, CabbagesShow
Ferulic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
Dihydrocaffeic acidCiderBeverages, AlcoholicShow
Ferulic acidCocoa beanCocoa and cocoa products PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
Dihydrocaffeic acidCoffeeCoffee and coffee productsShow
Ferulic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCommon beanPulses and beans PublicationsShow
Ferulic acidCommon walnutNuts PublicationsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidCommon wheatCereals and cereal productsShow
Ferulic acidCommon wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidCornCereals and cereal productsShow
Ferulic acidCornCereals and cereal products PublicationsShow
Ferulic acidDateFruit, Other fruits PublicationsShow
Caffeic acidEggplantVegetables, Fruit vegetables PublicationsShow
Ferulic acidEggplantVegetables, Fruit vegetables PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
Ferulic acidEuropean cranberryFruit, Berries PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
Ferulic acidFennelHerbs and Spices PublicationsShow
Ferulic acidGrapefruitFruit, Citrus PublicationsShow
Dihydrocaffeic acidGrapesFruit, BerriesShow
Ferulic acidHard wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidLemonFruit, CitrusShow
Cyanidin 3-O-glucosideLettuceVegetables, Leaf vegetables PublicationsShow
Dihydrocaffeic acidLettuceVegetables, Leaf vegetablesShow
Dihydrocaffeic acidLimeFruit, CitrusShow
Caffeic acidMateBeverages, Non-alcoholic PublicationsShow
Cyanidin 3-O-glucosideOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, blackFruit, Drupes PublicationsShow
Ferulic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOrange juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
Cyanidin 3-O-glucosidePomegranate juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidRapeseedOilseed crops PublicationsShow
Ferulic acidRed raspberryFruit, Berries PublicationsShow
Ferulic acidRiceCereals and cereal products PublicationsShow
Ferulic acidRosemaryHerbs and Spices PublicationsShow
Ferulic acidRye breadCereals and cereal products PublicationsShow
Dihydrocaffeic acidSpinachVegetables, Leaf vegetablesShow
Ferulic acidSpinachVegetables, Leaf vegetables PublicationsShow
Cyanidin 3-O-glucosideStrawberryFruit, Berries PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
Ferulic acidStrawberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideSweet cherryFruit, Drupes PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
Ferulic acidSweet orangeFruit, Citrus PublicationsShow
Ferulic acidTarragonHerbs and Spices PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
Ferulic acidTomatoVegetables, Fruit vegetables PublicationsShow
Dihydrocaffeic acidWheat breadCereals and cereal productsShow
Ferulic acidWhite wineBeverages, Alcoholic PublicationsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Cyanidin 3-O-glucoside Vanillic acidhumanfaeces, serum, urineNot AvailableC8H8O4168.042258738 Publications
Caffeic acid Vanillic acidhumanurinehost metabolismC8H8O4168.042258738 Publications
Dihydrocaffeic acid Vanillic acidraturineNot AvailableC8H8O4168.042258738
Ferulic acid Vanillic acidhuman raturineNot AvailableC8H8O4168.042258738 Publications
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