precursor metabolite

Showing entry for 4'-Hydroxyphenylacetic acid

Identification

PhytoHub ID
PHUB000543
Name
4'-Hydroxyphenylacetic acid
Systematic Name
4'-Hydroxyphenylacetic acid
Synonyms
  • (4-Hydroxyphenyl)acetic acid
  • 2-(4'-Hydroxyphenyl)acetic acid
  • 4-Hydroxyphenylacetic acid
  • 4-hydroxyphenylethanoic acid
CAS Number
156-38-7
Average Mass
152.149
Monoisotopic Mass
152.047344118
Chemical Formula
C8H8O3
IUPAC Name
2-(4-hydroxyphenyl)acetic acid
InChI Key
XQXPVVBIMDBYFF-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
SMILES
OC(=O)CC1=CC=C(O)C=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
7.12e+00 g/l
LogS (ALOGPS)
-1.33
LogP (ALOGPS)
0.93
Hydrogen Acceptors
3
Hydrogen Donors
2
Rotatable Bond Count
2
Polar Surface Area
57.53
Refractivity
39.3465
Polarizability
14.826780263933822
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.958556388425476
pKa (strongest acidic)
3.9984367127077793
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Phenylacetic acids

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Phenolic acid metabolites
Metabolite Sub-class
Phenylacetic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Cyanidin 3-O-glucosidePolyphenolsFlavonoidsAnthocyaninsShow Food Phytochemical
Procyanidin dimer A2PolyphenolsFlavonoidsFlavanolsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
(-)-EpicatechinPolyphenolsFlavonoidsFlavanolsShow Food Phytochemical
(+)-CatechinPolyphenolsFlavonoidsFlavanolsShow Food Phytochemical
QuercetinPolyphenolsFlavonoidsFlavonolsShow Food Phytochemical
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Black tea Flavan-3-olsPolyphenolsFlavonoidsFlavanolsShow Food Phytochemical
Green tea Flavan-3-olsPolyphenolsFlavonoidsFlavanolsShow Food Phytochemical
HydroxytyrosolPolyphenolsPhenolic acidsMiscellaneous phenolic acidsShow Food Phytochemical
Cocoa Flavan-3-olsPolyphenolsFlavonoidsFlavanolsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Phenols
Super-class
Benzenoids
Sub-class
1-hydroxy-2-unsubstituted benzenoids
Direct Parent Name
1-hydroxy-2-unsubstituted benzenoids
Alternative Parent Names
["Benzene and substituted derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides"]
External Descriptor Annotations
["monocarboxylic acid", "phenols"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound"]

Spectra from Online Resources

Record IDSourceDescriptionView
GLS00020MassBankEI-B Spectrum - -, unspecifiedView Spectra
JP003520MassBankEI-B Spectrum - -, [M]+*View Spectra
JP007234MassBankEI-B Spectrum - -, [M]+*View Spectra
JP011044MassBankEI-B Spectrum - -, [M]+*View Spectra
KO000968MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000969MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO000970MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO000971MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO000972MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
KZ000008MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
KZ000101MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
OUF00067MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR010008MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PS003201ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS003203ReSpectN/A Spectrum - 30, [M+H]+View Spectra

Food Sources

NameGroup
Olive, blackFruit, Drupes PublicationsShow
Olive, greenFruit, Drupes PublicationsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
QuercetinAcerolaFruit, Tropical fruits PublicationsShow
(-)-EpicatechinAlmondNuts PublicationsShow
Procyanidin dimer A2American cranberryFruit, Berries PublicationsShow
QuercetinAmerican cranberryFruit, Berries PublicationsShow
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
QuercetinAngelicaHerbs and Spices PublicationsShow
(-)-EpicatechinAppleFruit, Pomes PublicationsShow
(+)-CatechinAppleFruit, Pomes PublicationsShow
QuercetinAppleFruit, Pomes PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
(-)-EpicatechinApple ciderBeverages, Alcoholic PublicationsShow
(+)-CatechinApple ciderBeverages, Alcoholic PublicationsShow
(-)-EpicatechinApple juiceBeverages, Non-alcoholic PublicationsShow
(+)-CatechinApple juiceBeverages, Non-alcoholic PublicationsShow
QuercetinApple juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
(-)-EpicatechinApricotFruit, Drupes PublicationsShow
(+)-CatechinApricotFruit, Drupes PublicationsShow
(+)-CatechinBananaFruit, Tropical fruits PublicationsShow
(-)-EpicatechinBeerBeverages, Alcoholic PublicationsShow
(+)-CatechinBeerBeverages, Alcoholic PublicationsShow
Caffeic acidBeerBeverages, Alcoholic PublicationsShow
(-)-EpicatechinBlack teaTeas and herbal teas PublicationsShow
(+)-CatechinBlack teaTeas and herbal teas PublicationsShow
QuercetinBlack teaTeas and herbal teas PublicationsShow
Cyanidin 3-O-glucosideBlackberryFruit, Berries PublicationsShow
(-)-EpicatechinBlackberryFruit, Berries PublicationsShow
(+)-CatechinBlackberryFruit, Berries PublicationsShow
QuercetinBlackberryFruit, Berries PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideBlackcurrantFruit, Berries PublicationsShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
(-)-EpicatechinBroad beanPulses and beans PublicationsShow
(+)-CatechinBroad beanPulses and beans PublicationsShow
QuercetinBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
QuercetinCherry tomatoVegetables, Fruit vegetables PublicationsShow
(-)-EpicatechinChocolateCocoa and cocoa products PublicationsShow
(+)-CatechinChocolateCocoa and cocoa products PublicationsShow
(-)-EpicatechinCiderBeverages, Alcoholic PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
(-)-EpicatechinCocoaCocoa and cocoa products PublicationsShow
(+)-CatechinCocoaCocoa and cocoa products PublicationsShow
(-)-EpicatechinCocoa beanCocoa and cocoa products PublicationsShow
(+)-CatechinCocoa beanCocoa and cocoa products PublicationsShow
(-)-EpicatechinCocoa powderCocoa and cocoa products PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
(-)-EpicatechinCommon chokecherryFruit, Drupes PublicationsShow
(-)-EpicatechinCommon walnutNuts PublicationsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Caffeic acidEggplantVegetables, Fruit vegetables PublicationsShow
Cyanidin 3-O-glucosideElderberryFruit, Berries PublicationsShow
(-)-EpicatechinEuropean cranberryFruit, Berries PublicationsShow
QuercetinEuropean cranberryFruit, Berries PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideEuropean plumFruit, Drupes PublicationsShow
(-)-EpicatechinEuropean plumFruit, Drupes PublicationsShow
(+)-CatechinEuropean plumFruit, Drupes PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
(-)-EpicatechinGrapeFruit, Berries PublicationsShow
(-)-EpicatechinGreen teaTeas and herbal teasShow
(+)-CatechinGreen teaTeas and herbal teas PublicationsShow
QuercetinGreen teaTeas and herbal teas PublicationsShow
Cyanidin 3-O-glucosideLettuceVegetables, Leaf vegetables PublicationsShow
QuercetinLettuceVegetables, Leaf vegetables PublicationsShow
Procyanidin dimer A2LingonberryFruit, Berries PublicationsShow
Caffeic acidMateTeas and herbal teas PublicationsShow
Cyanidin 3-O-glucosideOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
HydroxytyrosolOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
HydroxytyrosolOlive, greenFruit, Drupes PublicationsShow
QuercetinOnionVegetables, Onion-family PublicationsShow
QuercetinOrange juiceBeverages, Non-alcoholic PublicationsShow
QuercetinParsnipVegetables, Root vegetables PublicationsShow
Cyanidin 3-O-glucosidePeachFruit, Drupes PublicationsShow
(-)-EpicatechinPeachFruit, Drupes PublicationsShow
(+)-CatechinPeachFruit, Drupes PublicationsShow
(-)-EpicatechinPearFruit, Pomes PublicationsShow
(+)-CatechinPearFruit, Pomes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
(+)-CatechinPecan nutNuts PublicationsShow
(-)-EpicatechinPomegranateFruit, Tropical fruits PublicationsShow
Cyanidin 3-O-glucosidePomegranate juiceBeverages, Non-alcoholic PublicationsShow
Cyanidin 3-O-glucosideRed raspberryFruit, Berries PublicationsShow
(+)-CatechinRed wineBeverages, Alcoholic PublicationsShow
Cyanidin 3-O-glucosideStrawberryFruit, Berries PublicationsShow
(-)-EpicatechinStrawberryFruit, Berries PublicationsShow
(+)-CatechinStrawberryFruit, Berries PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideSweet cherryFruit, Drupes PublicationsShow
(-)-EpicatechinSweet cherryFruit, Drupes PublicationsShow
(+)-CatechinSweet cherryFruit, Drupes PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
(-)-EpicatechinTeaTeas and herbal teas PublicationsShow
QuercetinTomatoVegetables, Fruit vegetables PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Cyanidin 3-O-glucoside 4'-Hydroxyphenylacetic acidhumanfeces, urineNot AvailableNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
Procyanidin dimer A2 4'-Hydroxyphenylacetic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
Orange flavanones 4'-Hydroxyphenylacetic acidhumanplasma, urine, urine (major)gut microbiota metabolite5h-8h50-200 nmol/L10-30%C8H8O3152.047344118 Detailed Intervention Studies Publications
(-)-Epicatechin 4'-Hydroxyphenylacetic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
(+)-Catechin 4'-Hydroxyphenylacetic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
Quercetin 4'-Hydroxyphenylacetic acidhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
Caffeic acid 4'-Hydroxyphenylacetic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
Black tea Flavan-3-ols 4'-Hydroxyphenylacetic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Detailed Intervention Studies
Green tea Flavan-3-ols 4'-Hydroxyphenylacetic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Detailed Intervention Studies
Hydroxytyrosol 4'-Hydroxyphenylacetic acidhumanplasmagut microbiota metaboliteNot Available5-20µmol/LNot AvailableC8H8O3152.047344118 Detailed Intervention Studies Publications
Cocoa Flavan-3-ols 4'-Hydroxyphenylacetic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C8H8O3152.047344118 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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