Showing Compound Card for p-Hydroxyphenylacetic acid (CDB006336)

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Record Information
Version1.0
Created at2020-09-11 15:49:32 UTC
Updated at2022-12-13 23:36:27 UTC
CannabisDB IDCDB006336
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namep-Hydroxyphenylacetic acid
Descriptionp-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate or 4-carboxymethylphenol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). p-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to humans. p-hydroxyphenylacetic acid can be biosynthesized from homovanillin; which is catalyzed by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. In humans, p-hydroxyphenylacetic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, p-Hydroxyphenylacetic acid is found, on average, in the highest concentration within a few different foods, such as olives, american cranberries, and grape wines and in a lower concentration in corns, beers, and oats. p-Hydroxyphenylacetic acid has also been detected, but not quantified in, several different foods, such as common wheats, herbs and spices, cocoa beans, dandelions, and evening primroses. This could make p-hydroxyphenylacetic acid a potential biomarker for the consumption of these foods. p-Hydroxyphenylacetic acid is a potentially toxic compound. p-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, perillyl alcohol administration for cancer treatment, crohn's disease, and ulcerative colitis; p-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(p-Hydroxyphenyl)acetic acidChEBI
4-CarboxymethylphenolChEBI
4-Hydroxybenzeneacetic acidChEBI
4-HydroxyphenylacetateChEBI
4-Hydroxyphenylacetic acidKegg
(p-Hydroxyphenyl)acetateGenerator
4-HydroxybenzeneacetateGenerator
p-HydroxyphenylacetateGenerator
(4-Hydroxy-phenyl)-acetateHMDB
(4-Hydroxy-phenyl)-acetic acidHMDB
(4-Hydroxy-phenyl)-essigsaeureHMDB
(4-Hydroxyphenyl)acetateHMDB
(4-Hydroxyphenyl)acetic acidHMDB
(p-Hydroxyphenyl)-acetateHMDB
(p-Hydroxyphenyl)-acetic acidHMDB
4-Hydroxy-benzeneacetateHMDB
4-Hydroxy-benzeneacetic acidHMDB
4-Hydroxyphenyl-acetic acidHMDB
Parahydroxy phenylacetateHMDB
Parahydroxy phenylacetic acidHMDB
ParahydroxyphenylacetateHMDB
Para-hydroxyphenylacetic acidHMDB
p-Hydroxyphenylacetic acidChEBI
4'-Hydroxyphenylacetic acidHMDB
2-(4-Hydroxyphenyl)acetic acidHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxyphenylacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyXQXPVVBIMDBYFF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.93ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee12014-09-20View Spectrum
GC-MSp-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrumsplash10-01ta-1930000000-57c9e8ddaa10569055aaSpectrum
GC-MSp-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrumsplash10-0h01-0940000000-a14203384331e709252fSpectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-03fs-1930000000-80c21819072fb01958dcSpectrum
GC-MSp-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrumsplash10-00di-9410000000-678591f03aba45c2a6aeSpectrum
GC-MSp-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrumsplash10-0h0r-2940000000-760b6c506072a61059c0Spectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-2900000000-3939c62b0d7f649ff402Spectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-fdb73325a31c758496e9Spectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0gyk-0980000000-ed36f36969e4d51b9a8dSpectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-01ta-1930000000-57c9e8ddaa10569055aaSpectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0h01-0940000000-a14203384331e709252fSpectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-03fs-1930000000-80c21819072fb01958dcSpectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9410000000-678591f03aba45c2a6aeSpectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0h0r-2940000000-760b6c506072a61059c0Spectrum
GC-MSp-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-03fs-1931100000-50456fed0c5ef95ecb57Spectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-4900000000-b6f6363476ffa290862fSpectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-5930000000-abf5245dd22d012d04f8Spectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSp-Hydroxyphenylacetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-0900000000-e3dfb4b180d858b3a8542012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-056r-9400000000-9a6cb39e019a0b40a6662012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0kdl-9400000000-35ecc22161defddc7b212012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0a4i-2900000000-3939c62b0d7f649ff4022012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0a4i-6900000000-fdb73325a31c758496e92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-4900000000-88da569804a98e1a99ea2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-0a95379b7cea57386b0b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-88da569804a98e1a99ea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-0a95379b7cea57386b0b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-02cd23fa5ff37594d2be2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-bbac468eb7ce6ea991232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-05d18e7bb4163e35e2aa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-9a0086561d6f8a1696702017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-398dff08b5b2a56e658c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-5f75ea6de2d6bad624d82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-7ce02fea5a9ef38024f22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0900000000-12e388b0927ed1c6e1662016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2900000000-ae1870eee4853c57a4472016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00183 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00241 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00279 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.00195 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00128 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00127 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000020
DrugBank IDNot Available
Phenol Explorer Compound ID573
FoodDB IDFDB010534
KNApSAcK IDNot Available
Chemspider ID124
KEGG Compound IDC00642
BioCyc ID4-HYDROXYPHENYLACETATE
BiGG ID35599
Wikipedia Link4-hydroxyphenylacetic_acid
METLIN ID130
PubChem Compound127
PDB IDNot Available
ChEBI ID18101
References
General ReferencesNot Available