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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-12 03:36:10 UTC
Update Date2019-07-23 06:34:50 UTC
HMDB IDHMDB0041683
Secondary Accession Numbers
  • HMDB41683
Metabolite Identification
Common Name4-Hydroxyphenyl-2-propionic acid
Description4-Hydroxyphenyl-2-propionic acid belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 4-Hydroxyphenyl-2-propionic acid has been detected in multiple biofluids, such as urine and blood (PMID: 20428313 ). Within the cell, 4-hydroxyphenyl-2-propionic acid is primarily located in the cytoplasm.
Structure
Data?1563863690
Synonyms
ValueSource
4-Hydroxyphenyl-2-propionateGenerator
2-HPPA CPDHMDB
2-(4-Hydroxyphenyl)propionic acidHMDB
4-Hydroxy-α-methylbenzeneacetic acidCAS
2-(4-Hydroxyphenyl)propanoic acidCAS
2-(p-Hydroxyphenyl)-propionic acidCAS
Methyl 4-hydroxyphenylacetic acidCAS
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-(4-hydroxyphenyl)propanoic acid
Traditional Name4-hydroxyhydratropate
CAS Registry Number938-96-5
SMILES
CC(C(O)=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-6,10H,1H3,(H,11,12)
InChI KeyZHMMPVANGNPCBW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 2-phenylpropanoic-acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 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
Disposition

Source:

Biological location:

Role

Biological role:

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
Water Solubility2.84 g/LALOGPS
logP1.52ALOGPS
logP1.85ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.92 m³·mol⁻¹ChemAxon
Polarizability16.77 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-e57ad67ceeefc0162be2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g3-9640000000-3de19c58f9e40303ed0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-0d1c1fd48877d2f30057JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-2900000000-0e20fe3cb14a45fb328fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-4900000000-9945b825ae4cd1e9e158JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9700000000-b25269bd8454951950fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-7284c76e93a8edba4eaeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-234abc35f0b9f45adbd2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-a44e00b2e6f6e3490e2eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fxy-9700000000-0a97f98fd80379ea6898JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-3de25720a4f194f0da7dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0900000000-f5c493ba5fa35fca91a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9400000000-47e0704f057baaa82a6aJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.266 +/- 0.106 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.094 +/- 0.021 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.168 +/- 0.038 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.246 +/- 0.071 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.094 +/- 0.011 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.087 +/- 0.015 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.192 +/- 0.108 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.393 +/- 0.339 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.466 +/- 0.116 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029844
KNApSAcK IDNot Available
Chemspider ID92601
KEGG Compound IDC03080
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102526
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Hydroxyphenyl-2-propionic acid → 6-[4-(1-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4-Hydroxyphenyl-2-propionic acid → 3,4,5-trihydroxy-6-{[2-(4-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Hydroxyphenyl-2-propionic acid → 2-[4-(sulfooxy)phenyl]propanoic aciddetails