3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (CHEM003922)

Record Information
Version1.0
Creation Date2014-10-02 19:01:15 UTC
Update Date2026-04-05 15:18:37 UTC
Accession NumberCHEM003922
Identification
Common Name3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
ClassSmall Molecule
Description
(3-Hydroxyphenyl)hydracrylate (HPHPA) is an organic acid detected in human urine. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (1). Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida sp. (2). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Human Neurotoxin
  • Metabolite
  • Natural Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3-Hydroxyphenyl)hydracrylic acidChEBI
3'-Hydroxyphenylhydracrylic acidChEBI
3-(m-Hydroxyphenyl)hydracrylic acidChEBI
3-Hydroxyphenyl-hydracrylic acidChEBI
b-(m-Hydroxyphenyl)hydracrylic acidChEBI
beta-(m-Hydroxyphenyl)hydracrylic acidChEBI
HPHPAChEBI
(3-Hydroxyphenyl)hydracrylateGenerator
3'-HydroxyphenylhydracrylateGenerator
3-(3-Hydroxyphenyl)-3-hydroxypropionateGenerator
3-(3-Hydroxyphenyl)hydracrylateGenerator
3-(m-Hydroxyphenyl)hydracrylateGenerator
3-Hydroxy-3-(3-hydroxyphenyl)propionateGenerator
3-Hydroxyphenyl-hydracrylateGenerator
b-(m-Hydroxyphenyl)hydracrylateGenerator
beta-(m-Hydroxyphenyl)hydracrylateGenerator
Β-(m-hydroxyphenyl)hydracrylateGenerator
Β-(m-hydroxyphenyl)hydracrylic acidGenerator
3-(3-Hydroxyphenyl)-3-hydroxypropanoateGenerator
HPHPA CPDHMDB
beta-(Meta-hydroxyphenyl)hydracrylic acidHMDB
MHPHAHMDB
3-Hydroxy-3-(3'-hydroxyphenyl)propanoic acidHMDB
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Mass182.173 g/mol
Monoisotopic Mass182.058 g/mol
CAS Registry Number3247-75-4
IUPAC Name3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
Traditional Namemhpha
SMILESOC(CC(O)=O)C1=CC(O)=CC=C1
InChI IdentifierInChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyKHTAGVZHYUZYMF-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
  • 3-phenylpropanoic-acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.31 g/LALOGPS
logP0.68ALOGPS
logP0.68ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.31 m³·mol⁻¹ChemAxon
Polarizability17.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsChronically high levels of HPHPA is associated with autism and schizophrenia.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0002643
FooDB IDFDB023037
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6729
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID93013
ChEBI ID86369
PubChem Compound ID102959
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17.
2. Shaw W: Increased urinary excretion of a 3-(3-hydroxyphenyl)-3-hydroxypropionic acid (HPHPA), an abnormal phenylalanine metabolite of Clostridia spp. in the gastrointestinal tract, in urine samples from patients with autism and schizophrenia. Nutr Neurosci. 2010 Jun;13(3):135-43. doi: 10.1179/147683010X12611460763968.
3. Kesli R, Gokcen C, Bulug U, Terzi Y: Investigation of the relation between anaerobic bacteria genus clostridium and late-onset autism etiology in children. J Immunoassay Immunochem. 2014;35(1):101-9. doi: 10.1080/15321819.2013.792834.