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Record Information
Version1.0
Creation Date2014-10-02 19:01:15 UTC
Update Date2016-11-09 01:09:15 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
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(3-Hydroxyphenyl)hydracrylic acidChEBI
3'-Hydroxyphenylhydracrylic acidChEBI
3-(3-Hydroxyphenyl)-3-hydroxypropionic acidChEBI
3-(3-Hydroxyphenyl)hydracrylic acidChEBI
3-(m-Hydroxyphenyl)hydracrylic acidChEBI
3-Hydroxy-3-(3-hydroxyphenyl)propionic 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 acid
3-(3'-Hydroxyphenyl)hydracrylic acid
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid
3-Hydroxy-3-(3'-hydroxyphenyl)propionic acid
beta, m-Dihydroxyphenylpropionic acid
beta, meta-Dihydroxyphenylpropionic acid
m-Hydroxyphenylhydracrylic acid
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-00di-6900000000-1c85dbbfd5980c188548View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS)splash10-014i-3094000000-b60bebf30bd58b1783a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-db4168cb272b787d7521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-1900000000-bf141ae9daa7c4c192b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-6900000000-6baa657777aef17afbb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-9e5b5607972b5e60f0ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07ci-3900000000-d464d54fbcadeb4e4444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-4de7b48574933f1a2830View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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
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.