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Record Information
Version3.6
Creation Date2006-05-22 14:18:00 UTC
Update Date2016-02-11 01:05:44 UTC
HMDB IDHMDB02643
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
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 (PMID:11978597 ). 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. (PMID:20423563 ). 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.
Structure
Thumb
Synonyms
ValueSource
(3-Hydroxyphenyl)hydracrylateHMDB
(3-Hydroxyphenyl)hydracrylic acidHMDB
3'-Hydroxyphenylhydracrylic acidHMDB
3-(3-Hydroxyphenyl)-3-hydroxypropanoateHMDB
3-(3-Hydroxyphenyl)-3-hydroxypropionateHMDB
3-(3-Hydroxyphenyl)-3-hydroxypropionic acidHMDB
3-(3-Hydroxyphenyl)hydracrylateHMDB
3-(3-Hydroxyphenyl)hydracrylic acidHMDB
3-(m-Hydroxyphenyl)hydracrylateHMDB
3-(m-Hydroxyphenyl)hydracrylic acidHMDB
3-Hydroxy-3-(3-hydroxyphenyl)propionic acidHMDB
3-Hydroxyphenyl-hydracrylic acidHMDB
b-(m-Hydroxyphenyl)hydracrylateHMDB
b-(m-Hydroxyphenyl)hydracrylic acidHMDB
beta-(m-Hydroxyphenyl)hydracrylateHMDB
beta-(m-Hydroxyphenyl)hydracrylic acidHMDB
HPHPAHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
Traditional Namemhpha
CAS Registry Number3247-75-4
SMILES
OC(CC(O)=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=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 KeyInChIKey=KHTAGVZHYUZYMF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
  • Phenol
  • Beta-hydroxy acid
  • Benzenoid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.31 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.31 m3·mol-1ChemAxon
Polarizability17.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified5.9 (1.4-22.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified69.556 +/- 56.735 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified5.121 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.55-54.93 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified16 (0.8-83) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified91.5 +/- 90.4 umol/mmol creatinineChildren (1-13 years old)MaleNormal details
UrineDetected and Quantified85.5 +/- 55.9 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
UrineDetected and Quantified39.8 +/- 50.2 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.3-12.7 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified4.2 (0.9-15.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified57.84 +/- 80.919 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified16.197 +/- 9.854 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.326 +/- 2.352 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected and Quantified192.4 +/- 90.4 umol/mmol creatinineChildren (1-13 years old)MaleAutism details
Associated Disorders and Diseases
Disease References
Autism
  1. 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. [20423563 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID959
FoodDB IDFDB023037
KNApSAcK IDNot Available
Chemspider ID93013
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02643
Metagene LinkHMDB02643
METLIN ID6729
PubChem Compound102959
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [11978597 ]
  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. [20423563 ]