Record Information
Version1.0
Creation date2011-09-21 00:23:39 UTC
Update date2018-05-29 01:52:56 UTC
Primary IDFDB023037
Secondary Accession Numbers
  • FDB029822
Chemical Information
FooDB 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 species (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. [HMDB]
CAS Number3247-75-4
Structure
Thumb
Synonyms
SynonymSource
(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-(3-hydroxyphenyl)-3-hydroxypropanoatehmdb
3-(3-hydroxyphenyl)-3-hydroxypropanoic acidhmdb
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
Chemical FormulaC9H10O4
IUPAC name3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
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
Isomeric SMILESOC(CC(O)=O)C1=CC(O)=CC=C1
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Role

Indirect biological role:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash Key
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-1c85dbbfd5980c188548View in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-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 AvailableView in JSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
    ChemSpider ID93013
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound ID102959
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID959
    DrugBank IDNot Available
    HMDB IDHMDB02643
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference