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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:18:00 UTC
Update Date2017-10-23 19:04:00 UTC
HMDB IDHMDB0002643
Secondary Accession Numbers
  • HMDB02643
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)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-(3-Hydroxyphenyl)-3-hydroxypropanoateGenerator
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
beta-(Meta-hydroxyphenyl)hydracrylic acidMeSH
HPHPA CPDMeSH
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 KeyKHTAGVZHYUZYMF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassPhenylpropanoic acids
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
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physiological effect

Health effect:

  Health condition:

Role

Indirect biological role:

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 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-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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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 Quantified Adult (>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 Quantified Adult (>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 Quantified Adult (>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 Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>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. doi: 10.1179/147683010X12611460763968. [PubMed: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
    METLIN ID6729
    PubChem Compound102959
    PDB IDNot Available
    ChEBI ID86369
    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. [PubMed: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. doi: 10.1179/147683010X12611460763968. [PubMed:20423563 ]

    Enzymes

    General function:
    Involved in sulfotransferase activity
    Specific function:
    Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
    Gene Name:
    SULT2B1
    Uniprot ID:
    O00204
    Molecular weight:
    39598.595
    Reactions
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid → 3-(3-hydroxyphenyl)-3-(sulfooxy)propanoic aciddetails
    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
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid → 6-[3-(2-carboxy-1-hydroxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid → 3,4,5-trihydroxy-6-{[3-hydroxy-3-(3-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
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid → 3-hydroxy-3-[3-(sulfooxy)phenyl]propanoic aciddetails