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Showing metabocard for 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (HMDB02643)

Record Information
Version 3.5
Creation Date 2006-05-22 08:18:00 -0600
Update Date 2013-05-29 22:24:02 -0600
HMDB ID HMDB02643
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-(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 Link_out). 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 Link_out). 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3-Hydroxyphenyl)hydracrylate
  2. (3-Hydroxyphenyl)hydracrylic acid
  3. 3'-Hydroxyphenylhydracrylic acid
  4. 3-(3-Hydroxyphenyl)-3-hydroxypropanoate
  5. 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
  6. 3-(3-Hydroxyphenyl)-3-hydroxypropionate
  7. 3-(3-Hydroxyphenyl)-3-hydroxypropionic acid
  8. 3-(3-Hydroxyphenyl)hydracrylate
  9. 3-(3-Hydroxyphenyl)hydracrylic acid
  10. 3-(m-Hydroxyphenyl)hydracrylate
  11. 3-(m-Hydroxyphenyl)hydracrylic acid
  12. 3-Hydroxy-3-(3-hydroxyphenyl)propionic acid
  13. 3-Hydroxyphenyl-hydracrylic acid
  14. b-(m-Hydroxyphenyl)hydracrylate
  15. b-(m-Hydroxyphenyl)hydracrylic acid
  16. beta-(m-Hydroxyphenyl)hydracrylate
  17. beta-(m-Hydroxyphenyl)hydracrylic acid
  18. HPHPA
Chemical Formula C9H10O4
Average Molecular Weight 182.1733
Monoisotopic Molecular Weight 182.057908808
IUPAC Name 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
Traditional IUPAC Name 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
CAS Registry Number 3247-75-4
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 Key KHTAGVZHYUZYMF-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzyl Alcohols and Derivatives
Sub Class N/A
Other Descriptors
  • Organic Compounds
Substituents
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
Direct Parent Benzyl Alcohols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 6.31 g/L ALOGPS
LogP 0.68 ALOGPS
LogP 0.68 ChemAxon
LogS -1.46 ALOGPS
pKa (strongest acidic) 3.94 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 77.76 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 45.31 ChemAxon
Polarizability 17.31 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
Urine Detected and Quantified
5.9 (1.4-22.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Detected and Quantified
0.55-54.93 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Detected and Quantified
16 (0.8-83) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
91.5 +/- 90.4 umol/mmol creatinine Children (1-13 year old) Male Normal
Urine Detected and Quantified
85.5 +/- 55.9 umol/mmol creatinine Children (1-13 year old) Female Normal
Urine Detected and Quantified
39.8 +/- 50.2 umol/mmol creatinine Adult (>18 years old) Not Specified Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
0.3-12.7 umol/mmol creatinine Newborn (0-30 days old) Both Normal
Urine Detected and Quantified
4.2 (0.9-15.3) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Comment Hypertension (mild)
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Comment Hypertension (mild)
Urine Detected and Quantified 192.4 +/- 90.4 umol/mmol creatinine Children (1-13 year old) Male Autisme
Associated Disorders and Diseases
Disease References
Autism
  • 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. Pubmed: 20423563 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID 959 Link_out
    FoodDB ID FDB023037
    KNApSAcK ID Not Available
    Chemspider ID 93013 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB02643 Link_out
    Metagene Link HMDB02643 Link_out
    METLIN ID 6729 Link_out
    PubChem Compound 102959 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not 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 Link_out
    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. Pubmed: 20423563 Link_out