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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-12-01 23:05:55 UTC
HMDB IDHMDB00375
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-(3-Hydroxyphenyl)propanoic acid
Description3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID 15479001 ) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID 12663291 ). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID 15479001 , 12663291 ).
Structure
Thumb
Synonyms
  1. 3-(3-Hydroxy-phenyl)-propanoate
  2. 3-(3-Hydroxy-phenyl)-propanoic acid
  3. 3-(3-Hydroxy-phenyl)-propionic acid
  4. 3-(3-Hydroxyphenyl)propanoate
  5. 3-(3-Hydroxyphenyl)propanoic acid
  6. 3-(3-Hydroxyphenyl)propionate
  7. 3-(3-Hydroxyphenyl)propionic acid
  8. 3-(m-Hydroxyphenyl)propionate
  9. 3-(m-Hydroxyphenyl)propionic acid
  10. 3-Hydroxybenzenepropanoate
  11. 3-Hydroxybenzenepropanoic acid
  12. 3-Hydroxydihydrocinnamate
  13. 3-Hydroxydihydrocinnamic acid
  14. 3-Hydroxyhydrocinnamic acid
  15. 3-Hydroxyphenylpropanoate
  16. 3-Hydroxyphenylpropanoic acid
  17. 3-Hydroxyphenylpropionate
  18. 3-Hydroxyphenylpropionic acid
  19. b-(3-Hydroxyphenyl)propionate
  20. b-(3-Hydroxyphenyl)propionic acid
  21. b-(m-Hydroxyphenyl)propionate
  22. b-(m-Hydroxyphenyl)propionic acid
  23. beta-(3-Hydroxyphenyl)propionate
  24. beta-(3-Hydroxyphenyl)propionic acid
  25. beta-(m-Hydroxyphenyl)propionate
  26. beta-(m-Hydroxyphenyl)propionic acid
  27. Dihydro-3-coumaric acid
  28. Dihydro-m-coumarate
  29. Dihydro-m-coumaric acid
  30. m-Hydrocoumaric acid
  31. m-Hydroxy-Hydrocinnamate
  32. m-Hydroxy-Hydrocinnamic acid
  33. m-Hydroxyphenylpropionate
  34. m-Hydroxyphenylpropionic acid
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(3-hydroxyphenyl)propanoic acid
Traditional Namedihydro-3-coumaric acid
CAS Registry Number621-54-5
SMILES
OC(=O)CCC1=CC=CC(O)=C1
InChI Identifier
InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)
InChI KeyQVWAEZJXDYOKEH-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassN/A
Other Descriptors
  • Organic Compounds
  • monocarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct ParentPhenols and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • 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 Solubility2.8ALOGPS
logP1.14ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m3·mol-1ChemAxon
Polarizability16.92 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
BloodDetected and Quantified0.056 +/- 0.015 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.035 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.086 +/- 0.021 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.084 +/- 0.022 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.04 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.039 +/- 0.012 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.034 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
details
BloodDetected and Quantified0.775 +/- 0.747 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
details
FecesDetected and Quantified74.0188 +/- 139.0110 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified105.913 +/- 182.941 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified288.854 +/- 717.321 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified290.659 +/- 834.0660 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.32 (0.2 - 0.5) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.5 +/- 0.46 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
details
UrineDetected and Quantified0.043 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
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
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID961
FoodDB IDFDB021993
KNApSAcK IDNot Available
Chemspider ID89
KEGG Compound IDC11457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00375
Metagene LinkHMDB00375
METLIN ID5364
PubChem Compound91
PDB IDNot Available
ChEBI ID1427
References
Synthesis ReferenceDombrow, M.; Linnell, W. H. Preparation of m-hydroxyphenylpropionic acid. Journal of Pharmacy and Pharmacology (1952), 4 118-19.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. Pubmed: 10706426
  2. Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. Pubmed: 2044590
  3. Rios LY, Gonthier MP, Remesy C, Mila I, Lapierre C, Lazarus SA, Williamson G, Scalbert A: Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects. Am J Clin Nutr. 2003 Apr;77(4):912-8. Pubmed: 12663291
  4. Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24. Pubmed: 15479001