Human Metabolome Database Version 3.5

Showing metabocard for 3-(3-Hydroxyphenyl)propanoic acid (HMDB00375)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:26:06 -0600
HMDB ID HMDB00375
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-(3-Hydroxyphenyl)propanoic acid
Description 3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID 15479001 Link_out) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID 12663291 Link_out). 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 Link_out, 12663291 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H10O3
Average Molecular Weight 166.1739
Monoisotopic Molecular Weight 166.062994186
IUPAC Name 3-(3-hydroxyphenyl)propanoic acid
Traditional IUPAC Name dihydro-3-coumaric acid
CAS Registry Number 621-54-5
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 Key QVWAEZJXDYOKEH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • monocarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Phenols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • 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 2.8 g/L ALOGPS
LogP 1.14 ALOGPS
LogP 1.75 ChemAxon
LogS -1.77 ALOGPS
pKa (strongest acidic) 4.21 ChemAxon
pKa (strongest basic) -6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 43.95 ChemAxon
Polarizability 16.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS 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
  • Not Applicable
Blood Detected and Quantified
0.056 +/- 0.015 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.035 +/- 0.008 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.086 +/- 0.021 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.084 +/- 0.022 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.04 +/- 0.008 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.039 +/- 0.012 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.034 +/- 0.01 uM Adult (>18 years old) Male Comment Normal
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
Blood Detected and Quantified
0.775 +/- 0.747 uM Adult (>18 years old) Male Comment Normal
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
Urine Detected and Quantified
0.32 (0.2 - 0.5) umol/mmol creatinine Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
1.5 +/- 0.46 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 961
  • Not Applicable
Urine Detected and Quantified
0.043 +/- 0.006 umol/mmol creatinine Adult (>18 years old) Male Comment 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)
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID 961 Link_out
FoodDB ID FDB021993
KNApSAcK ID Not Available
Chemspider ID 89 Link_out
KEGG Compound ID C11457 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00375 Link_out
Metagene Link HMDB00375 Link_out
METLIN ID 5364 Link_out
PubChem Compound 91 Link_out
PDB ID Not Available
ChEBI ID 1427 Link_out
References
Synthesis Reference Dombrow, 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 Link_out
  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 Link_out
  3. 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 Link_out
  4. 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 Link_out