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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:22:27 UTC
HMDB IDHMDB0000375
Secondary Accession Numbers
  • HMDB00375
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
ValueSource
3-(3-Hydroxy-phenyl)-propanoic acidChEBI
3-(3-Hydroxyphenyl)propionic acidChEBI
3-(m-Hydroxyphenyl)propionic acidChEBI
beta-(m-Hydroxyphenyl)propionic acidChEBI
dihydro-3-Coumaric acidChEBI
3-(3-Hydroxy-phenyl)-propanoateGenerator
3-(3-Hydroxyphenyl)propanoateGenerator
3-(3-Hydroxyphenyl)propionateGenerator
3-(m-Hydroxyphenyl)propionateGenerator
b-(m-Hydroxyphenyl)propionateGenerator
b-(m-Hydroxyphenyl)propionic acidGenerator
beta-(m-Hydroxyphenyl)propionateGenerator
β-(m-hydroxyphenyl)propionateGenerator
β-(m-hydroxyphenyl)propionic acidGenerator
dihydro-3-CoumarateGenerator
3-(3-Hydroxy-phenyl)-propionic acidHMDB
3-HydroxybenzenepropanoateHMDB
3-Hydroxybenzenepropanoic acidHMDB
3-HydroxydihydrocinnamateHMDB
3-Hydroxydihydrocinnamic acidHMDB
3-Hydroxyhydrocinnamic acidHMDB
3-HydroxyphenylpropanoateHMDB
3-Hydroxyphenylpropanoic acidHMDB
3-HydroxyphenylpropionateHMDB
3-Hydroxyphenylpropionic acidHMDB
b-(3-Hydroxyphenyl)propionateHMDB
b-(3-Hydroxyphenyl)propionic acidHMDB
beta-(3-Hydroxyphenyl)propionateHMDB
beta-(3-Hydroxyphenyl)propionic acidHMDB
dihydro-m-CoumarateHMDB
dihydro-m-Coumaric acidHMDB
m-Hydrocoumaric acidHMDB
m-Hydroxy-hydrocinnamateHMDB
m-Hydroxy-hydrocinnamic acidHMDB
m-HydroxyphenylpropionateHMDB
m-Hydroxyphenylpropionic acidHMDB
dihydro-3-Coumaric acid, monosodium saltMeSH
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(3-hydroxyphenyl)propanoic acid
Traditional Name3-hydroxyphenylpropionic 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
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
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

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 Solubility2.8 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability16.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-1900000000-77779ae60312f591e17eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-0930000000-cb674deffe8e93afca7eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-3900000000-df46f44d343adb6bf4beView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-4030a1092b3837900ee3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-4a45085593200cc6c7d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-ac287061b5cdcc1f846bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9400000000-1e275b3ba45b8048aa13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ec17e3f1692cb9469bebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0900000000-4407c82bb7a72d9feb58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r5-4900000000-2b7cd80f8f959113fe79View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    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 Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
    BloodDetected and Quantified0.775 +/- 0.747 uMAdult (>18 years old)Male
    Normal
    details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 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 Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal 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 Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
    UrineDetected and Quantified0.043 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not Quantified Adult (>18 years old)Not Specifiedasymptomatic diverticulosis details
    FecesDetected but not Quantified Adult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
    UrineDetected and Quantified2.292 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified1.325 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • 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
    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
    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 ]

    Enzymes

    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)propanoic acid → 6-[3-(2-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    3-(3-Hydroxyphenyl)propanoic acid → 3,4,5-trihydroxy-6-{[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)propanoic acid → 3-[3-(Sulfooxy)phenyl]propanoic aciddetails