Record Information
Version1.0
Creation date2011-09-21 00:06:40 UTC
Update date2015-10-09 22:33:34 UTC
Primary IDFDB021993
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). [HMDB]
CAS Number621-54-5
Structure
Thumb
Synonyms
SynonymSource
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-HydroxyphenylpropanoateKegg
3-(3-Hydroxyphenyl)propanoateKegg
3-(3-Hydroxy-phenyl)-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-Hydroxyphenylpropanoic acidGenerator
3-(3-Hydroxy-phenyl)-propionic acidHMDB
3-HydroxybenzenepropanoateHMDB
3-Hydroxybenzenepropanoic acidHMDB
3-HydroxydihydrocinnamateHMDB
3-Hydroxydihydrocinnamic acidHMDB
3-Hydroxyhydrocinnamic 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 saltHMDB
3-(3'-Hydroxyphenyl)propanoic acidNot Available
3-Hydroxy-dihydrocinnamic acidNot Available
m-Hydroxy-dihydrocinnamic acidNot Available
3-(3-Hydroxyphenyl)propanoic acidhmdb
dihydro-3-CoumarateGenerator
dihydro-3-Coumaric acidChEBI
m-hydroxy-Hydrocinnamatehmdb
m-hydroxy-Hydrocinnamic acidhmdb
β-(m-hydroxyphenyl)propionateGenerator
β-(m-hydroxyphenyl)propionic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H10O3
IUPAC name3-(3-hydroxyphenyl)propanoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)CCC1=CC=CC(O)=C1
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
Classification
Description belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
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

Source:

Biological location:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-1900000000-77779ae60312f591e17eJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-0930000000-cb674deffe8e93afca7eJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-1900000000-77779ae60312f591e17eJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-0930000000-cb674deffe8e93afca7eJSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-3900000000-df46f44d343adb6bf4beJSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-4030a1092b3837900ee3JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-4a45085593200cc6c7d3JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-ac287061b5cdcc1f846bJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9400000000-1e275b3ba45b8048aa13JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ec17e3f1692cb9469bebJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0900000000-4407c82bb7a72d9feb58JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r5-4900000000-2b7cd80f8f959113fe79JSpectraViewer
    ChemSpider ID89
    ChEMBL IDCHEMBL134401
    KEGG Compound IDC11457
    Pubchem Compound ID91
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID961
    DrugBank IDNot Available
    HMDB IDHMDB00375
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID961
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference