Record Information
Version2.0
Creation Date2012-05-31 14:04:26 -0600
Update Date2015-06-03 15:54:43 -0600
Secondary Accession Numbers
  • ECMDB04083
Identification
Name:3-(3-Hydroxyphenyl)propionate
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:
  • -(3-Hydroxyphenyl)propionate
  • -(3-Hydroxyphenyl)propionic acid
  • -(m-hydroxyphenyl)propionate
  • -(m-hydroxyphenyl)propionic acid
  • 3-(3-Hydroxy-phenyl)-propanoate
  • 3-(3-Hydroxy-phenyl)-propanoic acid
  • 3-(3-Hydroxy-phenyl)-propionate
  • 3-(3-hydroxy-phenyl)-propionic acid
  • 3-(3-Hydroxyphenyl)propanoate
  • 3-(3-Hydroxyphenyl)propanoic acid
  • 3-(3-Hydroxyphenyl)propionic acid
  • 3-(m-Hydroxyphenyl)propionate
  • 3-(m-Hydroxyphenyl)propionic acid
  • 3-Hydroxy-Benzenepropanoate
  • 3-Hydroxy-Benzenepropanoic acid
  • 3-Hydroxybenzenepropanoate
  • 3-Hydroxybenzenepropanoic acid
  • 3-Hydroxydihydrocinnamate
  • 3-Hydroxydihydrocinnamic acid
  • 3-Hydroxyhydrocinnamate
  • 3-hydroxyhydrocinnamic acid
  • 3-Hydroxyphenylpropanoate
  • 3-Hydroxyphenylpropanoic acid
  • 3-Hydroxyphenylpropionate
  • 3-Hydroxyphenylpropionic acid
  • 3HPP
  • B-(3-Hydroxyphenyl)propionate
  • B-(3-Hydroxyphenyl)propionic acid
  • B-(m-Hydroxyphenyl)propionate
  • B-(m-Hydroxyphenyl)propionic acid
  • Beta-(3-Hydroxyphenyl)propionate
  • Beta-(3-Hydroxyphenyl)propionic acid
  • Beta-(m-Hydroxyphenyl)propionate
  • Beta-(m-Hydroxyphenyl)propionic acid
  • Dihydro-3-coumarate
  • Dihydro-3-coumaric acid
  • Dihydro-m-coumarate
  • Dihydro-m-coumaric acid
  • m-Hydrocoumarate
  • M-hydrocoumaric acid
  • M-Hydroxy-hydrocinnamate
  • M-Hydroxy-Hydrocinnamic acid
  • M-Hydroxyphenylpropionate
  • M-Hydroxyphenylpropionic acid
  • MHP
  • β-(3-Hydroxyphenyl)propionate
  • β-(3-Hydroxyphenyl)propionic acid
  • β-(m-Hydroxyphenyl)propionate
  • β-(m-Hydroxyphenyl)propionic acid
Chemical Formula:C9H9O3
Weight:Average: 165.166
Monoisotopic: 165.055169154
InChI Key:QVWAEZJXDYOKEH-UHFFFAOYSA-M
InChI: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)/p-1
CAS number:621-54-5
IUPAC Name:3-(2-carboxyethyl)benzen-1-olate
Traditional IUPAC Name:3-(2-carboxyethyl)benzenolate
SMILES:OC(=O)CCC1=CC([O-])=CC=C1
Chemical Taxonomy
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
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic anion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.76 g/LALOGPS
logP1.03ALOGPS
logP1.75ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.5 m³·mol⁻¹ChemAxon
Polarizability16.53 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Phenylalanine metabolism ec00360
EcoCyc Pathways:
  • 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-d26c3b21f7020312d40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0900000000-699c005a1bb725fd53a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rb-9800000000-7bcd8a78529b98480a7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-50a324a9dcee74d98a37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2900000000-110fb0abad22d5d439caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-e365f28cb5fef822535dView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Konishi, Y., Kobayashi, S. (2004). "Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers." J Agric Food Chem 52:6418-6424. Pubmed: 15479001
  • Rios, L. Y., Gonthier, M. P., Remesy, C., Mila, I., Lapierre, C., Lazarus, S. A., Williamson, G., Scalbert, A. (2003). "Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects." Am J Clin Nutr 77:912-918. Pubmed: 12663291
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID1427
HMDB IDHMDB00375
Pubchem Compound ID6931501
Kegg IDC11457
ChemSpider ID5305660
Wikipedia IDNot Available
BioCyc ID3-HYDROXYPHENYL-PROPIONATE
EcoCyc ID3-HYDROXYPHENYL-PROPIONATE

Enzymes

General function:
Involved in 3-(3-hydroxyphenyl)propionate hydroxylase activity
Specific function:
Catalyzes the insertion of one atom of molecular oxygen into position 2 of the phenyl ring of 3-(3- hydroxyphenyl)propionate (3-HPP) and hydroxycinnamic acid (3HCI)
Gene Name:
mhpA
Uniprot ID:
P77397
Molecular weight:
62185
Reactions
3-(3-hydroxyphenyl)propanoate + NADH + O(2) = 3-(2,3-dihydroxyphenyl)propanoate + H(2)O + NAD(+).
(2E)-3-(3-hydroxyphenyl)prop-2-enoate + NADH + O(2) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + H(2)O + NAD(+).

Transporters

General function:
Involved in transmembrane transport
Specific function:
Could be a transporter for 3-phenylpropionate (hydrocinnamic acid)
Gene Name:
mhpT
Uniprot ID:
P77589
Molecular weight:
41550