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3-(3-Hydroxyphenyl)propanoic acid (M2MDB000133)

Record Information
Version2.0
Creation Date2012-05-31 10:26:28 -0600
Update Date2015-09-13 12:56:08 -0600
Secondary Accession Numbers
  • ECMDB00375
Identification
Name:3-(3-Hydroxyphenyl)propanoic acid
Description3-(3-hydroxyphenyl)propanoic acid is a member of the chemical class known as Phenols and Derivatives. Phenols are compounds containing a phenol moiety, which is a benzene bearing an hydroxyl group. 3-(3-hydroxyphenyl)propanoic acid is an intermediate in phenylalanine metabolism pathways. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 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)propionate
  • 3-(3-Hydroxyphenyl)propionic acid
  • 3-(m-Hydroxyphenyl)propionate
  • 3-(m-Hydroxyphenyl)propionic 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
  • 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
  • β-(3-Hydroxyphenyl)propionate
  • β-(3-Hydroxyphenyl)propionic acid
  • β-(m-Hydroxyphenyl)propionate
  • β-(m-Hydroxyphenyl)propionic acid
Chemical Formula:C9H10O3
Weight:Average: 166.1739
Monoisotopic: 166.062994186
InChI Key:QVWAEZJXDYOKEH-UHFFFAOYSA-N
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)
CAS number:621-54-5
IUPAC Name:3-(3-hydroxyphenyl)propanoic acid
Traditional IUPAC Name:3-hydroxyphenylpropionic acid
SMILES:OC(=O)CCC1=CC=CC(O)=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
  • 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
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:1.362PhysProp
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD
3-(3-Hydroxyphenyl)propanoic acid + Oxygen + NADH + Hydrogen ion <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD
3-(3-Hydroxyphenyl)propanoic acid + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propanoate + Water + NAD
3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-Dihydroxycinnamate
SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 ThumbThumb?image type=greyscaleThumb?image type=simple
2-Oxopent-4-enoate metabolism 2PW002035 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Phenylalanine metabolism ec00360
EcoCyc Pathways:Not Available
Concentrations
Not Available
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
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-0ef65243a7fdde063c52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0avi-0900000000-f9b9f6b52e9e50218f53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0avi-0900000000-de2d8585bc952e840460View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0aor-3900000000-a0c560a0e53e97f29b2bView 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-0d7421595c1a4fe8a25eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-efb21a9dd58f39dfcf57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9300000000-258065f574b3915c0ac3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xs-0900000000-3e37174dd2fc252c5cd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-d6e289e9f660ec643659View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-8e0c82231fc0135fc3ccView 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:
  • 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
  • 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
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID1427
HMDB IDHMDB00375
Pubchem Compound ID91
Kegg IDC11457
ChemSpider ID89
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase
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

Protein Details
1. Putative 3-hydroxyphenylpropionic acid transporter
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
Protein Details
2. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
3. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
4. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
5. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368