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Record Information
Version	2.0
Creation Date	2012-05-31 14:03:57 -0600
Update Date	2015-06-03 15:54:41 -0600
Secondary Accession Numbers	ECMDB04061
Identification
Name:	3-(2,3-Dihydroxyphenyl)propionic acid
Description	3-(2,3-dihydroxyphenyl)propionate is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 3-(2,3-dihydroxyphenyl)propionate is invovled in Phenylalanine metabolism, Microbial metabolism in diverse environments, and Phenylpropionic acid degradation. The compound 3-(2,3-dihydroxyphenyl)propionate (DHPP) is a common intermediate of both pathways which must be cleaved by the MhpB dioxygenase before entering into the primary cell metabolism. (PMID 19520845)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x8bd6be5c> Close
Synonyms:	2,3-DHP 2,3-Dihydroxyphenylpropanoate 2,3-Dihydroxyphenylpropanoic acid 3-(2,3-Dihydroxyphenyl)propanoate 3-(2,3-Dihydroxyphenyl)propanoic acid 3-(2,3-Dihydroxyphenyl)propionate 3-(2,3-Dihydroxyphenyl)propionic acid 3-(2,3-Hihydroxyphenyl)propanoate 3-(2,3-Hihydroxyphenyl)propanoic acid 3-Carboxyethylcatechol
Chemical Formula:	C9H9O4
Weight:	Average: 181.1654 Monoisotopic: 181.050083776
InChI Key:	QZDSXQJWBGMRLU-UHFFFAOYSA-M
InChI:	InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,10,13H,4-5H2,(H,11,12)/p-1
CAS number:	Not Available
IUPAC Name:	3-(2-carboxyethyl)-2-hydroxybenzen-1-olate
Traditional IUPAC Name:	3-(2-carboxyethyl)-2-hydroxybenzenolate
SMILES:	OC(=O)CCC1=C(O)C([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.
Kingdom	Organic compounds
Super Class	Phenylpropanoids and polyketides
Class	Phenylpropanoic acids
Sub Class	Not Available
Direct Parent	Phenylpropanoic acids
Alternative Parents	Catechols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
Substituents	3-phenylpropanoic-acid Catechol 1-hydroxy-4-unsubstituted benzenoid 1-hydroxy-2-unsubstituted benzenoid Phenol Monocyclic benzene moiety Benzenoid Carboxylic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Carbonyl group Organic oxide Organic oxygen compound Organooxygen compound Hydrocarbon derivative Organic anion Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	monocarboxylic acid anion (CHEBI:46951 ) a small molecule (2-3-DIHYDROXYPHENYL-PROPIONATE )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 15.5 g/L ALOGPS logP 0.87 ALOGPS logP 1.45 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 3.84 ChemAxon pKa (Strongest Basic) -6.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 80.59 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 56.48 m³·mol⁻¹ ChemAxon Polarizability 17.31 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	3-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononadienedicarboxylate Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propionic acid + Hydrogen ion + NADH 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen <> 2-Hydroxy-6-ketononadienedicarboxylate cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion 3-(3-Hydroxyphenyl)propanoic acid + Oxygen + NADH + Hydrogen ion <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD Hydrogen ion + 3-(3-Hydroxyphenyl)propionate + NADH + Oxygen > Water + 3-(2,3-Dihydroxyphenyl)propionic acid + NAD cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > Hydrogen ion + 3-(2,3-Dihydroxyphenyl)propionic acid + NADH 3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-Dihydroxycinnamate 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioate cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion + Trans-2,3-Dihydroxycinnamate 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > (2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + Hydrogen ion
SMPDB Pathways:	2-Oxopent-4-enoate metabolism PW001890 2-Oxopent-4-enoate metabolism 2 PW002035 Phenylalanine metabolism PW000921
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 Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-0900000000-fdcde5f3ba7d533d8f82 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00e9-1900000000-11abd295c1bbf73df5cf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0c03-9700000000-7919444410991399e9c5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-0900000000-28645b93daffee16f771 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-2900000000-2bce8c4577dcaa36c5ec View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9100000000-4e4c53b32b94003f279c View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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 Manso, I., Torres, B., Andreu, J. M., Menendez, M., Rivas, G., Alfonso, C., Diaz, E., Garcia, J. L., Galan, B. (2009). "3-Hydroxyphenylpropionate and phenylpropionate are synergistic activators of the MhpR transcriptional regulator from Escherichia coli." J Biol Chem 284:21218-21228. Pubmed: 19520845 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 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)	Not Available
Links
External Links:	Resource Link CHEBI ID 46951 HMDB ID Not Available Pubchem Compound ID 9543123 Kegg ID C04044 ChemSpider ID 7822096 Wikipedia ID Not Available BioCyc ID 2-3-DIHYDROXYPHENYL-PROPIONATE EcoCyc ID 2-3-DIHYDROXYPHENYL-PROPIONATE

Enzymes