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Record Information
Version	2.0
Creation Date	2012-05-31 14:04:23 -0600
Update Date	2015-10-23 17:32:56 -0600
Secondary Accession Numbers	ECMDB04081
Identification
Name:	2-Hydroxy-6-ketononadienedicarboxylate
Description	2-hydroxy-6-ketononadienedicarboxylate is an intermediate in phenylalanine metabolism. It is converted from 2,3-dihydroxy-phenylpropanoate by 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (EC:1.13.11.-), and form succinate and cis-2-hydroxypenta-2,4-dienoate by 2-hydroxy-6-ketonona-2,4-dienedioic acid hydrolase (EC:3.7.1.-) (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa9e79f60> Close
Synonyms:	(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioic acid 2-Hydroxy-6-keto-nona-2,4-dienedioate 2-Hydroxy-6-keto-nona-2,4-dienedioic acid 2-Hydroxy-6-ketonona-2,4-dienedioate 2-Hydroxy-6-ketonona-2,4-dienedioic acid 2-Hydroxy-6-ketononadienedicarboxylate 2-Hydroxy-6-ketononadienedicarboxylic acid 2-Hydroxy-6-ketononadienedioate 2-Hydroxy-6-ketononadienedioic acid 2-Hydroxy-6-oxo-nona-2,4-diene 1,9-dicarboxylate 2-Hydroxy-6-oxo-nona-2,4-diene 1,9-dicarboxylic acid 2-Hydroxy-6-oxonona-2,4-diene-1,9-dioate 2-Hydroxy-6-oxonona-2,4-diene-1,9-dioic acid 2-Hydroxy-6-oxonona-2,4-dienedioate 2-Hydroxy-6-oxonona-2,4-dienedioic acid
Chemical Formula:	C9H8O6
Weight:	Average: 212.158 Monoisotopic: 212.033185137
InChI Key:	RFENOVFRMPRRJI-YDCWOTKKSA-L
InChI:	InChI=1S/C9H10O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-3,11H,4-5H2,(H,12,13)(H,14,15)/p-2/b2-1+,7-3-
CAS number:	53-42-9
IUPAC Name:	(2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate
Traditional IUPAC Name:	(2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate
SMILES:	O\C(=C/C=C/C(=O)CCC([O-])=O)C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Medium-chain keto acids and derivatives
Direct Parent	Medium-chain keto acids and derivatives
Alternative Parents	Gamma-keto acids and derivatives Unsaturated fatty acids Dicarboxylic acids and derivatives Enones Acryloyl compounds Ketones Enolates Carboxylic acids Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Medium-chain keto acid Gamma-keto acid Dicarboxylic acid or derivatives Fatty acyl Unsaturated fatty acid Acryloyl-group Enone Alpha,beta-unsaturated ketone Ketone Carboxylic acid derivative Carboxylic acid Enolate Carbonyl group Organic oxide Organic oxygen compound Hydrocarbon derivative Organooxygen compound Organic anion Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	2-hydroxy-6-oxonona-2,4-dienedioate (CHEBI:66887 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	152-154 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 7.27 g/L ALOGPS logP 0.4 ALOGPS logP 0.12 ChemAxon logS -1.5 ALOGPS pKa (Strongest Acidic) 3.25 ChemAxon pKa (Strongest Basic) -5.4 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 117.56 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 73.01 m³·mol⁻¹ ChemAxon Polarizability 19.1 ų ChemAxon Number of Rings 0 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-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononadienedicarboxylate Water + 2-Hydroxy-6-ketononadienedicarboxylate > Hydrogen ion + 2-Hydroxy-2,4-pentadienoate + Succinic acid 2-Hydroxy-2,4-pentadienoate + Succinic acid <> 2-Hydroxy-6-ketononadienedicarboxylate + Water 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen <> 2-Hydroxy-6-ketononadienedicarboxylate 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioate 2-Hydroxy-6-ketononadienedicarboxylate + Water + 2-Hydroxy-6-ketononatrienedioate <> Succinic acid + Fumaric acid
SMPDB Pathways:	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 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 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
Links
External Links:	Resource Link CHEBI ID 19615 HMDB ID Not Available Pubchem Compound ID 21158453 Kegg ID C04479 ChemSpider ID 20117996 Wikipedia ID Not Available BioCyc ID CPD-157 EcoCyc ID CPD-157

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