2-Hydroxy-6-ketononadienedicarboxylate (ECMDB04081) (M2MDB000599)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (30)
Record Information
Version2.0
Creation Date2012-05-31 14:04:23 -0600
Update Date2015-10-23 17:32:56 -0600
Secondary Accession Numbers
  • ECMDB04081
Identification
Name:2-Hydroxy-6-ketononadienedicarboxylate
Description2-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
Thumb
MOLSDFPDBSMILESInChI
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:152-154 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.27 g/LALOGPS
logP0.4ALOGPS
logP0.12ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area117.56 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.01 m³·mol⁻¹ChemAxon
Polarizability19.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 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
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
  • 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 ID19615
HMDB IDNot Available
Pubchem Compound ID21158453
Kegg IDC04479
ChemSpider ID20117996
Wikipedia IDNot Available
BioCyc IDCPD-157
EcoCyc IDCPD-157

Enzymes

Protein Details
1. 2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenase
General function:
Involved in iron ion binding
Specific function:
Catalyzes the non-heme iron(II)-dependent oxidative cleavage of 2,3-dihydroxyphenylpropionic acid and 2,3- dihydroxicinnamic acid into 2-hydroxy-6-ketononadienedioate and 2- hydroxy-6-ketononatrienedioate, respectively
Gene Name:
mhpB
Uniprot ID:
P0ABR9
Molecular weight:
34196
Reactions
3-(2,3-dihydroxyphenyl)propanoate + O(2) = 2-hydroxy-6-oxonona-2,4-diene-1,9-dioate.
(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + O(2) = 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate.
Protein Details
2. 2-hydroxy-6-oxononadienedioate/2-hydroxy-6-oxononatrienedioate hydrolase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the cleavage of the C5-C6 bond of 2-hydroxy-6- oxononadienedioate and 2-hydroxy-6-oxononatrienedioate, a dienol ring fission product of the bacterial meta-cleavage pathway for degradation of phenylpropionic acid
Gene Name:
mhpC
Uniprot ID:
P77044
Molecular weight:
32585
Reactions
(2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + succinate.
(2E,4Z,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + fumarate.