2-Hydroxy-6-ketononatrienedioate (ECMDB20042) (M2MDB000891)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (30)
Record Information
Version2.0
Creation Date2012-05-31 14:24:24 -0600
Update Date2015-06-03 17:19:11 -0600
Secondary Accession Numbers
  • ECMDB20042
Identification
Name:2-Hydroxy-6-ketononatrienedioate
Description2-hydroxy-6-ketononatrienedioate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2E,4Z,7E)-2-hydroxy-6-oxononatrienedioate
  • (2E,4Z,7E)-2-hydroxy-6-oxononatrienedioate
  • (2E,4Z,7E)-2-hydroxy-6-oxononatrienedioic acid
  • 2-hydroxy-6-ketononatrienedioate
  • 2-Hydroxy-6-ketononatrienedioic acid
  • 2-Hydroxy-6-oxonona-2,4,7-triene-1,9-dioate
  • 2-Hydroxy-6-oxonona-2,4,7-triene-1,9-dioic acid
  • 2-Hydroxy-6-oxonona-2,4,7-trienedioate
  • 2-Hydroxy-6-oxonona-2,4,7-trienedioic acid
  • 2-Hydroxy-6-oxononatrienedioate
  • 2-Hydroxy-6-oxononatrienedioic acid
Chemical Formula:C9H8O6
Weight:Average: 212.1562
Monoisotopic: 212.032087988
InChI Key:WCJYZUFKKTYNLB-UHFFFAOYSA-N
InChI:InChI=1S/C9H8O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-5,11H,(H,12,13)(H,14,15)
CAS number:Not Available
IUPAC Name:2-hydroxy-6-oxonona-2,4,7-trienedioic acid
Traditional IUPAC Name:2-hydroxy-6-oxonona-2,4,7-trienedioic acid
SMILES:OC(=O)C=CC(=O)C=CC=C(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
  • Hydroxy fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Unsaturated fatty acid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP0.57ALOGPS
logP0.48ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)2.71ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity52.41 m³·mol⁻¹ChemAxon
Polarizability19.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Trans-2,3-Dihydroxycinnamate + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate
Water + 2-Hydroxy-6-ketononatrienedioate > Fumaric acid + Hydrogen ion + 2-Hydroxy-2,4-pentadienoate
Trans-2,3-Dihydroxycinnamate + Oxygen <> 2-Hydroxy-6-ketononatrienedioate
2-Hydroxy-6-ketononatrienedioate + Water <> 2-Hydroxy-2,4-pentadienoate + Fumaric acid
Trans-2,3-Dihydroxycinnamate + Oxygen > 2-Hydroxy-6-ketononatrienedioate
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
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + Oxygen + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate
2-Hydroxy-6-ketononatrienedioate + Water > Hydrogen ion + Fumaric acid + 2-Hydroxy-2,4-pentadienoate + 2-Hydroxy-2,4-pentadienoate
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:
  • cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0910000000-f85b10b07bb579efc893View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-3900000000-0879959330a9e6ffdb4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-9500000000-b8b332e9dd93e7c93793View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3960000000-2949128314cb5443a31fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bd-3910000000-05954caccf389b0f8c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-8900000000-137ae589ef490c37a808View 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID31082
HMDB IDNot Available
Pubchem Compound ID5282147
Kegg IDC12624
ChemSpider ID4445344
Wikipedia IDNot Available
BioCyc IDCPD0-2184
EcoCyc IDCPD0-2184

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.