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
Description:2-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
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
DescriptionThis compound belongs to the class of chemical entities known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassKeto 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:
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 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
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

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.
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.