Record Information
Version2.0
Creation Date2012-05-31 14:26:51 -0600
Update Date2015-06-03 17:19:17 -0600
Secondary Accession Numbers
  • ECMDB20089
Identification
Name:4-Hydroxy-2-oxohexanoic acid
Description4-hydroxy-2-oxohexanoic acid 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:
  • 2-Oxo-4-hydroxy-hexanoate
  • 2-Oxo-4-hydroxy-hexanoic acid
  • 4-Hydroxy-2-oxohexanoate
Chemical Formula:C6H10O4
Weight:Average: 146.1412
Monoisotopic: 146.057908808
InChI Key:ALFQPWXBAWHVDP-UHFFFAOYSA-N
InChI:InChI=1S/C6H10O4/c1-2-4(7)3-5(8)6(9)10/h4,7H,2-3H2,1H3,(H,9,10)
CAS number:Not Available
IUPAC Name:4-hydroxy-2-oxohexanoic acid
Traditional IUPAC Name:4-hydroxy-2-oxohexanoic acid
SMILES:CCC(O)CC(=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
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility45.7 g/LALOGPS
logP-0.42ALOGPS
logP0.42ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.33 m³·mol⁻¹ChemAxon
Polarizability13.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Collection of Reactions without pathwaysPW001891 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Toluene and xylene degradation ec00622
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-e701631dcfe73ca530a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08ir-9600000000-e121fb7047d2b9da4f10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-afb60287a16bc748cd52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3900000000-f4f9e29d250da9a21011View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fgt-9400000000-b42c624290da9744b821View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f7fad3d8922a4206f325View 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID441164
Kegg IDC06762
ChemSpider ID389953
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in 4-hydroxy-2-oxovalerate aldolase activity
Specific function:
Catalyzes the retro-aldol cleavage of 4-hydroxy-2- oxopentanoate to pyruvate and acetaldehyde. Is involved in the meta-cleavage pathway for the degradation of 3-phenylpropanoate
Gene Name:
mhpE
Uniprot ID:
P51020
Molecular weight:
36470
Reactions
4-hydroxy-2-oxopentanoate = acetaldehyde + pyruvate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of 2-hydroxypentadienoic acid (enolic form of 2-oxopent-4-enoate) to 4-hydroxy-2-ketopentanoic acid
Gene Name:
mhpD
Uniprot ID:
P77608
Molecular weight:
28890
Reactions
4-hydroxy-2-oxopentanoate = 2-oxopent-4-enoate + H(2)O.