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Record Information
Version	2.0
Creation Date	2012-05-31 14:26:01 -0600
Update Date	2015-06-03 17:19:15 -0600
Secondary Accession Numbers	ECMDB20072
Identification
Name:	3-Hydroxy-5-oxohexanoate
Description	3-hydroxy-5-oxohexanoate 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. It is a substrate for butyryl coenzyme A transferase (EC 2.8.3.8) and it sometimes an associated byproduct of gallic acid degradation.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xacea12ec> Close
Synonyms:	3-Hydroxy-5-ketohexanoate 3-Hydroxy-5-ketohexanoic acid 3-Hydroxy-5-oxo-Hexanoate 3-Hydroxy-5-oxo-Hexanoic acid 3-Hydroxy-5-oxohexanoic acid
Chemical Formula:	C6H10O4
Weight:	Average: 146.1412 Monoisotopic: 146.057908808
InChI Key:	APWDZEIBFNZVND-UHFFFAOYSA-N
InChI:	InChI=1S/C6H10O4/c1-4(7)2-5(8)3-6(9)10/h5,8H,2-3H2,1H3,(H,9,10)
CAS number:	109138-72-9
IUPAC Name:	3-hydroxy-5-oxohexanoic acid
Traditional IUPAC Name:	3-hydroxy-5-oxohexanoic acid
SMILES:	CC(=O)CC(O)CC(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Hydroxy acids and derivatives
Sub Class	Medium-chain hydroxy acids and derivatives
Direct Parent	Medium-chain hydroxy acids and derivatives
Alternative Parents	Medium-chain fatty acids Hydroxy fatty acids Beta hydroxy acids and derivatives Beta-hydroxy ketones Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Medium-chain hydroxy acid Medium-chain fatty acid Beta-hydroxy acid Hydroxy fatty acid Fatty acyl Fatty acid Beta-hydroxy ketone Secondary alcohol Ketone Carboxylic acid Carboxylic acid derivative Monocarboxylic acid or derivatives Organic oxygen compound Organic oxide Carbonyl group Alcohol Hydrocarbon derivative Organooxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	3-hydroxy monocarboxylic acid (CHEBI:37032 ) 5-oxo monocarboxylic acid (CHEBI:37032 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 124 g/L ALOGPS logP -0.88 ALOGPS logP -0.7 ChemAxon logS -0.07 ALOGPS pKa (Strongest Acidic) 4.18 ChemAxon pKa (Strongest Basic) -2.9 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 33.05 m³·mol⁻¹ ChemAxon Polarizability 13.85 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-Hydroxy-5-oxohexanoate + Acetyl-CoA <> 3-Hydroxy-5-oxohexanoyl-CoA + Acetic acid Acetyl-CoA + 3-Hydroxy-5-oxohexanoate > Acetic acid + 3-Hydroxy-5-oxohexanoyl-CoA + 3-Hydroxy-5-oxohexanoyl-CoA
SMPDB Pathways:	Aminobenzoate Degradation PW000757
KEGG Pathways:	1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01t9-1900000000-90969318dfa8afeae175 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03fr-6900000000-24ab4e6ca727e075be58 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-02tc-9100000000-98661dd6646934521b4a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f92-2900000000-e4a3a0b79be7d7b45d0d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-9600000000-5695ceb1b8b5bdd87a0e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-5a4a40264de0ba231481 View in MoNA 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 37032 HMDB ID Not Available Pubchem Compound ID 376 Kegg ID C16272 ChemSpider ID 367 Wikipedia ID Not Available BioCyc ID CPD-19 EcoCyc ID CPD-19

Enzymes