Record Information
Version3.6
Creation Date2006-08-13 07:50:32 UTC
Update Date2013-02-09 00:12:51 UTC
HMDB IDHMDB03943
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Oxohexanoyl-CoA
Description3-Oxohexanoyl-CoA is an intermediate in Fatty acid elongation in mitochondria. 3-Oxohexanoyl-CoA is the 3rd to last step in the synthesis of Hexanoyl-CoA and is converted from Butanoyl-CoA via the enzyme acetyl-CoA acyltransferase 2 (EC 2.3.1.16). It is then converted to (S)-Hydroxyhexanoyl-CoA via the 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35).
Structure
Thumb
Synonyms
  1. 3-Ketohexanoyl CoA.
  2. 3-Ketohexanoyl Coenzyme A.
  3. 3-Oxohexanoyl-CoA
  4. 3-Oxohexanoyl-Coenzyme A
  5. Ketohexanoyl-CoA
  6. Ketohexanoyl-Coenzyme A
Chemical FormulaC27H44N7O18P3S
Average Molecular Weight879.661
Monoisotopic Molecular Weight879.167637865
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxohexanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxohexanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number19774-86-8
SMILES
CCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C27H44N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-14,16,20-22,26,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t16-,20-,21-,22?,26-/m1/s1
InChI KeyNFOYYXQAVVYWKV-ZOGSZLKASA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl CoAs
Other Descriptors
  • Acyl CoAs
  • Aromatic Heteropolycyclic Compounds
  • Fatty acyl CoAs(KEGG)
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Ketone
  • Mixed Pentose/Hexose Disaccharide
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent3-Oxo-acyl CoAs
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.064Not Available
Predicted Properties
PropertyValueSource
water solubility3.43 g/LALOGPS
logP-0.04ALOGPS
logP-5.6ChemAxon
logS-2.4ALOGPS
pKa (strongest acidic)0.83ChemAxon
pKa (strongest basic)4.95ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count18ChemAxon
hydrogen donor count9ChemAxon
polar surface area380.7ChemAxon
rotatable bond count24ChemAxon
refractivity191.33ChemAxon
polarizability77.82ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid Elongation In MitochondriaSMP00054map00062
Fatty acid MetabolismSMP00051map00071
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023262
KNApSAcK IDNot Available
Chemspider ID389508
KEGG Compound IDC05269
BioCyc IDK-HEXANOYL-COA
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03943
Metagene LinkHMDB03943
METLIN IDNot Available
PubChem Compound440610
PDB IDNot Available
ChEBI ID27648
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
ACAT2
Uniprot ID:
Q9BWD1
Reactions
Acetyl-CoA + Butyryl-CoA unknown Coenzyme A + 3-Oxohexanoyl-CoAdetails
Gene Name:
ACAA2
Uniprot ID:
P42765
Reactions
Acetyl-CoA + Butyryl-CoA unknown Coenzyme A + 3-Oxohexanoyl-CoAdetails
Gene Name:
ACAT1
Uniprot ID:
P24752
Reactions
Acetyl-CoA + Butyryl-CoA unknown Coenzyme A + 3-Oxohexanoyl-CoAdetails
Gene Name:
ACAA1
Uniprot ID:
P09110
Reactions
Acetyl-CoA + Butyryl-CoA unknown Coenzyme A + 3-Oxohexanoyl-CoAdetails
Gene Name:
HADHB
Uniprot ID:
P55084
Reactions
Acetyl-CoA + Butyryl-CoA unknown Coenzyme A + 3-Oxohexanoyl-CoAdetails
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Gene Name:
EHHADH
Uniprot ID:
Q08426
Reactions
(S)-Hydroxyhexanoyl-CoA + NAD unknown 3-Oxohexanoyl-CoA + NADH + Hydrogen Iondetails
Gene Name:
HADH
Uniprot ID:
Q16836
Reactions
(S)-Hydroxyhexanoyl-CoA + NAD unknown 3-Oxohexanoyl-CoA + NADH + Hydrogen Iondetails
Gene Name:
HADHA
Uniprot ID:
P40939
Reactions
(S)-Hydroxyhexanoyl-CoA + NAD unknown 3-Oxohexanoyl-CoA + NADH + Hydrogen Iondetails
Gene Name:
HSD17B4
Uniprot ID:
P51659