Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:38 UTC
HMDB IDHMDB01484
Secondary Accession Numbers
  • HMDB11665
Metabolite Identification
Common NameAcetoacetyl-CoA
DescriptionAcetoacetyl-CoA is an intermediate in the metabolism of Butanoate. It is a substrate for Succinyl-CoA:3-ketoacid-coenzyme A transferase 1 (mitochondrial), Hydroxymethylglutaryl-CoA synthase (mitochondrial), Short chain 3-hydroxyacyl-CoA dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), Hydroxymethylglutaryl-CoA synthase (cytoplasmic), Peroxisomal bifunctional enzyme, Acetyl-CoA acetyltransferase (cytosolic), Acetyl-CoA acetyltransferase (mitochondrial), 3-hydroxyacyl-CoA dehydrogenase type II, Succinyl-CoA:3-ketoacid-coenzyme A transferase 2 (mitochondrial), 3-ketoacyl-CoA thiolase (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal) and Trifunctional enzyme alpha subunit (mitochondrial).
Structure
Thumb
Synonyms
  1. 3-Acetoacetyl-CoA
  2. 3-Acetoacetyl-Coenzyme A
  3. 3-Oxobutyryl-CoA
  4. 3-Oxobutyryl-Coenzyme A
  5. Acetoacetyl coa
  6. Acetoacetyl coenzyme A
  7. Acetoacetyl-CoA
  8. Acetoacetyl-Coenzyme A
  9. S-Acetoacetylcoenzyme A
Chemical FormulaC25H40N7O18P3S
Average Molecular Weight851.607
Monoisotopic Molecular Weight851.136337737
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-oxobutanoyl)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-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number1420-36-6
SMILES
CC(=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=C1N=CN=C2N
InChI Identifier
InChI=1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20?,24-/m1/s1
InChI KeyOJFDKHTZOUZBOS-XBTRWLRFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Ketone
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct ParentAcyl CoAs
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Butanoate metabolism
  • Component of Fatty acid metabolism
  • Component of Propanoate metabolism
  • Component of Pyruvate metabolism
  • Component of Tryptophan metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility3.83 g/LALOGPS
logP-0.37ALOGPS
logP-6.8ChemAxon
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 count22ChemAxon
refractivity182.1ChemAxon
polarizability75.05ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
Pathways
NameSMPDB LinkKEGG Link
Butyrate MetabolismSMP00073map00650
Fatty acid MetabolismSMP00051map00071
Ketone Body MetabolismSMP00071map00072
Lysine DegradationSMP00037map00310
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480Not Available
Propanoate MetabolismSMP00016map00640
Pyruvate MetabolismSMP00060map00620
Steroid BiosynthesisSMP00023map00100
Valine, Leucine and Isoleucine DegradationSMP00032map00280
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 IDFDB022648
KNApSAcK IDNot Available
Chemspider ID388353
KEGG Compound IDC00332
BioCyc IDACETOACETYL-COA
BiGG ID34646
Wikipedia LinkAcetoacetyl-CoA
NuGOwiki LinkHMDB01484
Metagene LinkHMDB01484
METLIN ID449
PubChem Compound439214
PDB IDNot Available
ChEBI ID15345
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. Pubmed: 11489939

Enzymes

Gene Name:
ACAT2
Uniprot ID:
Q9BWD1
Reactions
Acetyl-CoA unknown Coenzyme A + Acetoacetyl-CoAdetails
Gene Name:
ACAT1
Uniprot ID:
P24752
Reactions
Acetyl-CoA unknown Coenzyme A + Acetoacetyl-CoAdetails
Gene Name:
HMGCS2
Uniprot ID:
P54868
Reactions
Acetyl-CoA + Water + Acetoacetyl-CoA unknown 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A unknown Acetyl-CoA + Water + Acetoacetyl-CoAdetails
Gene Name:
ACAA1
Uniprot ID:
P09110
Gene Name:
HMGCS1
Uniprot ID:
Q01581
Reactions
Acetyl-CoA + Water + Acetoacetyl-CoA unknown 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A unknown Acetyl-CoA + Water + Acetoacetyl-CoAdetails
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Gene Name:
EHHADH
Uniprot ID:
Q08426
Reactions
3-Hydroxybutyryl-CoA + NAD unknown Acetoacetyl-CoA + NADH + Hydrogen Iondetails
Gene Name:
HADH
Uniprot ID:
Q16836
Reactions
3-Hydroxybutyryl-CoA + NAD unknown Acetoacetyl-CoA + NADH + Hydrogen Iondetails
Gene Name:
HSD17B4
Uniprot ID:
P51659
Gene Name:
OXCT1
Uniprot ID:
P55809
Reactions
Succinyl-CoA + Acetoacetic acid unknown Succinic acid + Acetoacetyl-CoAdetails
Gene Name:
OXCT2
Uniprot ID:
Q9BYC2
Reactions
Succinyl-CoA + Acetoacetic acid unknown Succinic acid + Acetoacetyl-CoAdetails
Gene Name:
AACS
Uniprot ID:
Q86V21
Reactions
Adenosine triphosphate + Acetoacetic acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Acetoacetyl-CoAdetails
Gene Name:
HSD17B12
Uniprot ID:
Q53GQ0
Gene Name:
CRYL1
Uniprot ID:
Q9Y2S2