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Record Information
Version1.0
Creation Date2016-09-30 22:46:35 UTC
Update Date2020-05-21 16:28:42 UTC
BMDB IDBMDB0001484
Secondary Accession Numbers
  • BMDB01484
Metabolite Identification
Common NameAcetoacetyl-CoA
DescriptionAcetoacetyl-CoA belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group. Acetoacetyl-CoA is a strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
3-Acetoacetyl-CoAChEBI
Acetoacetyl coenzyme AChEBI
S-Acetoacetyl-CoAChEBI
S-Acetoacetyl-coenzym aChEBI
S-Acetoacetyl-coenzyme AChEBI
Acetoacetyl CoAMeSH
Chemical FormulaC25H40N7O18P3S
Average Molecular Weight851.607
Monoisotopic Molecular Weight851.136337737
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number1420-36-6
SMILESNot Available
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-CITAKDKDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassAminopiperidines
Direct ParentAminopiperidines
Alternative Parents
Substituents
  • 4-aminopiperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001484
DrugBank IDDB03059
Phenol Explorer Compound IDNot Available
FooDB IDFDB022648
KNApSAcK IDC00007269
Chemspider ID83198
KEGG Compound IDC00332
BioCyc IDACETOACETYL-COA
BiGG IDNot Available
Wikipedia LinkAcetoacetyl-CoA
METLIN IDNot Available
PubChem Compound92153
PDB IDNot Available
ChEBI ID15345
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS2
Uniprot ID:
Q2KIE6
Molecular weight:
56895.0
Reactions
Acetyl-CoA + Acetoacetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
General function:
Lipid transport and metabolism
Specific function:
In the production of energy from fats, this is one of the enzymes that catalyzes the last step of the mitochondrial beta-oxidation pathway, an aerobic process breaking down fatty acids into acetyl-CoA. Using free coenzyme A/CoA, catalyzes the thiolytic cleavage of medium- to long-chain unbranched 3-oxoacyl-CoAs into acetyl-CoA and a fatty acyl-CoA shortened by two carbon atoms. Also catalyzes the condensation of two acetyl-CoA molecules into acetoacetyl-CoA and could be involved in the production of ketone bodies. Also displays hydrolase activity on various fatty acyl-CoAs (By similarity). Thereby, could be responsible for the production of acetate in a side reaction to beta-oxidation (By similarity). Abolishes BNIP3-mediated apoptosis and mitochondrial damage (By similarity).
Gene Name:
ACAA2
Uniprot ID:
Q3T0R7
Molecular weight:
42131.0
Reactions
Coenzyme A + Acetoacetyl-CoA →2 Acetyl-CoAdetails
General function:
Lipid transport and metabolism
Specific function:
This is one of the enzymes that catalyzes the last step of the mitochondrial beta-oxidation pathway, an aerobic process breaking down fatty acids into acetyl-CoA. Using free coenzyme A/CoA, catalyzes the thiolytic cleavage of medium- to long-chain 3-oxoacyl-CoAs into acetyl-CoA and a fatty acyl-CoA shortened by two carbon atoms. The activity of the enzyme is reversible and it can also catalyze the condensation of two acetyl-CoA molecules into acetoacetyl-CoA. Thereby, it plays a major role in ketone body metabolism.
Gene Name:
ACAT1
Uniprot ID:
Q29RZ0
Molecular weight:
44889.0
Reactions
2 Acetyl-CoA → Acetoacetyl-CoA + Coenzyme Adetails
Coenzyme A + Acetoacetyl-CoA →2 Acetyl-CoAdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
ACSS2
Uniprot ID:
A7YWF1
Molecular weight:
78734.0
Reactions
Acetoacetyl-CoA + Adenosine monophosphate + Pyrophosphate → Acetyl adenylate + Acetaldehyde + Adenosine triphosphatedetails
General function:
Not Available
Specific function:
Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate.
Gene Name:
OXCT1
Uniprot ID:
Q24JZ7
Molecular weight:
56453.0
Reactions
Acetoacetic acid + Succinyl-CoA → Succinic acid + Acetoacetyl-CoAdetails
Acetoacetic acid + Succinyl-CoA → Acetoacetyl-CoA + Succinic aciddetails