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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-01 17:12:18 UTC
HMDB IDHMDB0001484
Secondary Accession Numbers
  • HMDB0011665
  • HMDB01484
  • HMDB11665
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). In humans, acetoacetyl-CoA is involved in the metabolic disorder called the short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (HADH) pathway. Acetoacetyl-CoA is an intermediate in the metabolism of butanoate. It is a substrate for succinyl-CoA:3-ketoacid-coenzyme A transferase, hydroxymethylglutaryl-CoA synthase, short-chain 3-hydroxyacyl-CoA dehydrogenase, peroxisomal bifunctional enzyme, acetyl-CoA acetyltransferase, and 3-ketoacyl-CoA thiolase.
Structure
Data?1588353137
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 Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-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 Nameacetoacetyl-coa
CAS Registry Number1420-36-6
SMILES
CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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-5.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity182.1 m³·mol⁻¹ChemAxon
Polarizability76.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0004009000-9559fa356f1bae03b7caSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0269300000-d5574d3fd84812c0057dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-05n1-0009600000-a29b94fc4d454c655babSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0001209000-21979fdba010c3871c5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0udi-0000000090-aa1f97ad009df4ad9439Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 57V, negativesplash10-0udi-0000100490-97b56edeb43a5d82ba85Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, negativesplash10-014i-0000910830-9d7a9bb5d2817f98fbf1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 93V, negativesplash10-0ar9-0101901000-ee3c1d5ebb3142f3c5afSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 115V, negativesplash10-0a6r-5524900000-2d745cfa452462059e2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 136V, negativesplash10-056r-9513200000-037d88669e973d0dff1cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-004i-9400000000-fca9f3020e4e007e8164Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 187V, negativesplash10-004i-9300000000-13ad94b2682d99b6234dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 216V, negativesplash10-004i-9200000000-32dfa0b8d343e2eb7b7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 260V, negativesplash10-004i-9100000000-6461ef6280ce0db781b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-014i-0000000900-727bb0c3c925e7bbeba4Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00di-0190000000-0e093fb5398057b2093dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0900000000-b4c90f8c858e783159b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0udl-0018900000-91aaf6888a10aac16f57Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00xr-0092000000-2dd3c44dfb7a39ee9a59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-163ca7231778bddd9739Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-4f4f26abcf9b0d9f285eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-cc9acdeb298fa6ebbdb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9730140350-cefdc8a0886f8e9e2b86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910110010-51e3282fd98f872b9ff5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-4a6e405bfbd488ea01d4Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAT2
Uniprot ID:
Q9BWD1
Molecular weight:
41350.5
Reactions
Acetyl-CoA → Coenzyme A + Acetoacetyl-CoAdetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Plays a major role in ketone body metabolism.
Gene Name:
ACAT1
Uniprot ID:
P24752
Molecular weight:
45199.2
Reactions
Acetyl-CoA → Coenzyme A + Acetoacetyl-CoAdetails
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
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:
P54868
Molecular weight:
52481.065
Reactions
Acetyl-CoA + Water + Acetoacetyl-CoA → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A → Acetyl-CoA + Water + Acetoacetyl-CoAdetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS1
Uniprot ID:
Q01581
Molecular weight:
57293.105
Reactions
Acetyl-CoA + Water + Acetoacetyl-CoA → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A → Acetyl-CoA + Water + Acetoacetyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Molecular weight:
25983.695
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
3-Hydroxybutyryl-CoA + NAD → Acetoacetyl-CoA + NADH + Hydrogen Iondetails
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:
HADH
Uniprot ID:
Q16836
Molecular weight:
36035.11
Reactions
3-Hydroxybutyryl-CoA + NAD → Acetoacetyl-CoA + NADH + Hydrogen Iondetails

Only showing the first 10 proteins. There are 19 proteins in total.