Showing metabocard for Acetoacetyl-CoA (BMDB0001484)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
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
MOLSDFPDBSMILESInChI
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
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 Properties
PropertyValueSource
logP-0.24ALOGPS
logP-5.7ChemAxon
logS-2.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0004009000-9559fa356f1bae03b7caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0269300000-d5574d3fd84812c0057dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-05n1-0009600000-a29b94fc4d454c655babView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0001209000-21979fdba010c3871c5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0udi-0000000090-aa1f97ad009df4ad9439View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 57V, negativesplash10-0udi-0000100490-97b56edeb43a5d82ba85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, negativesplash10-014i-0000910830-9d7a9bb5d2817f98fbf1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 93V, negativesplash10-0ar9-0101901000-ee3c1d5ebb3142f3c5afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 115V, negativesplash10-0a6r-5524900000-2d745cfa452462059e2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 136V, negativesplash10-056r-9513200000-037d88669e973d0dff1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-004i-9400000000-fca9f3020e4e007e8164View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 187V, negativesplash10-004i-9300000000-13ad94b2682d99b6234dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 216V, negativesplash10-004i-9200000000-32dfa0b8d343e2eb7b7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 260V, negativesplash10-004i-9100000000-6461ef6280ce0db781b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-014i-0000000900-727bb0c3c925e7bbeba4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00di-0190000000-0e093fb5398057b2093dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0900000000-b4c90f8c858e783159b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0udl-0018900000-91aaf6888a10aac16f57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00xr-0092000000-2dd3c44dfb7a39ee9a59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0670-0000904200-f3bcbcab3db17ae6a02aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00di-0190000000-3a982abdcfdcfe6b0420View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0udr-0027900000-0d41e18ae4bea1b5b7ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, positivesplash10-0002-6900000000-959cba779002108c94ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, positivesplash10-00di-9000000000-9fd58d8b09e3b71e5e6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, positivesplash10-03di-0190000000-aa6e0456b3c35ec78a6aView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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

Enzyme Details
1. Hydroxymethylglutaryl-CoA synthase, mitochondrial
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
Enzyme Details
2. 3-ketoacyl-CoA thiolase, mitochondrial
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
Enzyme Details
3. Acetyl-CoA acetyltransferase, mitochondrial
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
Enzyme Details
4. ACSS2 protein
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
Enzyme Details
5. Succinyl-CoA:3-ketoacid-coenzyme A transferase
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