Human Metabolome Database Version 3.5

Showing metabocard for Acetoacetyl-CoA (HMDB01484)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:38 -0700
HMDB ID HMDB01484
Secondary Accession Numbers
  • HMDB11665
Metabolite Identification
Common Name Acetoacetyl-CoA
Description Acetoacetyl-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C25H40N7O18P3S
Average Molecular Weight 851.607
Monoisotopic Molecular Weight 851.136337737
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 Number 1420-36-6
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 Key OJFDKHTZOUZBOS-XBTRWLRFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl 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 Parent Acyl CoAs
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.83 g/L ALOGPS
LogP -0.37 ALOGPS
LogP -6.8 ChemAxon
LogS -2.35 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 380.7 A2 ChemAxon
Rotatable Bond Count 22 ChemAxon
Refractivity 182.1 ChemAxon
Polarizability 75.05 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biofluid Locations Not Available
Tissue Location
  • Fibroblasts
Pathways
Name SMPDB Link KEGG Link
Butyrate Metabolism SMP00073 map00650 Link_out
Fatty acid Metabolism SMP00051 map00071 Link_out
Valine, Leucine and Isoleucine Degradation SMP00032 map00280 Link_out
Propanoate Metabolism SMP00016 map00640 Link_out
Steroid Biosynthesis SMP00023 map00100 Link_out
Lysine Degradation SMP00037 map00310 Link_out
Ketone Body Metabolism SMP00071 map00072 Link_out
Pyruvate Metabolism SMP00060 map00620 Link_out
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids SMP00480 Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022648
KNApSAcK ID Not Available
Chemspider ID 388353 Link_out
KEGG Compound ID C00332 Link_out
BioCyc ID ACETOACETYL-COA Link_out
BiGG ID 34646 Link_out
Wikipedia Link Acetoacetyl-CoA Link_out
NuGOwiki Link HMDB01484 Link_out
Metagene Link HMDB01484 Link_out
METLIN ID 449 Link_out
PubChem Compound 439214 Link_out
PDB ID Not Available
ChEBI ID 15345 Link_out
References
Synthesis Reference Not 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 Link_out

Enzymes
Name: Acetyl-CoA acetyltransferase, cytosolic
Reactions:
Acetyl-CoA unknown Coenzyme A + Acetoacetyl-CoA details
Gene Name: ACAT2
Uniprot ID: Q9BWD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketoacyl-CoA thiolase, mitochondrial
Reactions: Not Available
Gene Name: ACAA2
Uniprot ID: P42765 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acetyl-CoA acetyltransferase, mitochondrial
Reactions:
Acetyl-CoA unknown Coenzyme A + Acetoacetyl-CoA details
Gene Name: ACAT1
Uniprot ID: P24752 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hydroxymethylglutaryl-CoA synthase, mitochondrial
Reactions:
Acetyl-CoA + Water + Acetoacetyl-CoA unknown 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A details
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A unknown Acetyl-CoA + Water + Acetoacetyl-CoA details
Gene Name: HMGCS2
Uniprot ID: P54868 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketoacyl-CoA thiolase, peroxisomal
Reactions: Not Available
Gene Name: ACAA1
Uniprot ID: P09110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit beta, mitochondrial
Reactions: Not Available
Gene Name: HADHB
Uniprot ID: P55084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hydroxymethylglutaryl-CoA synthase, cytoplasmic
Reactions:
Acetyl-CoA + Water + Acetoacetyl-CoA unknown 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A details
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A unknown Acetyl-CoA + Water + Acetoacetyl-CoA details
Gene Name: HMGCS1
Uniprot ID: Q01581 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-hydroxyacyl-CoA dehydrogenase type-2
Reactions: Not Available
Gene Name: HSD17B10
Uniprot ID: Q99714 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal bifunctional enzyme
Reactions:
3-Hydroxybutyryl-CoA + NAD unknown Acetoacetyl-CoA + NADH + Hydrogen Ion details
Gene Name: EHHADH
Uniprot ID: Q08426 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial
Reactions:
3-Hydroxybutyryl-CoA + NAD unknown Acetoacetyl-CoA + NADH + Hydrogen Ion details
Gene Name: HADH
Uniprot ID: Q16836 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit alpha, mitochondrial
Reactions: Not Available
Gene Name: HADHA
Uniprot ID: P40939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal multifunctional enzyme type 2
Reactions: Not Available
Gene Name: HSD17B4
Uniprot ID: P51659 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial
Reactions:
Succinyl-CoA + Acetoacetic acid unknown Succinic acid + Acetoacetyl-CoA details
Gene Name: OXCT1
Uniprot ID: P55809 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrial
Reactions:
Succinyl-CoA + Acetoacetic acid unknown Succinic acid + Acetoacetyl-CoA details
Gene Name: OXCT2
Uniprot ID: Q9BYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acetoacetyl-CoA synthetase
Reactions:
Adenosine triphosphate + Acetoacetic acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Acetoacetyl-CoA details
Gene Name: AACS
Uniprot ID: Q86V21 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estradiol 17-beta-dehydrogenase 12
Reactions: Not Available
Gene Name: HSD17B12
Uniprot ID: Q53GQ0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lambda-crystallin homolog
Reactions: Not Available
Gene Name: CRYL1
Uniprot ID: Q9Y2S2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Elongation of very long chain fatty acids protein 2
Reactions: Not Available
Gene Name: ELOVL2
Uniprot ID: Q9NXB9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Elongation of very long chain fatty acids protein 1
Reactions: Not Available
Gene Name: ELOVL1
Uniprot ID: Q9BW60 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA