Record Information
Version2.0
Creation Date2012-05-31 13:53:16 -0600
Update Date2015-09-17 15:41:12 -0600
Secondary Accession Numbers
  • ECMDB01484
Identification
Name:Acetoacetyl-CoA
DescriptionAcetoacetyl-CoA is an intermediate in the metabolism of Butanoate. It is a substrate for Succinyl-CoA:3-ketoacid-coenzyme A transferase 1, Hydroxymethylglutaryl-CoA synthase , Short chain 3-hydroxyacyl-CoA dehydrogenase, Acetyl-CoA acetyltransferase, 3-hydroxyacyl-CoA dehydrogenase type , Succinyl-CoA:3-ketoacid-coenzyme A transferase 2, and 3-ketoacyl-CoA thiolase.
Structure
Thumb
Synonyms:
  • 3-Acetoacetyl-CoA
  • 3-Acetoacetyl-Coenzyme A
  • 3-Oxobutyryl-CoA
  • 3-Oxobutyryl-Coenzyme A
  • Acetoacetyl coa
  • Acetoacetyl coenzyme A
  • Acetoacetyl-S-CoA
  • Acetoacetyl-CoA
  • Acetoacetyl-Coenzyme A
  • Acetoacetyl-S-CoA
  • S-Acetoacetylcoenzyme A
Chemical Formula:C25H40N7O18P3S
Weight:Average: 851.607
Monoisotopic: 851.136337737
InChI Key:OJFDKHTZOUZBOS-XBTRWLRFSA-N
InChI: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
CAS number:1420-36-6
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 IUPAC Name:acetoacetyl-coa
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
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
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.84 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Acetate metabolismPW002090 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid metabolismPW000796 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
fatty acid oxidation (Butanoate)PW001017 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
22± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
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 SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15345
HMDB IDHMDB01484
Pubchem Compound ID439214
Kegg IDC00332
ChemSpider ID388353
WikipediaAcetoacetyl-CoA
BioCyc IDACETOACETYL-COA
EcoCyc IDACETOACETYL-COA
Ligand ExpoCAA

Enzymes

General function:
Involved in acetyl-CoA C-acyltransferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadA
Uniprot ID:
P21151
Molecular weight:
40876
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Could possibly oxidize fatty acids using specific components
Gene Name:
paaF
Uniprot ID:
P76082
Molecular weight:
27237
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3- acetoacetyl-CoA + NADPH
Gene Name:
paaH
Uniprot ID:
P76083
Molecular weight:
51732
Reactions
(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3-acetoacetyl-CoA + NADPH.
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoD
Uniprot ID:
P76458
Molecular weight:
23526
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoA
Uniprot ID:
P76459
Molecular weight:
22960
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
2 acetyl-CoA = CoA + acetoacetyl-CoA
Gene Name:
atoB
Uniprot ID:
P76461
Molecular weight:
40352
Reactions
2 acetyl-CoA = CoA + acetoacetyl-CoA.
General function:
Involved in transferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:
fadI
Uniprot ID:
P76503
Molecular weight:
46530
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:
fadJ
Uniprot ID:
P77399
Molecular weight:
77072
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
2 acetyl-CoA = CoA + acetoacetyl-CoA
Gene Name:
yqeF
Uniprot ID:
Q46939
Molecular weight:
41018
Reactions
2 acetyl-CoA = CoA + acetoacetyl-CoA.

Transporters

General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.