acetoacetyl-CoA (YMDB00529)

Identification
YMDB IDYMDB00529
Nameacetoacetyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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
  • 3-acetoacetyl-CoA
  • 3-acetoacetyl-Coenzyme A
  • 3-oxobutyryl-CoA
  • 3-oxobutyryl-Coenzyme A
  • Acetoacetyl coa
  • Acetoacetyl coenzyme A
  • acetoacetyl-CoA
  • acetoacetyl-Coenzyme A
  • S-Acetoacetylcoenzyme A
  • S-Acetoacetyl-CoA
  • S-Acetoacetyl-coenzym a
  • S-Acetoacetyl-coenzyme A
CAS number1420-36-6
WeightAverage: 851.607
Monoisotopic: 851.136337737
InChI KeyOJFDKHTZOUZBOS-CITAKDKDSA-N
InChIInChI=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
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 Nameacetoacetyl-coa
Chemical FormulaC25H40N7O18P3S
SMILESCC(=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
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • lipid particle
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
Ketone Body MetabolismPW002484 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
Steroid biosynthesisPW002482 ThumbThumb?image type=greyscaleThumb?image type=simple
Terpenoid backbone biosynthesisPW002485 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pyruvate metabolismec00620 Map00620
Steroid biosynthesisec00100 Map00100
Synthesis and degradation of ketone bodiesec00072 Map00072
Terpenoid backbone biosynthesisec00900 Map00900
Tryptophan metabolismec00380 Map00380
SMPDB Reactions
Acetyl-CoA ↔ Coenzyme A + acetoacetyl-CoA
3-Hydroxybutyryl-CoA + NAD ↔ acetoacetyl-CoA + NADH + hydron
Acetyl-CoA ↔ acetoacetyl-CoA + Coenzyme A
Acetyl-CoA + acetoacetyl-CoA + water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A
Acetoacetic acid + Succinyl-CoA ↔ Succinic acid + acetoacetyl-CoA
KEGG Reactions
Acetyl-CoA → acetoacetyl-CoA + Coenzyme A
3-Hydroxy-3-methylglutaryl-CoA + hydron + Coenzyme A ↔ Acetyl-CoA + water + acetoacetyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0004009000-9559fa356f1bae03b7caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0269300000-d5574d3fd84812c0057dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-05n1-0009600000-a29b94fc4d454c655babJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0001209000-21979fdba010c3871c5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0udi-0000000090-aa1f97ad009df4ad9439JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 57V, negativesplash10-0udi-0000100490-97b56edeb43a5d82ba85JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, negativesplash10-014i-0000910830-9d7a9bb5d2817f98fbf1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 93V, negativesplash10-0ar9-0101901000-ee3c1d5ebb3142f3c5afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 115V, negativesplash10-0a6r-5524900000-2d745cfa452462059e2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 136V, negativesplash10-056r-9513200000-037d88669e973d0dff1cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-004i-9400000000-fca9f3020e4e007e8164JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 187V, negativesplash10-004i-9300000000-13ad94b2682d99b6234dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 216V, negativesplash10-004i-9200000000-32dfa0b8d343e2eb7b7bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 260V, negativesplash10-004i-9100000000-6461ef6280ce0db781b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-014i-0000000900-727bb0c3c925e7bbeba4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00di-0190000000-0e093fb5398057b2093dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0900000000-b4c90f8c858e783159b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0udl-0018900000-91aaf6888a10aac16f57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00xr-0092000000-2dd3c44dfb7a39ee9a59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0670-0000904200-f3bcbcab3db17ae6a02aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00di-0190000000-3a982abdcfdcfe6b0420JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0udr-0027900000-0d41e18ae4bea1b5b7ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, positivesplash10-0002-6900000000-959cba779002108c94ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, positivesplash10-00di-9000000000-9fd58d8b09e3b71e5e6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 59V, positivesplash10-03di-0190000000-aa6e0456b3c35ec78a6aJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15345
HMDB IDHMDB01484
Pubchem Compound ID439214
Kegg IDC00332
ChemSpider ID24785115
FOODB IDFDB022648
WikipediaAcetoacetyl-CoA
BioCyc IDACETOACETYL-COA

Enzymes

Protein Details
1. Acetyl-CoA acetyltransferase
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of acetoacetyl-CoA in the biosynthesis of mevalonate, an intermediate required for the biosynthesis of sterols and nonsterol isoprenoids
Gene Name:
ERG10
Uniprot ID:
P41338
Molecular weight:
41728.39844
Reactions
2 acetyl-CoA → CoA + acetoacetyl-CoA.
Protein Details
2. Hydroxymethylglutaryl-CoA synthase
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:
ERG13
Uniprot ID:
P54839
Molecular weight:
55013.10156
Reactions
Acetyl-CoA + H(2)O + acetoacetyl-CoA → (S)-3-hydroxy-3-methylglutaryl-CoA + CoA.
Protein Details
3. 3-ketoacyl-CoA thiolase, peroxisomal
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA
Gene Name:
POT1
Uniprot ID:
P27796
Molecular weight:
44729.89844
Reactions
Acyl-CoA + acetyl-CoA → CoA + 3-oxoacyl-CoA.