Record Information
Version2.0
Creation Date2012-05-31 14:01:08 -0600
Update Date2015-06-03 15:54:34 -0600
Secondary Accession Numbers
  • ECMDB03943
Identification
Name:3-Oxohexanoyl-CoA
Description3-Oxohexanoyl-CoA is an intermediate in Fatty acid elongation. 3-Oxohexanoyl-CoA is the 3rd to last step in the synthesis of Hexanoyl-CoA and is converted from Butanoyl-CoA via the enzyme acetyl-CoA acyltransferase 2 (EC 2.3.1.16). It is then converted to (S)-Hydroxyhexanoyl-CoA via the 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35).
Structure
Thumb
Synonyms:
  • β-hexanoyl-CoA
  • 3-Ketohexanoyl CoA.
  • 3-Ketohexanoyl Coenzyme A.
  • 3-Ketohexanoyl-CoA
  • 3-Oxohexanoyl-CoA
  • 3-Oxohexanoyl-Coenzyme A
  • b-Hexanoyl-CoA
  • Beta-Hexanoyl-CoA
  • Ketohexanoyl-CoA
  • Ketohexanoyl-Coenzyme A
  • Ketohexanoyl-coenzyme-A
  • β-Hexanoyl-CoA
Chemical Formula:C27H44N7O18P3S
Weight:Average: 879.661
Monoisotopic: 879.167637865
InChI Key:NFOYYXQAVVYWKV-ZOGSZLKASA-N
InChI:InChI=1S/C27H44N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-14,16,20-22,26,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t16-,20-,21-,22?,26-/m1/s1
CAS number:19774-86-8
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-oxohexanoyl)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-oxohexanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
SMILES:CCCC(=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=C(N)N=CN=C12
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-oxo-acyl CoAs
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-3.064PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.43 g/LALOGPS
logP-0.04ALOGPS
logP-5.6ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity191.33 m³·mol⁻¹ChemAxon
Polarizability77.82 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Fatty acid metabolismPW000796 ThumbThumb?image type=greyscaleThumb?image type=simple
fatty acid oxidation (hexanoate)PW001019 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1901000120-68f6500665ed8e511dc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0912000000-54a826f27a4c6ba4efb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-0fb092f4177cad6035baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u0-4911030340-b74454836fd5a8474037View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3910110010-eb4a9cd58caa577306dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-70d1d4cf63d535a9c95cView in MoNA
References
References:
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27648
HMDB IDHMDB03943
Pubchem Compound ID440610
Kegg IDC05269
ChemSpider ID389508
Wikipedia IDNot Available
BioCyc IDK-HEXANOYL-COA
EcoCyc IDK-HEXANOYL-COA

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 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.