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3-Oxooctadecanoyl-CoA (M2MDB001579)

Record Information
Version2.0
Creation Date2012-07-30 14:54:44 -0600
Update Date2015-09-17 15:41:19 -0600
Secondary Accession Numbers
  • ECMDB21170
Identification
Name:3-Oxooctadecanoyl-CoA
Description3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid}
  • 3-Ketostearoyl-coa
  • 3-Ketostearoyl-coenzyme A
  • 3-Oxooctadecanoyl-CoA
  • 3-Oxooctadecanoyl-coenzyme A
  • 3-Oxostearoyl-CoA
  • 3-Oxostearoyl-Coenzyme A
  • b-Ketostearoyl-CoA
  • b-Ketostearoyl-coenzyme A
  • Beta-Ketostearoyl-CoA
  • Beta-Ketostearoyl-Coenzyme A
  • β-Ketostearoyl-CoA
  • β-Ketostearoyl-coenzyme A
Chemical Formula:C39H66N7O18P3S
Weight:Average: 1045.964
Monoisotopic: 1045.339788569
InChI Key:LGOGWHDPDVAUNY-LFZQUHGESA-L
InChI:InChI=1S/C39H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-2/t28-,32-,33-,34+,38-/m1/s1
CAS number:86370-20-9
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-oxooctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:3-oxooctadecanoyl-coa
SMILES:CCCCCCCCCCCCCCCC(=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 long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 3-oxoacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • 1,3-dicarbonyl compound
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Ketone
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP2.43ALOGPS
logP0.82ChemAxon
logS-2.8ALOGPS
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 Count36ChemAxon
Refractivity246.54 m³·mol⁻¹ChemAxon
Polarizability105.18 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-Oxooctadecanoyl-CoA + Coenzyme A <> Acetyl-CoA + Palmityl-CoA
3-Oxooctadecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxyoctadecanoyl-CoA + NAD
3-Oxooctadecanoyl-CoA + NADPH + Hydrogen ion <> 3-Hydroxyoctadecanoyl-CoA + NADP
(S)-3-Hydroxyoctadecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxooctadecanoyl-CoA + 3-Oxooctadecanoyl-CoA
3-Oxooctadecanoyl-CoA + Coenzyme A + 3-Oxooctadecanoyl-CoA > Acetyl-CoA + Stearoyl-CoA + Stearoyl-CoA
SMPDB Pathways:
fatty acid oxidation (steareate)PW001024 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4901020100-42e12c9443811aa9b23aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0922130000-507f0cf5c97de000bbd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000100-92fc72df57fb89aa8c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-9661331400-f14ff1dd26fae045a551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4920200000-f6293880f1450083d4cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-7900000000-23f4e90322bfc73a51a5View in MoNA
References
References:
  • Nagao, M., Ishibashi, T., Okayasu, T., Imai, Y. (1983). "Possible involvement of NADPH-cytochrome P450 reductase and cytochrome b5 on beta-ketostearoyl-CoA reduction in microsomal fatty acid chain elongation supported by NADPH." FEBS Lett 155:11-14. Pubmed: 6404652
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID50571
HMDB IDHMDB06498
Pubchem Compound ID23724660
Kegg IDC16216
ChemSpider ID21865760
Wikipedia IDNot Available
BioCyc IDCPD-10260
EcoCyc IDCPD-10260

Enzymes

Protein Details
1. 3-oxoacyl-[acyl-carrier-protein] reductase
General function:
Involved in 3-oxoacyl-[acyl-carrier-protein] reductase (NADPH) activity
Specific function:
(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) = 3-oxoacyl-[acyl-carrier-protein] + NADPH
Gene Name:
fabG
Uniprot ID:
P0AEK2
Molecular weight:
25560
Reactions
(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) = 3-oxoacyl-[acyl-carrier-protein] + NADPH.
Protein Details
2. 3-ketoacyl-CoA thiolase
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.
Protein Details
3. Fatty acid oxidation complex subunit alpha
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.
Protein Details
4. Probable enoyl-CoA hydratase paaF
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.
Protein Details
5. 3-ketoacyl-CoA thiolase_
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.
Protein Details
6. Fatty acid oxidation complex subunit alpha_
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.

Transporters

Protein Details
1. Fatty acid oxidation complex subunit alpha
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.