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Identification
YMDB IDYMDB00733
Name3-oxodocosanoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Oxodocosanoyl-CoA, also known as 3-keto-C22-CoA or 3-ketobehenoyl-CoA, belongs to the class of organic compounds known as very-long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 22 carbon atoms or more. Thus, 3-oxodocosanoyl-CoA is considered to be a fatty ester lipid molecule. 3-Oxodocosanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • 3-keto-C22-CoA
  • 3-ketodocosanoyl-CoA
  • 3-ketodocosanoyl-coenzyme A
  • 3-oxodocosanoyl-coenzyme A
  • 3-Ketobehenoyl-CoA
  • 3-Oxobehenoyl-CoA
  • 3-Oxobehenoyl-coenzyme A
CAS numberNot Available
WeightAverage: 1104.086
Monoisotopic: 1103.418038889
InChI KeyRKCOGGUHKPTOQJ-GNSUAQHMSA-N
InChIInChI=1S/C43H76N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-31(51)26-34(53)72-25-24-45-33(52)22-23-46-41(56)38(55)43(2,3)28-65-71(62,63)68-70(60,61)64-27-32-37(67-69(57,58)59)36(54)42(66-32)50-30-49-35-39(44)47-29-48-40(35)50/h29-30,32,36-38,42,54-55H,4-28H2,1-3H3,(H,45,52)(H,46,56)(H,60,61)(H,62,63)(H2,44,47,48)(H2,57,58,59)/t32-,36-,37-,38+,42-/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-oxodocosanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name3-keto-C22-coa
Chemical FormulaC43H76N7O18P3S
SMILESCCCCCCCCCCCCCCCCCCCC(=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 very-long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 22 carbon atoms or more.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentVery-long-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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
logP3.43ALOGPS
logP2.6ChemAxon
logS-3.4ALOGPS
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 Count40ChemAxon
Refractivity264.95 m³·mol⁻¹ChemAxon
Polarizability113.67 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (docosanoyl)PW002408 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA)PW002404 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
SMPDB Reactions
Eicosanoyl-CoA + malonyl-CoA + hydronCoenzyme A + Carbon dioxide + 3-oxodocosanoyl-CoA
3-oxodocosanoyl-CoA + hydron + NADPHNADP + (3R)-3-hydroxy-docosanoyl-CoA
KEGG Reactions
NADPH + hydron + 3-oxodocosanoyl-CoANADP + 3-hydroxydocosanoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-6906141400-d62e410881aa05cbd42dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5911210100-578bcad406850cb9ca00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-8900100000-369f5484d0e99c477461JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4901810200-04d1a1764224605f35f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1911820000-2ad808781edf76eda700JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900400000-ebefcbce21561bafb2d5JSpectraViewer
References
References:
  • 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
  • Han, G., Gable, K., Kohlwein, S. D., Beaudoin, F., Napier, J. A., Dunn, T. M. (2002). "The Saccharomyces cerevisiae YBR159w gene encodes the 3-ketoreductase of the microsomal fatty acid elongase." J Biol Chem 277:35440-35449.12087109
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID52328
HMDB IDHMDB0060215
Pubchem Compound ID25229584
Kegg IDNot Available
ChemSpider ID21866049
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in fatty acid elongase activity
Specific function:
May be a membrane bound enzyme involved in the highly specific elongation of saturated 14-carbon fatty acids (14:0) to 16-carbon species (16:0)
Gene Name:
ELO1
Uniprot ID:
P39540
Molecular weight:
36233.60156
Reactions
Acyl-CoA + malonyl-CoA → 3-oxoacyl-CoA + CoA + CO(2).
General function:
Involved in oxidoreductase activity
Specific function:
Involved in biosynthesis of fatty acids in mitochondria
Gene Name:
OAR1
Uniprot ID:
P35731
Molecular weight:
31183.69922
Reactions
(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) → 3-oxoacyl-[acyl-carrier-protein] + NADPH.
General function:
Involved in oxidoreductase activity
Specific function:
Component of the microsomal membrane bound fatty acid elongation system, which produces the 26-carbon very long-chain fatty acids (VLCFA) from palmitate. Catalyzes the reduction of the 3-ketoacyl-CoA intermediate that is formed in each cycle of fatty acid elongation. VLCFAs serve as precursors for ceramide and sphingolipids
Gene Name:
IFA38
Uniprot ID:
P38286
Molecular weight:
38707.80078
Reactions
3-hydroxyacyl-CoA + NADP(+) → 3-oxoacyl-CoA + NADPH.