3-oxohexacosanoyl-CoA (YMDB00960)

Identification
YMDB IDYMDB00960
Name3-oxohexacosanoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Oxohexacosyl-CoA, also known as 3-ketocerotoyl-CoA, belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group. Thus, 3-oxohexacosyl-CoA is considered to be a fatty ester lipid molecule. 3-Oxohexacosyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-oxohexacosanoyl-Coenzyme A
  • 3-Ketocerotoyl-CoA
  • 3-Ketohexacosanoyl-CoA
  • 3-Ketohexacosanoyl-coenzyme A
  • 3-Oxocerotoyl-CoA
CAS numberNot Available
WeightAverage: 1160.192
Monoisotopic: 1159.480639145
InChI KeyVOMUIFOBQMYJPJ-CPIGOPAHSA-N
InChIInChI=1S/C47H84N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-35(55)30-38(57)76-29-28-49-37(56)26-27-50-45(60)42(59)47(2,3)32-69-75(66,67)72-74(64,65)68-31-36-41(71-73(61,62)63)40(58)46(70-36)54-34-53-39-43(48)51-33-52-44(39)54/h33-34,36,40-42,46,58-59H,4-32H2,1-3H3,(H,49,56)(H,50,60)(H,64,65)(H,66,67)(H2,48,51,52)(H2,61,62,63)/t36-,40-,41-,42+,46-/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-oxohexacosanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name3-oxocerotoyl-coa
Chemical FormulaC47H84N7O18P3S
SMILESCCCCCCCCCCCCCCCCCCCCCCCC(=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 polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylphenols
Alternative Parents
Substituents
  • Polyterpenoid
  • 2-polyprenyl-6-methoxyphenol
  • Polyprenylphenol
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP4.39ALOGPS
logP4.38ChemAxon
logS-4.4ALOGPS
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 Count44ChemAxon
Refractivity283.35 m³·mol⁻¹ChemAxon
Polarizability122.31 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
  • endoplasmic reticulum
  • peroxisome
Organoleptic PropertiesNot Available
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
SMPDB Reactions
Tetracosanoyl-CoA + malonyl-CoA + hydron → Coenzyme A + Carbon dioxide + 3-oxohexacosanoyl-CoA
3-oxohexacosanoyl-CoA + hydron + NADPH → NADP + (3R)-hydroxyhexacosanoyl-CoA
KEGG Reactions
NAD + (S)-3-hydroxyhexacosanoyl-CoA ↔ NADH + hydron + 3-oxohexacosanoyl-CoA
Coenzyme A + 3-oxohexacosanoyl-CoA → Acetyl-CoA + Tetracosanoyl-CoA
NADPH + hydron + 3-oxohexacosanoyl-CoA ↔ NADP + (S)-3-hydroxyhexacosanoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900330100-9f06dc1ae1f3cc4107d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901522000-7a4ff45a78152f1f705dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900310000-52a8c4964c17c7926b22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05qc-2903131210-9c14f57b9bc484c8a408JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2901210000-ac5be58f1c6af5a00ceeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7900100000-f3f4638df7d404e92c87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-8cdd36ce8fec9a459b82JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-1900000120-7c5a95a156c523e676ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000149000-d162c165125574b822efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-6813d55e7aee02bbdd99JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-4900301230-c98b96a7eff75fc0f703JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05rc-4902300410-133a18d2ab1a96609e7fJSpectraViewer
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
  • Middleton, B. (1978). "3-Oxoacyl-coenzyme A thiolases and L-3-hydroxyacyl-coenzyme A dehydrogenases." Biochem Soc Trans 6:80-83.640209
  • Mathieu, M., Modis, Y., Zeelen, J. P., Engel, C. K., Abagyan, R. A., Ahlberg, A., Rasmussen, B., Lamzin, V. S., Kunau, W. H., Wierenga, R. K. (1997). "The 1.8 A crystal structure of the dimeric peroxisomal 3-ketoacyl-CoA thiolase of Saccharomyces cerevisiae: implications for substrate binding and reaction mechanism." J Mol Biol 273:714-728.9402066
  • 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 ID52977
HMDB IDHMDB0060241
Pubchem Compound ID25271602
Kegg IDNot Available
ChemSpider ID26333175
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Elongation of fatty acids protein 1
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).
Protein Details
2. 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.
Protein Details
3. Peroxisomal hydratase-dehydrogenase-epimerase
General function:
Involved in oxidoreductase activity
Specific function:
Second trifunctional enzyme acting on the beta-oxidation pathway for fatty acids, possessing hydratase-dehydrogenase- epimerase activities. Converts trans-2-enoyl-CoA via D-3- hydroxyacyl-CoA to 3-ketoacyl-CoA
Gene Name:
FOX2
Uniprot ID:
Q02207
Molecular weight:
98702.39844
Reactions
(3R)-3-hydroxyacyl-CoA → (2E)-2-enoyl-CoA + H(2)O.
(R)-3-hydroxyacyl-CoA + NAD(+) → 3-oxoacyl-CoA + NADH.
Protein Details
4. 3-oxoacyl-[acyl-carrier-protein] reductase
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.
Protein Details
5. 3-ketoacyl-CoA reductase
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.