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oleoyl-CoA (YMDB00539)

Identification
YMDB IDYMDB00539
Nameoleoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionOleoyl-CoA, also known as oleoyl-coenzyme A or S-oleoyl-CoA, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Thus, oleoyl-CoA is considered to be a fatty ester lipid molecule. Oleoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Oleoyl-Coa
  • (9Z)-Octadec-9-enoyl-CoA
  • (9Z)-Octadec-9-enoyl-coenzyme A
  • (9Z)-Octadecenoyl-CoA
  • cis-9-Octadecenoyl-CoA
  • cis-9-Octadecenoyl-coenzyme A
  • Oleoyl-coenzyme A
  • S-[(9Z)-Octadec-9-enoyl]-CoA
  • S-[(9Z)-Octadec-9-enoyl]-coenzyme A
  • S-Oleoyl-CoA
  • S-Oleoylcoenzyme A
  • Oleyl-coenzyme A
  • Oleyl-CoA
  • 9-Octadecenoyl-CoA
  • 9-Octadecenoyl-coenzyme A
  • Coenzyme A cis-9-octadecenoate
  • Coenzyme A oleate
  • Oleoyl coenzyme A
  • Oleyl coenzyme A
CAS number1716-06-9
WeightAverage: 1031.98
Monoisotopic: 1031.360524011
InChI KeyXDUHQPOXLUAVEE-BPMMELMSSA-N
InChIInChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b12-11-/t28-,32-,33-,34+,38-/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-[(9Z)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Nameoleoyl-CoA
Chemical FormulaC39H68N7O17P3S
SMILESCCCCCCCC\C=C/CCCCCCCC(=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 fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a 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 fatty acyl 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
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • 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
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP2.83ALOGPS
logP1.13ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity246.97 m³·mol⁻¹ChemAxon
Polarizability104.05 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
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerol metabolismPW002407 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
SMPDB Reactions
Glycerol 3-phosphate + oleoyl-CoA → Coenzyme A + 1-oleyl-2-lyso-phosphatidate
Glycerone phosphate + oleoyl-CoA → Coenzyme A + 1-oleoyl-2-lyso-glycerone phosphate
oleoyl-CoA + 1-oleyl-2-lyso-phosphatidate → Coenzyme A + PA(18:1(9Z)/18:1(9Z))
KEGG Reactions
episterol + oleoyl-CoA ↔ episteryl oleate + Coenzyme A
ergosterol + oleoyl-CoA ↔ ergosteryl oleate + Coenzyme A
24-methylidene-5alpha-cholest-8-en-3beta-ol + oleoyl-CoA ↔ fecosteryl oleate + Coenzyme A
oleoyl-CoA + Lanosterin ↔ Coenzyme A + lanosteryl oleate
zymosterol + oleoyl-CoA ↔ zymosteryl oleate + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-4906410200-1899315eb4219b9dde62JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-1917220000-cb0baa3e5a11f9502e76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1903100000-27f4745a14c8e5b0a42cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-9640332400-9c29424b2af433de71f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910211000-1e669ef968f018efb78eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7900000000-2230a3119b1d85b27bceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-bce9fa50c22d56521761JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-6900200547-73501c099b9a3879e08cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100790000-19a94a35d29dd21132f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-0afd0bffa1bd09c6b53cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-9010201300-979386e6895924e3373cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-9103400305-4e40566cb9d89b6ca5deJSpectraViewer
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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Geisbrecht, B. V., Zhu, D., Schulz, K., Nau, K., Morrell, J. C., Geraghty, M., Schulz, H., Erdmann, R., Gould, S. J. (1998). "Molecular characterization of Saccharomyces cerevisiae Delta3, Delta2-enoyl-CoA isomerase." J Biol Chem 273:33184-33191.9837886
  • Zweytick, D., Leitner, E., Kohlwein, S. D., Yu, C., Rothblatt, J., Daum, G. (2000). "Contribution of Are1p and Are2p to steryl ester synthesis in the yeast Saccharomyces cerevisiae." Eur J Biochem 267:1075-1082.10672016
Synthesis Reference:noue, Satoshi; Oba, Yuichi; Oga, Hajime. Manufacture of fatty acyl-coenzyme A using luciferase. Jpn. Kokai Tokkyo Koho (2004), 15 pp.
External Links:
ResourceLink
CHEBI ID15534
HMDB IDHMDB01322
Pubchem Compound ID439247
Kegg IDC00510
ChemSpider ID24808243
FOODB IDFDB022554
Wikipedia IDNot Available
BioCyc IDOLEOYL-COA

Enzymes

Protein Details
1. Long-chain-fatty-acid--CoA ligase 4
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Contributes, with FAA1, to the activation of imported myristate
Gene Name:
FAA4
Uniprot ID:
P47912
Molecular weight:
77266.5
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
Protein Details
2. Acyl-coenzyme A oxidase
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Acyl-CoA + O(2) = trans-2,3-dehydroacyl-CoA + H(2)O(2)
Gene Name:
POX1
Uniprot ID:
P13711
Molecular weight:
84041.39844
Reactions
Acyl-CoA + O(2) → trans-2,3-dehydroacyl-CoA + H(2)O(2).
Protein Details
3. Long-chain-fatty-acid--CoA ligase 1
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It may supplement intracellular myristoyl-CoA pools from exogenous myristate. Preferentially acts on C12:0-C16:0 fatty acids with myristic and pentadecanic acid (C15:0) having the highest activities
Gene Name:
FAA1
Uniprot ID:
P30624
Molecular weight:
77865.79688
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
Protein Details
4. Long-chain-fatty-acid--CoA ligase 3
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. This enzyme acts preferentially on C16 and C18 fatty acids with a cis-double bond at C-9-C-10
Gene Name:
FAA3
Uniprot ID:
P39002
Molecular weight:
77946.0
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
Protein Details
5. Probable 1-acyl-sn-glycerol-3-phosphate acyltransferase
General function:
Involved in acyltransferase activity
Specific function:
May be an acyltransferase with an altered substrate specificity that enables it to use a C-26-CoA in place of the C-16 or C-18-CoAs used by the wild-type protein
Gene Name:
SLC1
Uniprot ID:
P33333
Molecular weight:
33886.69922
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Protein Details
6. Glycerol-3-phosphate O-acyltransferase 1
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT1
Uniprot ID:
P32784
Molecular weight:
85693.5
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
Protein Details
7. Sterol O-acyltransferase 2
General function:
Involved in O-acyltransferase activity
Specific function:
Ensures probably most of the acyltransferase activity. Suppression of ARE2 reduces sterol ester levels to 25% of the normal value
Gene Name:
ARE2
Uniprot ID:
P53629
Molecular weight:
74022.20313
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
Protein Details
8. Sterol O-acyltransferase 1
General function:
Involved in O-acyltransferase activity
Specific function:
Acyl-CoA + cholesterol = CoA + cholesterol ester
Gene Name:
ARE1
Uniprot ID:
P25628
Molecular weight:
71612.5
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
Protein Details
9. Glycerol-3-phosphate O-acyltransferase 2
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT2
Uniprot ID:
P36148
Molecular weight:
83644.0
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
Protein Details
10. Lysophospholipid acyltransferase
General function:
Involved in 1-acylglycerol-3-phosphate O-acyltransferas
Specific function:
Membrane-bound O-acyltransferase that mediates the incorporation of unsaturated acyl chains into the sn-2 position of phopholipids. Preferentially acylates lysophosphocholine, but also lysophosphoethanolamine and lysophosphatidylglycerol
Gene Name:
ALE1
Uniprot ID:
Q08548
Molecular weight:
72227.39844
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphocholine → CoA + 1,2-diacyl-sn-glycero-3-phosphocholine.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphoethanolamine → CoA + 1,2-diacyl-sn-glycero-3-phosphoethanolamine.
Protein Details
11. Acyl-CoA desaturase 1
General function:
Involved in stearoyl-CoA 9-desaturase activity
Specific function:
Utilizes O(2) and electrons from the reduced cytochrome b(5) domain to catalyze the insertion of a double bond into a spectrum of fatty acyl-CoA substrates (Probable)
Gene Name:
OLE1
Uniprot ID:
P21147
Molecular weight:
58402.60156
Reactions
Stearoyl-CoA + 2 ferrocytochrome b5 + O(2) + 2 H(+) → oleoyl-CoA + 2 ferricytochrome b5 + 2 H(2)O.
Protein Details
12. Lipase 5
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL5
Uniprot ID:
Q12043
Molecular weight:
84715.10156
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
13. Lipase 4
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL4
Uniprot ID:
P36165
Molecular weight:
102716.0
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
14. Lysophosphatidic acid:oleoyl-CoA acyltransferase 1
General function:
lipid particle organization
Specific function:
Acyl-CoA-dependent lysophosphatidic acid acyltransferase with preference for oleoyl-CoA. Involved in triacylglyceride homeostasis and lipid droplet formation. Involved in vacuolar protein sorting.
Gene Name:
LOA1
Uniprot ID:
Q06508
Molecular weight:
33815.635
Reactions

Transporters

Protein Details
1. Peroxisomal long-chain fatty acid import protein 1
General function:
Involved in transport
Specific function:
Involved in the import of activated long-chain fatty acids from the cytosol to the peroxisomal matrix
Gene Name:
PXA2
Uniprot ID:
P34230
Molecular weight:
97125.29688