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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:53 UTC
HMDB IDHMDB0001322
Secondary Accession Numbers
  • HMDB0006531
  • HMDB01322
  • HMDB06531
Metabolite Identification
Common NameOleoyl-CoA
DescriptionOleoyl-CoA belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Oleoyl-CoA is a strong basic compound (based on its pKa). Oleoyl-CoA exists in all living organisms, ranging from bacteria to humans. Within humans, oleoyl-CoA participates in a number of enzymatic reactions. In particular, oleoyl-CoA and glycerol 3-phosphate can be converted into lpa(18:1(9Z)/0:0); which is mediated by the enzyme glycerol-3-phosphate acyltransferase. In addition, lpa(18:1(9Z)/0:0) and oleoyl-CoA can be converted into PA(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In humans, oleoyl-CoA is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway.
Structure
Data?1563860693
Synonyms
ValueSource
Octadecenoyl-CoA (N-C18:1CoA)HMDB
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(9Z)-octadec-9-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidateGenerator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(9Z)-octadec-9-enoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidateGenerator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(9Z)-octadec-9-enoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acidGenerator
Chemical FormulaC39H68N7O17P3S
Average Molecular Weight1031.98
Monoisotopic Molecular Weight1031.360524011
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-[(9Z)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(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]oxyphosphonic acid
CAS Registry Number1716-06-9
SMILES
CCCCCCCC\C=C/CCCCCCCC(=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=C1N=CN=C2N
InChI Identifier
InChI=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
InChI KeyXDUHQPOXLUAVEE-ZXQNDDKTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability103.03 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4901020200-d927b9700b1f736673b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913140000-0c727433a1e07342d4f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010000-11cca0d7c51cc0c9c425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-9751431400-cae23b050bd3813947c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-5920210000-9e493a032128184122bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-a05d7d0eca3626435558Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Intestine
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022554
KNApSAcK IDNot Available
Chemspider ID4444057
KEGG Compound IDC00510
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6159
PubChem Compound5280355
PDB IDNot Available
ChEBI ID15534
Food Biomarker OntologyNot Available
VMH IDODECOA
References
Synthesis Referencenoue, Satoshi; Oba, Yuichi; Oga, Hajime. Manufacture of fatty acyl-coenzyme A using luciferase. Jpn. Kokai Tokkyo Koho (2004), 15 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kogushi M, Tanaka H, Kobayashi H, Yamada T, Ohtsuka I, Kimura T, Saito I: Effect of E5324, a novel inhibitor of acyl-CoA:cholesterol acyltransferase, on cholesteryl ester synthesis and accumulation in macrophages. Jpn J Pharmacol. 1995 Jun;68(2):191-9. [PubMed:7563976 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Terminal component of the liver microsomal stearyl-CoA desaturase system, that utilizes O(2) and electrons from reduced cytochrome b5 to catalyze the insertion of a double bond into a spectrum of fatty acyl-CoA substrates including palmitoyl-CoA and stearoyl-CoA.
Gene Name:
SCD
Uniprot ID:
O00767
Molecular weight:
41522.28
Reactions
Stearoyl-CoA + ferrocytochrome b5 + Oxygen + Hydrogen Ion → Oleoyl-CoA + ferricytochrome b5 + Waterdetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
BAAT
Uniprot ID:
Q14032
Molecular weight:
46298.865
General function:
Lipid transport and metabolism
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
ACOT7
Uniprot ID:
O00154
Molecular weight:
40454.945
Reactions
Oleoyl-CoA + Water → Coenzyme A + Oleic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
ACOT2
Uniprot ID:
P49753
Molecular weight:
53218.02
Reactions
Oleoyl-CoA + Water → Coenzyme A + Oleic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Molecular weight:
46326.09
Reactions
Oleoyl-CoA + Water → Coenzyme A + Oleic aciddetails
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
ACOT8
Uniprot ID:
O14734
Molecular weight:
35914.02
General function:
Involved in acyltransferase activity
Specific function:
Lysophoshatidylglycerol (LPG) specific acyltransferase that recognizes various acyl-CoAs and LPGs as substrates but demonstrates a clear preference for long chain saturated fatty acyl-CoAs and oleoyl-CoA as acyl donors. Prefers oleoyl-LPG over palmitoyl-LPG as an acyl receptor and oleoyl-CoA over lauroyl-CoA as an acyl donor
Gene Name:
LPGAT1
Uniprot ID:
Q92604
Molecular weight:
43089.1
General function:
Involved in stearoyl-CoA 9-desaturase activity
Specific function:
Fatty acid delta-9-desaturase that introduces a double bond in fatty acyl-coenzyme A at the delta-9 position.
Gene Name:
SCD5
Uniprot ID:
Q86SK9
Molecular weight:
37610.005
Reactions
Stearoyl-CoA + ferrocytochrome b5 + Oxygen + Hydrogen Ion → Oleoyl-CoA + ferricytochrome b5 + Waterdetails
General function:
Involved in acyltransferase activity
Specific function:
Acyl-CoA:lysocardiolipin acyltransferase. Possesses both lysophosphatidylinositol acyltransferase (LPIAT) and lysophosphatidylglycerol acyltransferase (LPGAT) activities. Recognizes both monolysocardiolipin and dilysocardiolipin as substrates with a preference for linoleoyl-CoA and oleoyl-CoA as acyl donors. Acts as a remodeling enzyme for cardiolipin, a major membrane polyglycerophospholipid. Converts lysophosphatidic acid (LPA) into phosphatidic acid (PA) with a relatively low activity. Required for establishment of the hematopoietic and endothelial lineages.
Gene Name:
LCLAT1
Uniprot ID:
Q6UWP7
Molecular weight:
44560.815
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Molecular weight:
46276.96
Reactions
Oleoyl-CoA + Water → Coenzyme A + Oleic aciddetails