Record Information
Version1.0
Creation Date2016-09-30 22:44:08 UTC
Update Date2020-05-21 16:28:08 UTC
BMDB IDBMDB0001322
Secondary Accession Numbers
  • BMDB01322
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 cattle, 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)); which is catalyzed by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In cattle, oleoyl-CoA is involved in the metabolic pathway called de novo triacylglycerol biosynthesis pathway.
Structure
Thumb
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]butanimidateHMDB
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]butanimidateHMDB
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 acidHMDB
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.17ALOGPS
logP1.13ChemAxon
logS-3.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4901020200-d927b9700b1f736673b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913140000-0c727433a1e07342d4f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010000-11cca0d7c51cc0c9c425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-9751431400-cae23b050bd3813947c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-5920210000-9e493a032128184122bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-a05d7d0eca3626435558View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Intestine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001322
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
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 ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Stearyl-CoA desaturase that utilizes O(2) and electrons from reduced cytochrome b5 to introduce the first double bond into saturated fatty acyl-CoA substrates. Catalyzes the insertion of a cis double bond at the delta-9 position into fatty acyl-CoA substrates including palmitoyl-CoA and stearoyl-CoA (By similarity). Gives rise to a mixture of 16:1 and 18:1 unsaturated fatty acids. Plays an important role in lipid biosynthesis. Plays an important role in regulating the expression of genes that are involved in lipogenesis and in regulating mitochondrial fatty acid oxidation (By similarity). Plays an important role in body energy homeostasis (By similarity). Contributes to the biosynthesis of membrane phospholipids, cholesterol esters and triglycerides (By similarity).
Gene Name:
SCD
Uniprot ID:
Q9TT94
Molecular weight:
41705.0
General function:
Energy production and conversion
Specific function:
Stearyl-CoA desaturase that utilizes O(2) and electrons from reduced cytochrome b5 to introduce the first double bond into saturated fatty acyl-CoA substrates. Catalyzes the insertion of a cis double bond at the delta-9 position into fatty acyl-CoA substrates including palmitoyl-CoA and stearoyl-CoA. Gives rise to a mixture of 16:1 and 18:1 unsaturated fatty acids.
Gene Name:
SCD5
Uniprot ID:
Q2KIA4
Molecular weight:
38215.0
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(14:0/14:0/0:0) + Oleoyl-CoA → TG(14:0/14:0/18:1(9Z)) + Coenzyme Adetails
DG(14:0/14:1(9Z)/0:0) + Oleoyl-CoA → TG(14:0/14:1(9Z)/18:1(9Z))[iso6] + Coenzyme Adetails
DG(14:0/15:0/0:0) + Oleoyl-CoA → TG(14:0/15:0/18:1(9Z)) + Coenzyme Adetails
DG(14:0/16:0/0:0) + Oleoyl-CoA → TG(14:0/16:0/18:1(9Z)) + Coenzyme Adetails
DG(14:0/18:0/0:0) + Oleoyl-CoA → TG(14:0/18:0/18:1(9Z))[iso6] + Coenzyme Adetails
DG(14:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(14:0/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(14:0/18:1(9Z)/18:1(9Z))[iso3] + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/14:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(14:1(9Z)/15:0/0:0) + Oleoyl-CoA → TG(14:1(9Z)/15:0/18:1(9Z)) + Coenzyme Adetails
DG(14:1(9Z)/16:0/0:0) + Oleoyl-CoA → TG(14:1(9Z)/16:0/18:1(9Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/16:1(9Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/16:1(9Z)/18:1(9Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + Oleoyl-CoA → TG(14:1(9Z)/18:0/18:1(9Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:1(11Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/18:1(9Z)/18:1(9Z))[iso3] + Coenzyme Adetails
DG(15:0/15:0/0:0) + Oleoyl-CoA → TG(15:0/15:0/18:1(9Z)) + Coenzyme Adetails
DG(15:0/16:0/0:0) + Oleoyl-CoA → TG(15:0/16:0/18:1(9Z))[iso6] + Coenzyme Adetails
DG(15:0/16:1(9Z)/0:0) + Oleoyl-CoA → TG(15:0/16:1(9Z)/18:1(9Z))[iso6] + Coenzyme Adetails
DG(15:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(15:0/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(15:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(15:0/18:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:0/16:0/0:0) + Oleoyl-CoA → TG(16:0/16:0/18:1(9Z)) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Oleoyl-CoA → TG(16:0/16:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:0/18:0/0:0) + Oleoyl-CoA → TG(16:0/18:0/18:1(9Z)) + Coenzyme Adetails
DG(16:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(16:0/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(16:0/18:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/16:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:0/18:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(11Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Oleoyl-CoA → TG(18:0/18:0/18:1(9Z)) + Coenzyme Adetails
DG(18:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(18:0/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(18:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(18:0/18:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(18:1(11Z)/18:1(11Z)/0:0) + Oleoyl-CoA → TG(18:1(11Z)/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(18:1(11Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(18:1(11Z)/18:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(18:1(9Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] + Coenzyme Adetails
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
Gene Name:
AGPAT1
Uniprot ID:
Q95JH2
Molecular weight:
32005.0
Reactions
LPA(16:0/0:0) + Oleoyl-CoA → Coenzyme A + PA(16:0/18:1(9Z))details
LPA(18:0/0:0) + Oleoyl-CoA → Coenzyme A + PA(18:0/18:1(9Z))details
LysoPA(18:1(11Z)/0:0) + Oleoyl-CoA → Coenzyme A + PA(18:1(11Z)/18:1(9Z))details
LysoPA(18:1(9Z)/0:0) + Oleoyl-CoA → Coenzyme A + PA(18:1(9Z)/18:1(9Z))details
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone (By similarity). Exhibits high acyl-CoA specificity for polyunsaturated fatty acyl-CoA, especially docosahexaenoyl-CoA (22:6-CoA, DHA-CoA) (By similarity).
Gene Name:
AGPAT4
Uniprot ID:
Q5E9R2
Molecular weight:
43907.0
Reactions
LPA(16:0/0:0) + Oleoyl-CoA → PA(16:0/18:1(9Z)) + Coenzyme Adetails
LPA(18:0/0:0) + Oleoyl-CoA → PA(18:0/18:1(9Z)) + Coenzyme Adetails
LysoPA(18:1(11Z)/0:0) + Oleoyl-CoA → PA(18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
LysoPA(18:1(9Z)/0:0) + Oleoyl-CoA → PA(18:1(9Z)/18:1(9Z)) + Coenzyme Adetails