Showing metabocard for Gamma-linolenoyl-CoA (BMDB0006368)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:51 UTC
Update Date2020-05-21 16:27:18 UTC
BMDB IDBMDB0006368
Secondary Accession Numbers
  • BMDB06368
Metabolite Identification
Common NameGamma-linolenoyl-CoA
DescriptionGamma-Linolenoyl-CoA, also known as gamolenoyl-CoA or gla-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, Gamma-linolenoyl-CoA is considered to be a fatty ester lipid molecule. Gamma-Linolenoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Gamma-Linolenoyl-CoA participates in a number of enzymatic reactions, within cattle. In particular, gamma-Linolenoyl-CoA and glycerol 3-phosphate can be converted into lpa(18:3(6Z,9Z,12Z)/0:0) through the action of the enzyme glycerol-3-phosphate acyltransferase. In addition, Lpa(18:3(6Z,9Z,12Z)/0:0) and gamma-linolenoyl-CoA can be converted into PA(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)); which is catalyzed by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In cattle, Gamma-linolenoyl-CoA is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6Z,9Z,12Z)-6,9,12-Octadecatrienoyl-CoAChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoyl-CoAChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoyl-coenzyme AChEBI
6-cis,9-cis,12-cis-Octadecatrienoyl-CoAChEBI
6-cis,9-cis,12-cis-Octadecatrienoyl-coenzyme AChEBI
gamma-Linolenoyl-coenzyme AChEBI
Gamolenoyl-CoAChEBI
GLA-CoAChEBI
g-Linolenoyl-coenzyme AGenerator
Γ-linolenoyl-coenzyme AGenerator
g-Linolenoyl-CoAGenerator
Γ-linolenoyl-CoAGenerator
Chemical FormulaC39H64N7O17P3S
Average Molecular Weight1027.948
Monoisotopic Molecular Weight1027.329223883
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-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Namegamma-linolenoyl-coa
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCC(=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=C(N)N=CN=C12
InChI Identifier
InChI=1S/C39H64N7O17P3S/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/h8-9,11-12,14-15,26-28,32-34,38,49-50H,4-7,10,13,16-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-,15-14-/t28-,32-,33-,34+,38-/m1/s1
InChI KeyXZQYPTBYQYZGRU-FHDVEODPSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.86ALOGPS
logP0.4ChemAxon
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 Count33ChemAxon
Refractivity249.2 m³·mol⁻¹ChemAxon
Polarizability100.2 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-4902020200-4de95c36351537daa2b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913140000-ea12377e23a82ea887f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010000-f2ad501225c5397aa66eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-9761432400-5ce6b84f01959faf46faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-4920211000-c0e97bd4a5f0953c565bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-5900100000-a93f68109e509d9a521aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-0e88eb5af01a59f2e7cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010201300-1632053287cc196307acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-5003302309-ad466ecefec128918a36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-bf36cba88177b2c29353View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000300688-0da593494ef1a0a1a809View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0100980000-057147a2c05e9d1955b3View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006368
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023905
KNApSAcK IDNot Available
Chemspider ID10140126
KEGG Compound IDC03035
BioCyc IDGAMMA-LINOLENOYL-COA
BiGG ID41063
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11966132
PDB IDNot Available
ChEBI ID15508
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Diacylglycerol O-acyltransferase 1
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) + Gamma-linolenoyl-CoA → TG(14:0/14:0/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/14:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/14:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/15:0/0:0) + Gamma-linolenoyl-CoA → TG(14:0/15:0/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/16:0/0:0) + Gamma-linolenoyl-CoA → TG(14:0/16:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(14:0/16:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/16:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/18:0/0:0) + Gamma-linolenoyl-CoA → TG(14:0/18:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(14:0/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/14:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/15:0/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/15:0/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/16:0/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/16:0/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/16:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/18:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(15:0/15:0/0:0) + Gamma-linolenoyl-CoA → TG(15:0/15:0/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails
DG(15:0/16:0/0:0) + Gamma-linolenoyl-CoA → TG(15:0/16:0/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(15:0/16:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(15:0/16:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(15:0/18:0/0:0) + Gamma-linolenoyl-CoA → TG(15:0/18:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(15:0/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(15:0/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(15:0/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(15:0/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(15:0/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(15:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) [iso6] + Coenzyme Adetails
DG(15:0/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(15:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:0/16:0/0:0) + Gamma-linolenoyl-CoA → TG(16:0/16:0/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/16:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:0/18:0/0:0) + Gamma-linolenoyl-CoA → TG(16:0/18:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:0/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:0/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:0/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:1(9Z)/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:0/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails
DG(18:0/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:0/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails
DG(18:1(11Z)/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(11Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:1(11Z)/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:1(11Z)/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(11Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:1(11Z)/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:1(9Z)/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails
DG(18:1(9Z)/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(18:1(9Z)/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails