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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 02:41:36 UTC
Update Date2021-09-14 15:45:05 UTC
HMDB IDHMDB0006368
Secondary Accession Numbers
  • HMDB06368
Metabolite Identification
Common NameGamma-linolenoyl-CoA
DescriptionGamma-linolenoyl-CoA is the product of a chemical reaction that involves linoleoyl-CoA desaturase which acts as a catalyst. In enzymology, linoleoyl-CoA desaturase (EC 1.14.19.3) is an enzyme that catalyzes the chemical reaction. linoleoyl-CoA + AH2 + O2 gamma-linolenoyl-CoA + A + 2 H2O. The 3 substrates of this enzyme are linoleoyl-CoA, AH2, and O2, whereas its 3 products are gamma-linolenoyl-CoA, A, and H2O. (Wikipedia).
Structure
Data?1582752382
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.84 g/LALOGPS
logP10(2.86) g/LALOGPS
logP10(0.4) g/LChemAxon
logS10(-3.1) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 10V, Positive-QTOFsplash10-000i-4902020200-4de95c36351537daa2b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 20V, Positive-QTOFsplash10-000i-1913140000-ea12377e23a82ea887f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 40V, Positive-QTOFsplash10-000i-1900010000-f2ad501225c5397aa66e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 10V, Negative-QTOFsplash10-0a7i-9761432400-5ce6b84f01959faf46fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 20V, Negative-QTOFsplash10-0560-4920211000-c0e97bd4a5f0953c565b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 40V, Negative-QTOFsplash10-0a7i-5900100000-a93f68109e509d9a521a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 10V, Negative-QTOFsplash10-004i-9000000000-0e88eb5af01a59f2e7cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 20V, Negative-QTOFsplash10-004i-9010201300-1632053287cc196307ac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 40V, Negative-QTOFsplash10-004j-5003302309-ad466ecefec128918a362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 10V, Positive-QTOFsplash10-004i-9000000000-bf36cba88177b2c293532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 20V, Positive-QTOFsplash10-03di-9000300688-0da593494ef1a0a1a8092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenoyl-CoA 40V, Positive-QTOFsplash10-00di-0100980000-057147a2c05e9d1955b32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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
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
Food Biomarker OntologyNot Available
VMH IDLNLNCGCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

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
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic 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
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic 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
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic 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 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
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic aciddetails