α-linolenoyl-CoA (PAMDB120004)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120004
Identification
Name: α-linolenoyl-CoA
Description:An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of α-linolenic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (9Z,12Z,15Z)-9,12,15-octadecatrienoyl-CoA
  • (9Z,12Z,15Z)-9,12,15-octadecatrienoyl-coenzyme A
  • (9Z,12Z,15Z)-Octadecatrienoyl-CoA
  • (Z,Z,Z)-9,12,15-octadecatrienoyl-CoA
  • (Z,Z,Z)-9,12,15-octadecatrienoyl-coenzyme A
  • (Z,Z,Z)-octadeca-9,12,15-trienoyl-CoA
  • (Z,Z,Z)-octadeca-9,12,15-trienoyl-coenzyme A
  • all-cis-9,12,15-octadecatrienoyl-CoA
  • all-cis-9,12,15-octadecatrienoyl-coenzyme A
  • alpha-Linolenoyl-CoA
  • α-linolenoyl-coenzyme A
Chemical Formula: C39H60N7O17P3S
Average Molecular Weight: 1023.921
Monoisotopic Molecular Weight: 1027.3292
InChI Key: OMKFKBGZHNJNEX-KZWMEWPFSA-J
InChI: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/h5-6,8-9,11-12,26-28,32-34,38,49-50H,4,7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/p-4/b6-5-,9-8-,12-11-/t28-,32+,33+,34?,38-/m0/s1
CAS number: Not Available
IUPAC Name:3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(9Z,12Z,15Z)-octadeca-6,12,15-trienoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}
Traditional IUPAC Name: [(2R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
SMILES:CCC=CCC=CCC=CCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OCC3(OC(N2(C=NC1(C(N)=NC=NC=12)))C(O)C(OP(=O)([O-])[O-])3)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Long-chain fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.84 mg/mLALOGPS
logP2.84ALOGPS
logP-0.69ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count33ChemAxon
Refractivity249.2 m3·mol-1ChemAxon
Polarizability98.62 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
ATP + α-linolenate + coenzyme A → α-linolenoyl-CoA + diphosphate + AMP
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Clouet P, Niot I, Bézard J (1989)Pathway of alpha-linolenic acid through the mitochondrial outer membrane in the rat liver and influence on the rate of oxidation. Comparison with linoleic and oleic acids. The Biochemical journal 263, Pubmed: 2597132
    • Ichihara K, Suda Y (2003)Lipid biosynthesis in developing perilla seeds. Phytochemistry 63, Pubmed: 12711134
    • Meng W, Su YC, Saunders RM, Chye ML (2011)The rice acyl-CoA-binding protein gene family: phylogeny, expression and functional analysis. The New phytologist 189, Pubmed: 21128943
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC51985
    HMDBHMDB06290
    CHEBI51985
    PUBCHEM49859601
    LIGAND-CPDC16162