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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:51:25 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006290
Secondary Accession Numbers
  • HMDB06290
Metabolite Identification
Common NameAlpha-Linolenoyl-CoA
DescriptionAlpha-Linolenoyl-CoA, also known as a-linolenoyl-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. Alpha-Linolenoyl-CoA is a strong basic compound (based on its pKa).
Structure
Data?1582752379
Synonyms
ValueSource
a-Linolenoyl-CoAGenerator
Α-linolenoyl-CoAGenerator
(9Z,12Z,15Z)-Octadecatrienoyl-CoAHMDB
(9Z,12Z,15Z)-Octadecatrienoyl-coenzyme AHMDB
alpha-Linolenoyl-coenzyme AHMDB
Chemical FormulaC39H64N7O17P3S
Average Molecular Weight1027.948
Monoisotopic Molecular Weight1027.329223883
IUPAC Name{[(2R,4S,5R)-5-(6-amino-9H-purin-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}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional 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}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H]([C@@H](O)C1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N
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/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)/b6-5-,9-8-,12-11-/t28-,32+,33?,34+,38-/m1/s1
InChI KeyOMKFKBGZHNJNEX-QJTDXEISSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.84 g/LALOGPS
logP2.84ALOGPS
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
Polarizability97.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+279.58930932474
DeepCCS[M-H]-277.93430932474
DeepCCS[M-2H]-312.12630932474
DeepCCS[M+Na]+285.74630932474
AllCCS[M+H]+297.232859911
AllCCS[M+H-H2O]+297.832859911
AllCCS[M+NH4]+296.732859911
AllCCS[M+Na]+296.532859911
AllCCS[M-H]-306.032859911
AllCCS[M+Na-2H]-312.332859911
AllCCS[M+HCOO]-319.132859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-01p9-0008009000-b19fa83af4283fcd0b892020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-05n0-0009600000-078cbf77a2f434cd44ed2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-03di-0019002000-1380de023ce360bf7ec02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-0a4i-0279310000-44bf2f31c6db5988d5a72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-004j-0002149000-861577e53f84f4b2ebb92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-01ot-0002289000-ffe3ffa5e78e22454bca2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 71V, negative-QTOFsplash10-004i-9000200000-3cecb69b68b6f9ff81842020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 84V, negative-QTOFsplash10-056r-7000900000-3d284b943b5b0ebb41bb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 94V, negative-QTOFsplash10-056r-1000900000-34703ef6e109c21c18e92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 104V, negative-QTOFsplash10-056r-1000901000-acb57860a878dcc2023d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 125V, negative-QTOFsplash10-0a6r-1211901000-cc5cc6376dc63c7e796b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 156V, negative-QTOFsplash10-056r-9833500000-3f06d96e6b56a1c533b82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 189V, negative-QTOFsplash10-004i-9511000000-856cf20e875260148ebb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 230V, negative-QTOFsplash10-004i-9400000000-10c923a4025dad9a24ec2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA Orbitrap 273V, negative-QTOFsplash10-004i-9300000000-17dbaea3bd39295e9b7d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-004j-1000319013-26b2710bf282ad4e0efc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-00di-0190000000-a3b560dd23c1d54b07402020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-0a4i-0900000000-55f0257dfa1a12894fde2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl-CoA n/a 71V, negative-QTOFsplash10-052r-0019000000-2a83d907ab00b91dacc62020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl-CoA 10V, Positive-QTOFsplash10-000i-3902020200-1184da02054c79f7d9432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl-CoA 20V, Positive-QTOFsplash10-000i-1913140000-f435f6bf9df881a42e1b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl-CoA 40V, Positive-QTOFsplash10-000i-1900010000-a3a909bd9837261df0e12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl-CoA 10V, Negative-QTOFsplash10-0a7i-9761432401-fd1bbec725c99dd870632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl-CoA 20V, Negative-QTOFsplash10-053r-4920210000-58e825fa745dd2fb57252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl-CoA 40V, Negative-QTOFsplash10-0a7i-5900100000-c18f0f871cf87bcf5fa92017-09-01Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
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 IDFDB023879
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16162
BioCyc IDNot Available
BiGG ID2218410
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477815
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDLNLNCACOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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
Alpha-Linolenoyl-CoA + Water → Coenzyme A + alpha-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
Alpha-Linolenoyl-CoA + Water → Coenzyme A + alpha-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
Alpha-Linolenoyl-CoA + Water → Coenzyme A + alpha-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
Alpha-Linolenoyl-CoA + Water → Coenzyme A + alpha-Linolenic aciddetails