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Human Metabolome Database Version 3.5

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Showing metabocard for Alpha-Linolenoyl-CoA (HMDB06290)

Record Information
Version 3.5
Creation Date 2007-05-22 15:51:25 -0600
Update Date 2013-02-08 17:14:44 -0700
HMDB ID HMDB06290
Secondary Accession Numbers None
Metabolite Identification
Common Name Alpha-Linolenoyl-CoA
Description Alpha-Linolenoyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. alpha-Linolenoyl-CoA is converted. from Linoleoyl-CoA via the enzyme fatty acid desaturase (EC 1.14.19.-). It is then converted to alpha-Linolenic acid via the enzyme palmitoyl-CoA hydrolase(EC 3.1.2.2).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (9Z,12Z,15Z)-Octadecatrienoyl-CoA
  2. (9Z,12Z,15Z)-Octadecatrienoyl-Coenzyme A
  3. alpha-Linolenoyl-CoA
  4. alpha-Linolenoyl-Coenzyme A
Chemical Formula C39H64N7O17P3S
Average Molecular Weight 1027.948
Monoisotopic Molecular Weight 1027.329223883
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 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
CAS Registry Number Not 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 Key OMKFKBGZHNJNEX-QJTDXEISSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.84 g/L ALOGPS
LogP 2.84 ALOGPS
LogP -0.69 ChemAxon
LogS -3.09 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 17 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 363.63 A2 ChemAxon
Rotatable Bond Count 33 ChemAxon
Refractivity 249.2 ChemAxon
Polarizability 98.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023879
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C16162 Link_out
BioCyc ID Not Available
BiGG ID 2218410 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06290 Link_out
Metagene Link HMDB06290 Link_out
METLIN ID Not Available
PubChem Compound 53477815 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Bile acid-CoA:amino acid N-acyltransferase
Reactions: Not Available
Gene Name: BAAT
Uniprot ID: Q14032 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic acyl coenzyme A thioester hydrolase
Reactions:
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic acid details
Gene Name: ACOT7
Uniprot ID: O00154 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 2, mitochondrial
Reactions:
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic acid details
Gene Name: ACOT2
Uniprot ID: P49753 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 4
Reactions:
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic acid details
Gene Name: ACOT4
Uniprot ID: Q8N9L9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 8
Reactions: Not Available
Gene Name: ACOT8
Uniprot ID: O14734 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 1
Reactions:
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic acid details
Gene Name: ACOT1
Uniprot ID: Q86TX2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA