Record Information
Version1.0
Creation Date2016-09-30 23:08:56 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0004258
Secondary Accession Numbers
  • BMDB04258
Metabolite Identification
Common NameEicosanoyl-CoA
DescriptionEicosanoyl-CoA, also known as S-eicosanoate or arachidinoyl-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. Eicosanoyl-CoA is a strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
Arachidinoyl-CoAHMDB
Arachidinoyl-coenzyme AHMDB
Arachidoyl coenzyme AHMDB
Arachidoyl-CoAHMDB
Arachidoyl-coenzyme AHMDB
Arachidyl CoAHMDB
Arachidyl coenzyme AHMDB
EicosanethioateHMDB
Eicosanethioic acidHMDB
Eicosanethioic acid S-ester with coenzyme AHMDB
Eicosanoyl coenzyme AHMDB
Eicosyl-coenzyme AHMDB
Icosanoyl-CoAHMDB
S-EicosanoateHMDB
S-Eicosanoate CoAHMDB
S-Eicosanoate coenzyme AHMDB
S-Eicosanoic acidHMDB
Chemical FormulaC41H74N7O17P3S
Average Molecular Weight1062.049
Monoisotopic Molecular Weight1061.407474203
IUPAC Name(2R)-4-({[({[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-(icosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid
Traditional Name(2R)-4-[({[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-(2-{[2-(icosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid
CAS Registry Number15895-27-9
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C41H74N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h28-30,34-36,40,51-52H,4-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/t30-,34?,35+,36+,40-/m1/s1
InChI KeyJYLSVNBJLYCSSW-OPBWFHODSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.37ALOGPS
logP2.64ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity256.1 m³·mol⁻¹ChemAxon
Polarizability110.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004258
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023354
KNApSAcK IDNot Available
Chemspider ID17220830
KEGG Compound IDC02041
BioCyc IDICOSANOYL-COA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061151
PDB IDNot Available
ChEBI ID15527
References
Synthesis ReferenceLellouche, Jean-Paul; Levannier, Karine; Mioskowski, Charles. Process for synthesizing fatty acid-acylated thiol transporter derivatives, particularly of acyl coenzyme A derivatives, and the acyl coenzyme A derivatives thus obtained. Eur. Pat. Appl. (1994), 18 pp. CODEN: EPXXDW EP 618218 A1 19941005 CAN 123:170077 AN 1995:761488
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
GNPAT
Uniprot ID:
A4IF87
Molecular weight:
77664.0
Reactions
Eicosanoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LysoPA(20:0/0:0)details
Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme Adetails
General function:
Energy production and conversion
Specific function:
Catalyzes the oxidation of D-2-hydroxyglutarate to alpha-ketoglutarate.
Gene Name:
D2HGDH
Uniprot ID:
Q1JPD3
Molecular weight:
59056.0
Reactions
Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme Adetails
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) + Eicosanoyl-CoA → TG(14:0/14:0/20:0) + Coenzyme Adetails
DG(14:0/14:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:0/14:1(9Z)/20:0) + Coenzyme Adetails
DG(14:0/15:0/0:0) + Eicosanoyl-CoA → TG(14:0/15:0/20:0) + Coenzyme Adetails
DG(14:0/16:0/0:0) + Eicosanoyl-CoA → TG(14:0/16:0/20:0) + Coenzyme Adetails
DG(14:0/16:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:0/16:1(9Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:0/18:0/0:0) + Eicosanoyl-CoA → TG(14:0/18:0/20:0) + Coenzyme Adetails
DG(14:0/18:1(11Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:1(11Z)/20:0) + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:1(9Z)/20:0) + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:2(9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:0/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:3(6Z,9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:0/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:0/20:0/0:0) + Eicosanoyl-CoA → TG(14:0/20:0/20:0) + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/14:1(9Z)/20:0)[iso3] + Coenzyme Adetails
DG(14:1(9Z)/15:0/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/15:0/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/16:0/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/16:0/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/16:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/16:1(9Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:1(9Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(15:0/15:0/0:0) + Eicosanoyl-CoA → TG(15:0/15:0/20:0) + Coenzyme Adetails
DG(15:0/16:0/0:0) + Eicosanoyl-CoA → TG(15:0/16:0/20:0) + Coenzyme Adetails
DG(15:0/18:0/0:0) + Eicosanoyl-CoA → TG(15:0/18:0/20:0) + Coenzyme Adetails
DG(15:0/18:1(11Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:1(11Z)/20:0) + Coenzyme Adetails
DG(15:0/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:1(9Z)/20:0) + Coenzyme Adetails
DG(15:0/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(15:0/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:3(6Z,9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(15:0/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(15:0/20:0/0:0) + Eicosanoyl-CoA → TG(15:0/20:0/20:0) + Coenzyme Adetails
DG(16:0/16:0/0:0) + Eicosanoyl-CoA → TG(16:0/16:0/20:0)[iso3] + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Eicosanoyl-CoA → TG(16:0/16:1(9Z)/20:0) + Coenzyme Adetails
DG(16:0/18:0/0:0) + Eicosanoyl-CoA → TG(16:0/18:0/20:0)[iso6] + Coenzyme Adetails
DG(16:0/18:1(11Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:1(11Z)/20:0) + Coenzyme Adetails
DG(16:0/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:1(9Z)/20:0) + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(16:0/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:3(6Z,9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:0/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:0/20:0/0:0) + Eicosanoyl-CoA → TG(16:0/20:0/20:0)[iso3] + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/16:1(9Z)/20:0) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:0/20:0) + Coenzyme Adetails
DG(16:1(9Z)/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:1(9Z)/20:0) + Coenzyme Adetails
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:1(9Z)/20:0/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/20:0/20:0) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Eicosanoyl-CoA → TG(18:0/18:0/20:0)[iso3] + Coenzyme Adetails
DG(18:0/18:1(11Z)/0:0) + Eicosanoyl-CoA → TG(18:0/18:1(11Z)/20:0) + Coenzyme Adetails
DG(18:0/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(18:0/18:1(9Z)/20:0) + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:0/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:0/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:0/18:3(9Z,12Z,15Z)/20:0) + Coenzyme Adetails
DG(18:0/20:0/0:0) + Eicosanoyl-CoA → TG(18:0/20:0/20:0)[iso3] + Coenzyme Adetails
DG(18:1(11Z)/18:1(11Z)/0:0) + Eicosanoyl-CoA → TG(18:1(11Z)/18:1(11Z)/20:0) + Coenzyme Adetails
DG(18:1(11Z)/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(18:1(11Z)/18:1(9Z)/20:0) + Coenzyme Adetails
DG(18:1(11Z)/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:1(11Z)/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:1(11Z)/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:1(11Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0) + Coenzyme Adetails
DG(18:1(11Z)/20:0/0:0) + Eicosanoyl-CoA → TG(18:1(11Z)/20:0/20:0) + Coenzyme Adetails
DG(18:1(9Z)/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(18:1(9Z)/18:1(9Z)/20:0) + Coenzyme Adetails
DG(18:1(9Z)/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:1(9Z)/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:1(9Z)/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0) + Coenzyme Adetails
DG(18:1(9Z)/20:0/0:0) + Eicosanoyl-CoA → TG(18:1(9Z)/20:0/20:0) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(18:2(9Z,12Z)/20:0/0:0) + Eicosanoyl-CoA → TG(18:2(9Z,12Z)/20:0/20:0) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)[iso3] + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/20:0/0:0) + Eicosanoyl-CoA → TG(18:3(6Z,9Z,12Z)/20:0/20:0) + Coenzyme Adetails
DG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0)[iso3] + Coenzyme Adetails
DG(18:3(9Z,12Z,15Z)/20:0/0:0) + Eicosanoyl-CoA → TG(18:3(9Z,12Z,15Z)/20:0/20:0) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Eicosanoyl-CoA → TG(20:0/20:0/20:0) + Coenzyme Adetails