Showing metabocard for Arachidonyl-CoA (BMDB0006523)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:22:57 UTC
Update Date2020-04-22 15:17:43 UTC
BMDB IDBMDB0006523
Secondary Accession Numbers
  • BMDB06523
Metabolite Identification
Common NameArachidonyl-CoA
DescriptionArachidonyl-CoA is a very strong basic compound (based on its pKa). Within cattle, arachidonyl-CoA participates in a number of enzymatic reactions. In particular, arachidonyl-CoA and glycerol 3-phosphate can be converted into lpa(20:4(5Z,8Z,11Z,14Z)/0:0); which is mediated by the enzyme glycerol-3-phosphate acyltransferase. In addition, lpa(20:4(5Z,8Z,11Z,14Z)/0:0) and arachidonyl-CoA can be converted into PA(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) through its interaction with the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In cattle, arachidonyl-CoA is involved in the metabolic pathway called de novo triacylglycerol biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-4-({[({[(2R,4R,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-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidateGenerator
(2R)-4-({[({[(2R,4R,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-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidateGenerator
(2R)-4-({[({[(2R,4R,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-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acidGenerator
Chemical FormulaC41H66N7O17P3S
Average Molecular Weight1053.99
Monoisotopic Molecular Weight1053.344875861
IUPAC Name(2R)-4-({[({[(2R,4R,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-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid
Traditional Name(2R)-4-[({[(2R,4R,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-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC(=O)SCCN=C(O)CCN=C(O)[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)C1([H])OP(O)(O)=O
InChI Identifier
InChI=1S/C41H66N7O17P3S/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/h8-9,11-12,14-15,17-18,28-30,34-36,40,51-52H,4-7,10,13,16,19-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-,15-14-,18-17-/t30-,34-,35?,36+,40-/m1/s1
InChI KeyJDEPVTUUCBFJIW-MTUFRFTBSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.64ALOGPS
logP1.19ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)6.42ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity260.56 m³·mol⁻¹ChemAxon
Polarizability103.66 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4905410200-fb1158e48c4fd3d15f9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1916320000-b4b2f620774a7db7a50fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1902200000-9f969470361c9f1d0b0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9741331500-174cc65f7d543dcecdc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910210100-c2c194f27db32bfebdadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-2a95342113b08ca1f88bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceLucet-Levannier, Karine; Lellouche, Jean-Paul; Mioskowski, Charles. Polysilylated coenzyme A for a high-yielding preparation of very lipophilic acyl coenzymes A in anhydrous organic solvents. Journal of the American Chemical Society (1995), 117(28), 7546-
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available