Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:45:11 UTC
Update Date2022-12-15 22:52:17 UTC
Metabolite IDMMDBc0047837
Metabolite Identification
Common NameDocosanoyl-CoA
DescriptionDocosanoyl-CoA belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Docosanoyl-CoA is a strong basic compound (based on its pKa). Within humans, docosanoyl-CoA participates in a number of enzymatic reactions. In particular, docosanoyl-CoA and glycerol 3-phosphate can be converted into lpa(22:0/0:0); which is catalyzed by the enzyme glycerol-3-phosphate acyltransferase. In addition, lpa(22:0/0:0) and docosanoyl-CoA can be converted into PA(22:0/22:0); which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In humans, docosanoyl-CoA is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. has a free energy change near zero. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. Docosanoyl-CoA is a acyl-CoA with the C-22 fatty acid Acyl chain moiety.
Structure
Synonyms
ValueSource
Behenoyl-CoAHMDB
Behenoyl-coenzyme AHMDB
Molecular FormulaC43H74N7O17P3S
Average Mass1086.071
Monoisotopic Mass1085.407474203
IUPAC Name3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
Traditional Name3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C43H78N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/p-4/t32-,36+,37+,38?,42-/m1/s1
InChI KeyNDDZLVOCGALPLR-JEAMVCTESA-J