Showing Metabocard for (9Z,12Z)-octadecadienoyl-CoA (BASm0002644)

Common Name(9z,12z)-octadecadienoyl-coa
DescriptionLinoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long-chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid beta-oxidation. ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates (PMID: 17184976 , 16020546 ).
Structure
Molecular FormulaC39H62N7O17P3S
Average Mass1025.94000
Monoisotopic Mass1025.31577
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9E,12E)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9e,12e)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number6709-57-5
SMILESCCCCC/C=C\C/C=C\CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]
InChI IdentifierInChI=1S/C39H66N7O17P3S/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/h8-9,11-12,26-28,32-34,38,49-50H,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)/p-4/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1
InChI KeyYECLLIMZHNYFCK-RRNJGNTNSA-J
CHEBI IDCHEBI:57383
HMDB IDHMDB0001064
MiMeDB IDMMDBc0048666
Pathways
NameSMPDB/PathBank
Plasmalogen Synthesis
StateExpected Solid
Water Solubility8.57e-01 g/l
logP2.83
logS-3.08
pKa (Strongest Acidic)0.83
pKa (Strongest Basic)4.95
Hydrogen Acceptor Count17
Hydrogen Donor Count9
Polar Surface Area363.63 Ų
Rotatable Bond Count34
Physiological Charge-4
Formal Charge0
Refractivity248.08 m³·mol⁻¹
Polarizability101.78

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT