Showing Metabocard for (2E)-hexadecenoyl-CoA (BASm0004131)

Common Name(2e)-hexadecenoyl-coa
Description(2E)-Hexadecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme enoyl-CoA hydratase [EC:4.2.1.17]. It is also the substrate of the enzyme trans-2-enoyl-CoA reductase [EC:1.3.1.38], in fatty acid elongation. (PMID: 1278159 , KEGG)
Structure
Molecular FormulaC37H60N7O17P3S
Average Mass999.89500
Monoisotopic Mass999.29792
IUPAC Name[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl {[(3R)-3-{[2-({2-[(2E)-hexadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl phosphonato]oxy}phosphonate
Traditional Name[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl [(3r)-3-{[2-({2-[(2e)-hexadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl phosphonato]oxyphosphonate
CAS Registry Number4460-95-1
SMILESCCCCCCCCCCCCC/C=C/C(=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/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h16-17,24-26,30-32,36,47-48H,4-15,18-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/p-4/b17-16+/t26-,30-,31-,32+,36-/m1/s1
InChI KeyJUPAQFRKPHPXLD-MSHHSVQMSA-J
CHEBI IDCHEBI:61526
HMDB IDHMDB0003945
MiMeDB IDMMDBc0029746
Pathways
NameSMPDB/PathBank
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Ethylmalonic Encephalopathy
Glutaric Aciduria Type I
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids
Carnitine palmitoyl transferase deficiency (I)
Long chain acyl-CoA dehydrogenase deficiency (LCAD)
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)
Carnitine palmitoyl transferase deficiency (II)
Medium chain acyl-coa dehydrogenase deficiency (MCAD)
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)
Trifunctional protein deficiency
StateSolid
Water Solubility1.22e+00 g/l
logP3.34
logS-2.94
pKa (Strongest Acidic)0.83
pKa (Strongest Basic)4.95
Hydrogen Acceptor Count17
Hydrogen Donor Count5
Polar Surface Area374.95 Ų
Rotatable Bond Count33
Physiological Charge-4
Formal Charge-4
Refractivity233.25 m³·mol⁻¹
Polarizability98.77

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