Showing Metabocard for choloyl-CoA (BASm0002635)

Common NameCholoyl-coa
DescriptionCholoyl-CoA is an intermediate metabolite in the Bile acid biosynthesis (KEGG). The conjugation of bile acids to glycine and taurine for excretion into bile occurs via a reaction catalyzed by the enzyme Bile acid-CoA:amino acid N-acyltransferase (BACAT) catalyzes.
Structure
Molecular FormulaC45H74N7O20P3S
Average Mass1158.09000
Monoisotopic Mass1157.39222
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({4-[(1S,5R,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-({4-[(1s,5r,9r,11s,16s)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbam
CAS Registry NumberNot Available
SMILESC[C@H](CCC(=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-])[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
InChI IdentifierInChI=1S/C45H74N7O20P3S/c1-23(26-7-8-27-34-28(18-31(55)45(26,27)5)44(4)12-10-25(53)16-24(44)17-29(34)54)6-9-33(57)76-15-14-47-32(56)11-13-48-41(60)38(59)43(2,3)20-69-75(66,67)72-74(64,65)68-19-30-37(71-73(61,62)63)36(58)42(70-30)52-22-51-35-39(46)49-21-50-40(35)52/h21-31,34,36-38,42,53-55,58-59H,6-20H2,1-5H3,(H,47,56)(H,48,60)(H,64,65)(H,66,67)(H2,46,49,50)(H2,61,62,63)/t23?,24?,25-,26?,27+,28+,29-,30-,31+,34?,36-,37-,38?,42-,44?,45?/m1/s1
InChI KeyZKWNOTQHFKYUNU-TVKZAFKCSA-N
CHEBI IDCHEBI:57373
HMDB IDHMDB0001374
Pathways
NameSMPDB/PathBank
Primary bile acid biosynthesis
Congenital Bile Acid Synthesis Defect Type II
Cerebrotendinous Xanthomatosis (CTX)
Zellweger Syndrome
Familial Hypercholanemia (FHCA)
Congenital Bile Acid Synthesis Defect Type III
27-Hydroxylase Deficiency
StateSolid
Water Solubility1.49e+00 g/l
logP0.56
logS-2.89
pKa (Strongest Acidic)0.83
pKa (Strongest Basic)4.95
Hydrogen Acceptor Count20
Hydrogen Donor Count12
Polar Surface Area424.32 Ų
Rotatable Bond Count24
Physiological Charge-4
Formal Charge0
Refractivity270.35 m³·mol⁻¹
Polarizability114.43

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