{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3,3,3-trifluoro-2-oxopropyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 1736
• Molecular Formular: C24H37F3N7O17P3S
• Molecular Mass: 877.5687726
• Monoisotopic Mass: 877.11315831
• SMILES: CC(C)(CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1OP(=O)(O)O)n1cnc2c1ncnc2N)[C@@H](O)C(=O)NCCC(=O)NCCSCC(=O)C(F)(F)F
• Canonical SMILES: O=C(NCCSCC(=O)C(F)(F)F)CCNC(=O)[C@@H](C(CO[P@](=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
• InChI: InChI=1S/C24H37F3N7O17P3S/c1-23(2,18(38)21(39)30-4-3-14(36)29-5-6-55-8-13(35)24(25,26)27)9-48-54(45,46)51-53(43,44)47-7-12-17(50-52(40,41)42)16(37)22(49-12)34-11-33-15-19(28)31-10-32-20(15)34/h10-12,16-18,22,37-38H,3-9H2,1-2H3,(H,29,36)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/t12-,16+,17-,18-,22+/m0/s1
• InChIKey: XDIQTPZOIIYCTR-DBXDFDKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3,3,3-trifluoro-2-oxopropyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @trifluoroacetonyl coenzyme A
• Synonyms: Trifluoroacetonyl Coenzyme A

Database IDs

• PubChem SID: 160965192; 46506152
• PubChem CID: 46936270

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8136794
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -9.324518
• LogD (pH = 7.4): -10.968539
• Log P: -5.8002057
• Molar Refractivity: 178.1847 cm^3
• Polarizability: 70.2072 Å^3
• Polar Surface Area: 363.63 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.21
• LOG S: -2.32
• Solubility (Water): 4.21e+00 g/l

DETAILS

DrugBank - DB01969

Drug information: experimental