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

• ChemBase ID: 3843
• Molecular Formular: C22H37N8O18P3
• Molecular Mass: 794.493263
• Monoisotopic Mass: 794.14386627
• 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)NCCC[N+](=O)[O-]
• Canonical SMILES: O=C(NCCC[N+](=O)[O-])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/C22H37N8O18P3/c1-22(2,17(33)20(34)25-6-4-13(31)24-5-3-7-30(35)36)9-45-51(42,43)48-50(40,41)44-8-12-16(47-49(37,38)39)15(32)21(46-12)29-11-28-14-18(23)26-10-27-19(14)29/h10-12,15-17,21,32-33H,3-9H2,1-2H3,(H,24,31)(H,25,34)(H,40,41)(H,42,43)(H2,23,26,27)(H2,37,38,39)/t12-,15+,16-,17-,21+/m0/s1
• InChIKey: PUGKTLRHGHIDCJ-MHLKFSCXSA-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-[(3-nitropropyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @nitromethyldethia coenzyme A
• Synonyms: Nitromethyldethia Coenzyme A

Database IDs

• PubChem SID: 46507227; 160967280
• PubChem CID: 46936927

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8136794
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -10.838228
• LogD (pH = 7.4): -12.534398
• Log P: -7.313209
• Molar Refractivity: 165.7493 cm^3
• Polarizability: 65.81262 Å^3
• Polar Surface Area: 392.38 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.71
• LOG S: -2.32
• Solubility (Water): 3.79e+00 g/l

DETAILS

DrugBank - DB04230

Drug information: experimental