{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{6-[(3-methylbutyl)amino]-2-(methylsulfanyl)-9H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 5812
• Molecular Formular: C16H26N5O7PS
• Molecular Mass: 463.445701
• Monoisotopic Mass: 463.12905583
• SMILES: OP(=O)(O)OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c(NCCC(C)C)nc(nc12)SC
• Canonical SMILES: CSc1nc(NCCC(C)C)c2c(n1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(O)O
• InChI: InChI=1S/C16H26N5O7PS/c1-8(2)4-5-17-13-10-14(20-16(19-13)30-3)21(7-18-10)15-12(23)11(22)9(28-15)6-27-29(24,25)26/h7-9,11-12,15,22-23H,4-6H2,1-3H3,(H,17,19,20)(H2,24,25,26)/t9-,11-,12-,15-/m1/s1
• InChIKey: LCHGAOHLDYRACA-SDBHATRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-3,4-dihydroxy-5-{6-[(3-methylbutyl)amino]-2-(methylsulfanyl)-9H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,4R,5R)-3,4-dihydroxy-5-{6-[(3-methylbutyl)amino]-2-(methylsulfanyl)purin-9-yl}oxolan-2-yl]methoxyphosphonic acid
• Synonyms: 2-METHYLTHIO-N6-ISOPENTENYL-ADENOSINE-5'-MONOPHOSPHATE

Database IDs

• PubChem SID: 99444656; 160969239
• PubChem CID: 46937130

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.1998928
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.3952777
• LogD (pH = 7.4): -2.5247521
• Log P: -1.1861157
• Molar Refractivity: 110.689 cm^3
• Polarizability: 43.011383 Å^3
• Polar Surface Area: 172.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.64
• LOG S: -2.43
• Solubility (Water): 1.71e+00 g/l

DETAILS

DrugBank - DB08185

Drug information: experimental