{[(2R,3S,5R)-3-hydroxy-5-{2-[(naphthalen-1-ylmethyl)amino]-6-oxo-6,9-dihydro-1H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 5862
• Molecular Formular: C21H22N5O7P
• Molecular Mass: 487.402441
• Monoisotopic Mass: 487.1256847
• SMILES: P(=O)(O)(O)OC[C@H]1O[C@@H](n2c3nc(NCc4c5ccccc5ccc4)[nH]c(=O)c3nc2)C[C@@H]1O
• Canonical SMILES: O[C@H]1C[C@@H](O[C@@H]1COP(=O)(O)O)n1cnc2c1nc(NCc1cccc3c1cccc3)[nH]c2=O
• InChI: InChI=1S/C21H22N5O7P/c27-15-8-17(33-16(15)10-32-34(29,30)31)26-11-23-18-19(26)24-21(25-20(18)28)22-9-13-6-3-5-12-4-1-2-7-14(12)13/h1-7,11,15-17,27H,8-10H2,(H2,29,30,31)(H2,22,24,25,28)/t15-,16+,17+/m0/s1
• InChIKey: COMPKRGNHXOXMN-GVDBMIGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R)-3-hydroxy-5-{2-[(naphthalen-1-ylmethyl)amino]-6-oxo-6,9-dihydro-1H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,5R)-3-hydroxy-5-{2-[(naphthalen-1-ylmethyl)amino]-6-oxo-1H-purin-9-yl}oxolan-2-yl]methoxyphosphonic acid
• Synonyms: 2'-deoxy-N-(naphthalen-1-ylmethyl)guanosine 5'-(dihydrogen phosphate)

Database IDs

• PubChem SID: 99444708; 160969289
• PubChem CID: 46937134

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.1218352
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.3349173
• LogD (pH = 7.4): -2.4619684
• Log P: 0.98108786
• Molar Refractivity: 119.8207 cm^3
• Polarizability: 46.6808 Å^3
• Polar Surface Area: 167.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.31
• LOG S: -3.01
• Solubility (Water): 4.78e-01 g/l

DETAILS

DrugBank - DB08237

Drug information: experimental