{[(2R,3R,4S,5S)-2-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 1704
• Molecular Formular: C10H14N5O8P
• Molecular Mass: 363.220621
• Monoisotopic Mass: 363.05799906
• SMILES: Nc1nc2c(ncn2[C@@H]2O[C@@H](CO)[C@H](O)[C@H]2OP(=O)(O)O)c(=O)[nH]1
• Canonical SMILES: OC[C@@H]1O[C@H]([C@@H]([C@H]1O)OP(=O)(O)O)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(23-24(19,20)21)5(17)3(1-16)22-9/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6+,9+/m0/s1
• InChIKey: WTIFIAZWCCBCGE-BZKDHIKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4S,5S)-2-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @guanosine-2'-monophosphate
• Synonyms: Guanosine-2'-Monophosphate

Database IDs

• PubChem SID: 160965161; 46506277
• PubChem CID: 46936264

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.6309953
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -5.378109
• LogD (pH = 7.4): -6.8182206
• Log P: -2.721966
• Molar Refractivity: 75.494 cm^3
• Polarizability: 28.927118 Å^3
• Polar Surface Area: 201.75 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.95
• LOG S: -2.01
• Solubility (Water): 3.56e+00 g/l

DETAILS

DrugBank - DB01937

Drug information: experimental