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

• ChemBase ID: 1739
• Molecular Formular: C10H14N5O8P
• Molecular Mass: 363.220621
• Monoisotopic Mass: 363.05799906
• SMILES: Nc1nc2c(ncn2[C@@H]2O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]2O)c(=O)[nH]1
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1cnc2c1nc(N)[nH]c2=O)COP(=O)(O)O
• InChI: InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6+,9+/m0/s1
• InChIKey: RQFCJASXJCIDSX-BZKDHIKHSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 85-32-5
• PubChem SID: 46504973; 160965195
• PubChem CID: 5748251

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0546672
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -5.2467523
• LogD (pH = 7.4): -6.360609
• Log P: -2.9361746
• Molar Refractivity: 75.494 cm^3
• Polarizability: 28.927122 Å^3
• Polar Surface Area: 201.75 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.99
• LOG S: -2.01
• Solubility (Water): 3.56e+00 g/l

DETAILS

DrugBank - DB01972

• Drug Groups: experimental
• Description: Guanosine 5'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. [PubChem]