{[(2S,3R,4R,5R)-5-(6-amino-7H-purin-7-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 3524
• Molecular Formular: C10H14N5O7P
• Molecular Mass: 347.221221
• Monoisotopic Mass: 347.06308444
• SMILES: Nc1ncnc2c1n(cn2)[C@@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1cnc2c1c(N)ncn2)COP(=O)(O)O
• InChI: InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)14-3-15(5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7+,10+/m0/s1
• InChIKey: NVOIXARBSSLBAS-FCIPNVEPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-7H-purin-7-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: @α-adenosine monophosphate
• Synonyms: Alpha-Adenosine Monophosphate

Database IDs

• PubChem SID: 160966963; 46505562
• PubChem CID: 46936820

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.8888171
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.8537
• LogD (pH = 7.4): -5.7900643
• Log P: -5.2720423
• Molar Refractivity: 75.6887 cm^3
• Polarizability: 29.092335 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.12
• LOG S: -2.02
• Solubility (Water): 3.34e+00 g/l

DETAILS

DrugBank - DB03887

Drug information: experimental