[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 1612
• Molecular Formular: C10H16N5O13P3
• Molecular Mass: 507.181023
• Monoisotopic Mass: 506.99574549
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO[P@@](=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](OP(=O)(O)O)[C@@H](O[C@H]1n1cnc2c1ncnc2N)CO[P@](=O)(OP(=O)(O)O)O
• InChI: InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-31(23,24)28-30(20,21)22/h2-4,6-7,10,16H,1H2,(H,23,24)(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6+,7-,10+/m0/s1
• InChIKey: GBBWIZKLHXYJOA-PERBPWGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: {[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: 3'-Phosphate-Adenosine-5'-Diphosphate

Database IDs

• PubChem SID: 46509162; 160965069
• PubChem CID: 46936234

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8041604
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -9.750108
• LogD (pH = 7.4): -11.646054
• Log P: -6.2340255
• Molar Refractivity: 95.8143 cm^3
• Polarizability: 38.49302 Å^3
• Polar Surface Area: 279.13 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.08
• LOG S: -2.04
• Solubility (Water): 4.61e+00 g/l

DETAILS

DrugBank - DB01842

Drug information: experimental