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

• ChemBase ID: 1582
• Molecular Formular: C10H15N5O10P2
• Molecular Mass: 427.201122
• Monoisotopic Mass: 427.02941497
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](COP(=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)COP(=O)(O)O
• InChI: InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6+,7-,10+/m0/s1
• InChIKey: WHTCPDAXWFLDIH-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}phosphonic acid
• IUPAC Traditional name: @adenosine-3'-5'-diphosphate
• Synonyms: Adenosine-3'-5'-Diphosphate

Database IDs

• PubChem SID: 46507388; 160965039
• PubChem CID: 46936223

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.7003793
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -7.354658
• LogD (pH = 7.4): -9.707862
• Log P: -6.1310134
• Molar Refractivity: 84.9414 cm^3
• Polarizability: 33.697124 Å^3
• Polar Surface Area: 232.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.63
• LOG S: -2.11
• Solubility (Water): 3.33e+00 g/l

DETAILS

DrugBank - DB01812

Drug information: experimental