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

• ChemBase ID: 1824
• Molecular Formular: C15H23N5O14P2
• Molecular Mass: 559.315742
• Monoisotopic Mass: 559.0716737
• SMILES: Nc1c2ncn([C@@H]3O[C@H](CO[P@](=O)(O)O[P@](=O)(O)OC[C@H]4O[C@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H]3O)c2ncn1
• Canonical SMILES: O[C@@H]1[C@@H](CO[P@@](=O)(O[P@@](=O)(OC[C@H]2O[C@@H]([C@@H]([C@@H]2O)O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)/t5-,6-,8-,9-,10-,11-,14-,15+/m1/s1
• InChIKey: SRNWOUGRCWSEMX-ZQSHOCFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid
• IUPAC Traditional name: adenosine-5-diphosphoribose
• Synonyms: ADPR; Adenosine-5-Diphosphoribose

Database IDs

• PubChem SID: 46508870; 160965279
• PubChem CID: 447048

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7855422
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -8.472119
• LogD (pH = 7.4): -8.788511
• Log P: -6.6829395
• Molar Refractivity: 111.1233 cm^3
• Polarizability: 45.306454 Å^3
• Polar Surface Area: 291.52 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.8
• LOG S: -2.19
• Solubility (Water): 3.61e+00 g/l

DETAILS

DrugBank - DB02059

Drug information: experimental