5-[2-({[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)ethyl]-4-methyl-1,3-thiazole-2-carboxylic acid

• ChemBase ID: 3955
• Molecular Formular: C17H22N6O12P2S
• Molecular Mass: 596.402102
• Monoisotopic Mass: 596.04916443
• SMILES: Cc1c(CCO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](O)[C@H]2O)n2cnc3c2ncnc3N)sc(n1)C(=O)O
• Canonical SMILES: O[C@H]1[C@H](CO[P@](=O)(O[P@@](=O)(OCCc2sc(nc2C)C(=O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C17H22N6O12P2S/c1-7-9(38-15(22-7)17(26)27)2-3-32-36(28,29)35-37(30,31)33-4-8-11(24)12(25)16(34-8)23-6-21-10-13(18)19-5-20-14(10)23/h5-6,8,11-12,16,24-25H,2-4H2,1H3,(H,26,27)(H,28,29)(H,30,31)(H2,18,19,20)/t8-,11-,12+,16+/m0/s1
• InChIKey: VGXBGQACJQRWLV-LQZWOCCTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-({[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)ethyl]-4-methyl-1,3-thiazole-2-carboxylic acid
• IUPAC Traditional name: 5-{2-[({[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]ethyl}-4-methyl-1,3-thiazole-2-carboxylic acid
• Synonyms: Adenosine Diphosphate 5-(Beta-Ethyl)-4-Methyl-Thiazole-2-Carboxylic Acid

Database IDs

• PubChem SID: 160967390; 46507777
• PubChem CID: 46936956; 6323213

CALCULATED PROPERTIES

JChem

• Acid pKa: -7.028098
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -7.6867886
• LogD (pH = 7.4): -9.382209
• Log P: -4.124674
• Molar Refractivity: 125.2191 cm^3
• Polarizability: 49.32852 Å^3
• Polar Surface Area: 271.79 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.5
• LOG S: -2.79
• Solubility (Water): 1.05e+00 g/l

DETAILS

DrugBank - DB04362

Drug information: experimental