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

• ChemBase ID: 1663
• Molecular Formular: C14H19N6O10P
• Molecular Mass: 462.308621
• Monoisotopic Mass: 462.09002747
• SMILES: N[C@@H](CC(=O)O)C(=O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: OC(=O)C[C@@H](C(=O)O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)O)N
• InChI: InChI=1S/C14H19N6O10P/c15-5(1-7(21)22)14(25)30-31(26,27)28-2-6-9(23)10(24)13(29-6)20-4-19-8-11(16)17-3-18-12(8)20/h3-6,9-10,13,23-24H,1-2,15H2,(H,21,22)(H,26,27)(H2,16,17,18)/t5-,6-,9-,10+,13+/m0/s1
• InChIKey: QPBSGQWTJLPZNF-OQIRQZMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-4-[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-4-oxobutanoic acid
• IUPAC Traditional name: (3S)-3-amino-4-({[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-4-oxobutanoic acid
• Synonyms: Aspartyl-Adenosine-5'-Monophosphate

Database IDs

• PubChem SID: 46508800; 160965120
• PubChem CID: 46936251

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.7570244
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -6.4727836
• LogD (pH = 7.4): -7.829897
• Log P: -6.078701
• Molar Refractivity: 97.109 cm^3
• Polarizability: 38.96439 Å^3
• Polar Surface Area: 255.46 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.26
• LOG S: -2.25
• Solubility (Water): 2.59e+00 g/l

DETAILS

DrugBank - DB01895

Drug information: experimental