(R)-([(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R)-2-azaniumyl-3-(1H-imidazol-4-yl)propanoyl]oxy}phosphonate)

• ChemBase ID: 3814
• Molecular Formular: C16H21N8O8P
• Molecular Mass: 484.360501
• Monoisotopic Mass: 484.1219963
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](COP(=O)([O-])OC(=O)[C@H]([NH3+])Cc2c[nH]cn2)[C@H](O)[C@H]1O
• Canonical SMILES: O=C([C@@H](Cc1c[nH]cn1)[NH3+])OP(=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)[O-]
• InChI: InChI=1S/C16H21N8O8P/c17-8(1-7-2-19-4-20-7)16(27)32-33(28,29)30-3-9-11(25)12(26)15(31-9)24-6-23-10-13(18)21-5-22-14(10)24/h2,4-6,8-9,11-12,15,25-26H,1,3,17H2,(H,19,20)(H,28,29)(H2,18,21,22)/t8-,9+,11+,12-,15-/m1/s1
• InChIKey: XTFBSLZFYLGYAT-AWUSFDAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-([(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R)-2-azaniumyl-3-(1H-imidazol-4-yl)propanoyl]oxy}phosphonate)
• IUPAC Traditional name: (R)-([(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2R)-2-aminio-3-(1H-imidazol-4-yl)propanoyl]oxyphosphonate)
• Synonyms: Histidyl-Adenosine Monophosphate

Database IDs

• PubChem SID: 46508578; 160967251
• PubChem CID: 46936920

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.7589826
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -4.776982
• LogD (pH = 7.4): -4.5494084
• Log P: -4.357253
• Molar Refractivity: 118.2407 cm^3
• Polarizability: 42.674225 Å^3
• Polar Surface Area: 251.29 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.34
• LOG S: -2.53
• Solubility (Water): 1.57e+00 g/l

DETAILS

DrugBank - DB04201

Drug information: experimental