(R)-{[(S)-{[(S)-{[(S)-([(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato)]oxy}phosphinato]oxy}phosphinato]oxy}({[(S)-([(2S,3S,5S)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl phosphonato)]oxy})phosphinate

• ChemBase ID: 3486
• Molecular Formular: C20H24N10O22P5-----
• Molecular Mass: 911.327165
• Monoisotopic Mass: 910.97547061
• SMILES: Cc1cn([C@@H]2C[C@H](N=[N+]=[N-])[C@@H](COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OC[C@@H]3O[C@H]([C@H](O)[C@H]3O)n3cnc4c3ncnc4N)O2)c(=O)[nH]c1=O
• Canonical SMILES: [N-]=[N+]=N[C@H]1C[C@H](O[C@@H]1COP(=O)(OP(=O)(OP(=O)(OP(=O)(OP(=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)[O-])[O-])[O-])[O-])[O-])n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C20H29N10O22P5/c1-8-3-29(20(34)26-18(8)33)12-2-9(27-28-22)10(47-12)4-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-5-11-14(31)15(32)19(48-11)30-7-25-13-16(21)23-6-24-17(13)30/h3,6-7,9-12,14-15,19,31-32H,2,4-5H2,1H3,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,24)(H,26,33,34)/p-5/t9-,10+,11-,12-,14-,15+,19+/m0/s1
• InChIKey: QNIWSXQXLJIUJW-HCYMPCJFSA-I

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-{[(S)-{[(S)-{[(S)-([(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato)]oxy}phosphinato]oxy}phosphinato]oxy}({[(S)-([(2S,3S,5S)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl phosphonato)]oxy})phosphinate
• IUPAC Traditional name: (R)-[(S)-[(S)-[(S)-([(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato)]oxyphosphinato]oxyphosphinato]oxy[(S)-([(2S,3S,5S)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl phosphonato)]oxyphosphinate
• Synonyms: P1-(5'-Adenosyl)P5-(5'-(3'azido-3'-Deoxythymidyl))Pentaphosphate

Database IDs

• PubChem SID: 46505090; 160966925
• PubChem CID: 46936803

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.38760135
• H Acceptors: 22
• H Donor: 4
• LogD (pH = 5.5): -14.772342
• LogD (pH = 7.4): -15.291878
• Log P: -6.076114
• Molar Refractivity: 169.8771 cm^3
• Polarizability: 70.065765 Å^3
• Polar Surface Area: 463.41 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.37
• LOG S: -1.4
• Solubility (Water): 3.98e+01 g/l

DETAILS

DrugBank - DB03845

Drug information: experimental