1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ5-pyridin-1-ylium

• ChemBase ID: 128597
• Molecular Formular: C21H28N7O17P3
• Molecular Mass: 743.405003
• Monoisotopic Mass: 743.07545236
• SMILES: O=C(N)c1ccc[n+](c1)[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)COP(=O)([O-])OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(ncnc23)N)[C@H](OP(=O)(O)O)[C@@H]1O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1[n+]1cccc(c1)C(=O)N)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)(O)O)n1cnc2c1ncnc2N)O)[O-]
• InChI: InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
• InChIKey: XJLXINKUBYWONI-NNYOXOHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: nadp zwitterion
• Synonyms: Nicotinamide adenine dinucleotide phosphate

Database IDs

• CAS Number: 53-59-8
• PubChem SID: 162222904
• PubChem CID: 5885
• CHEBI ID: 44409
• CHEMBL: 213053
• Chemspider ID: 5674
• MeSH Name: NADP
• Wikipedia Title: Nicotinamide_adenine_dinucleotide_phosphate

CALCULATED PROPERTIES

• Acid pKa: 0.6620108
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -13.820282
• LogD (pH = 7.4): -15.519069
• Log P: -10.449491
• Molar Refractivity: 151.7481 cm^3
• Polarizability: 60.78195 Å^3
• Polar Surface Area: 367.62 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false