1-[(2R,3R,4R,5S)-5-({[(S)-({[(2S,3S,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-1$l^{5}-pyridin-1-ylium

• ChemBase ID: 3138
• Molecular Formular: C21H28N7O17P3
• Molecular Mass: 743.405003
• Monoisotopic Mass: 743.07545236
• SMILES: NC(=O)c1ccc[n+](c1)[C@@H]1O[C@@H](COP(=O)([O-])O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](OP(=O)(O)O)[C@H]2O)n2cnc3c2ncnc3N)[C@H](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)(O[P@@](=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+/m0/s1
• InChIKey: XJLXINKUBYWONI-XCSFTKGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4R,5S)-5-({[(S)-({[(2S,3S,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-1$l^{5}-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3R,4R,5S)-5-({[(S)-([(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato)]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1$l^{5}-pyridin-1-ylium
• Synonyms: 2'-Monophosphoadenosine 5'-Diphosphoribose

Database IDs

• PubChem SID: 160966582; 46507953
• PubChem CID: 46936685

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.65010595
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -13.794226
• LogD (pH = 7.4): -15.51892
• Log P: -11.463356
• 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

ALOGPS 2.1

• Log P: -0.81
• LOG S: -2.22
• Solubility (Water): 4.84e+00 g/l

DETAILS

DrugBank - DB03461

• Drug Groups: experimental
• Description: Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed)