disodium 1-[(3R,4S,5R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(hydrogen phosphonatooxy)-3-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ5-pyridin-1-ylium

• ChemBase ID: 155922
• Molecular Formular: C21H26N7Na2O17P3
• Molecular Mass: 787.368663
• Monoisotopic Mass: 787.03934086
• SMILES: c1cc(c[n+](c1)C1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)OP(=O)(O)[O-])O)O)O)C(=O)N.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](OC1[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-].[Na+].[Na+]
• InChI: InChI=1S/C21H28N7O17P3.2Na/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);;/q;2*+1/p-2/t10-,11-,13-,14-,15-,16-,20?,21-;;/m1../s1
• InChIKey: WSDDJLMGYRLUKR-FHQWUTKFSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 1-[(3R,4S,5R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(hydrogen phosphonatooxy)-3-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: disodium 1-[(3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-(hydrogen phosphonatooxy)-3-hydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• Synonyms: β-NADP-Na2; β-NADH phosphate disodium salt; Triphosphopyridine nucleotide disodium salt; β-Nicotinamide adenine dinucleotide phosphate disodium salt; β-NADH phosphate 二钠盐; Triphosphopyridine nucleotide 二钠盐; β-Nicotinamide adenine dinucleotide phosphate 二钠盐

Database IDs

• CAS Number: 24292-60-2
• EC Number: 246-129-8
• MDL Number: MFCD00065390
• PubChem SID: 162250060; 24889813
• PubChem CID: 16218773

CALCULATED PROPERTIES

• Acid pKa: 0.6552737
• H Acceptors: 17
• H Donor: 6
• LogD (pH = 5.5): -13.820264
• LogD (pH = 7.4): -15.519069
• Log P: -10.446861
• Molar Refractivity: 149.5047 cm^3
• Polarizability: 60.544743 Å^3
• Polar Surface Area: 373.28 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (calc. based on dry substance, enzymatic)
• Impurities: ≤7% water
• Cation Traces: Ca: ≤1000 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤10 mg/kg; K: ≤1000 mg/kg; Mg: ≤100 mg/kg; Mn: ≤5 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤50 mg/kg
• Empirical Formula (Hill Notation): C21H26N7Na2O17P3

DETAILS

Sigma Aldrich - 93205

Application
Nicotinamide adenine dinucleotide phosphate (NADP) and NADPH form a redox pair. NADP/NADPH is a coenzyme that supports redox reactions via the transport of electrons in a vast array of applications, especially anaerobic reactions such as lipid and nucleic acid synthesis. NADP/NADPH is a coenzyme couple in various cytochrome P450 systems and oxidase/reductase reaction systems, such as the thioredoxin reductase/thioredoxin system.