sodium 1-[(3R,4S,5R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-phosphonooxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ5-pyridin-1-ylium hydrate

• ChemBase ID: 153693
• Molecular Formular: C21H29N7NaO17P3
• Molecular Mass: 767.402713
• Monoisotopic Mass: 767.07304667
• 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)P(=O)(O)O)O)O)O)C(=O)N.O.[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)P(=O)(O)O)n1cnc2c1ncnc2N)[O-])[O-].O.[Na+]
• InChI: InChI=1S/C21H28N7O16P3.Na.H2O/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(45(33,34)35)14(30)11(43-21)6-41-47(38,39)44-46(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);;1H2/q;+1;/p-1/t10-,11-,13-,14-,15-,16-,20?,21-;;/m1../s1
• InChIKey: NLIGHACCLYZCOM-FHQWUTKFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 1-[(3R,4S,5R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-phosphonooxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium hydrate
• IUPAC Traditional name: sodium 1-[(3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium hydrate
• Synonyms: β-NADP-Na; β-NADP-sodium salt; Coenzyme II sodium salt; NADP; TPN-Na; TPN; Triphosphopyridine nucleotide sodium salt; β-Nicotinamide adenine dinucleotide phosphate sodium salt; 三磷酸吡啶核苷酸 钠盐; β-烟酰胺腺嘌呤二核苷酸磷酸 钠盐

Database IDs

• CAS Number: 1184-16-3
• EC Number: 214-664-6
• MDL Number: MFCD00036973
• Beilstein Number: 4779954
• PubChem SID: 24897856; 162247832; 24897850
• PubChem CID: 16219781

CALCULATED PROPERTIES

• Acid pKa: 1.4304235
• H Acceptors: 17
• H Donor: 7
• LogD (pH = 5.5): -13.994524
• LogD (pH = 7.4): -14.317947
• Log P: -11.373889
• Molar Refractivity: 148.9178 cm^3
• Polarizability: 59.87789 Å^3
• Polar Surface Area: 361.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 175-178 °C (dec.)(lit.)

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

• Packaging: pkg of 10 mg (per vial); pkg of 5 mg (per vial)
• Linear Formula: C21H27N7O17P3 · Na

DETAILS

Sigma Aldrich - N8035

Biochem/physiol Actions
Electron acceptor
Other Notes
Packaged based on NADP content as determined by UV-Vis.
This is the common form of NADP. Do not confuse with 3′-NADP or α-NADP.
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).

Sigma Aldrich - N8160

Biochem/physiol Actions
Electron acceptor
Other Notes
Packaged based on NADP content as determined by UV-Vis.
This is the common form of NADP. Do not confuse with 3′-NADP or α-NADP.
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).