tetrakis(cyclohexanamine); {[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 155209
• Molecular Formular: C45H82N11O17P3
• Molecular Mass: 1142.117363
• Monoisotopic Mass: 1141.51030011
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=CCC(=C1)C(=O)N)O)O)O)OP(=O)(O)O)N.C1CCC(CC1)N.C1CCC(CC1)N.C1CCC(CC1)N.C1CCC(CC1)N
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1N1C=CCC(=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.NC1CCCCC1.NC1CCCCC1.NC1CCCCC1.NC1CCCCC1
• InChI: InChI=1S/C21H30N7O17P3.4C6H13N/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;4*7-6-4-2-1-3-5-6/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);4*6H,1-5,7H2/t10-,11-,13-,14-,15-,16-,20-,21-;;;;/m1..../s1
• InChIKey: PTKRUDMLGIIORX-ITGWJZMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrakis(cyclohexanamine); {[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: tetrakis(cyclohexylamine); nadph
• Synonyms: NADPH; TPNH; Triphosphopyridine nucleotide, reduced form; β-NADPH; β-Nicotinamide adenine dinucleotide phosphate, reduced tetra(cyclohexylammonium) salt

Database IDs

• CAS Number: 100929-71-3
• MDL Number: MFCD00079504
• PubChem SID: 162249347
• PubChem CID: 71312102

CALCULATED PROPERTIES

• Acid pKa: 0.65526855
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -10.989814
• LogD (pH = 7.4): -12.689332
• Log P: -6.418074
• Molar Refractivity: 153.8726 cm^3
• Polarizability: 61.29122 Å^3
• Polar Surface Area: 364.15 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: ≥95%
• Cation Traces: Na: ≤0.1%
• Empirical Formula (Hill Notation): C21H30N7O17P3 · 4C6H13N

DETAILS

Sigma Aldrich - N5130

Biochem/physiol Actions
Electron donor; cofactor for nitric oxide synthetase
Preparation Note
Chemically reduced.
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).