{[2-(6-amino-9H-purin-9-yl)-5-[({[({[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 sodium

• ChemBase ID: 155110
• Molecular Formular: C21H30N7NaO17P3
• Molecular Mass: 768.410653
• Monoisotopic Mass: 768.08087171
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N1C=CCC(=C1)C(=O)N)O)O)O)OP(=O)(O)O)N.[Na]
• Canonical SMILES: OC1C(O)C(OC1N1C=CCC(=C1)C(=O)N)COP(=O)(OP(=O)(OCC1OC(C(C1O)OP(=O)(O)O)n1cnc2c1ncnc2N)O)O.[Na]
• InChI: InChI=1S/C21H30N7O17P3.Na/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;/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)
• InChIKey: WVIHKRDKCOXNAG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[2-(6-amino-9H-purin-9-yl)-5-[({[({[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 sodium
• IUPAC Traditional name: [2-(6-aminopurin-9-yl)-5-{[({[5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid sodium
• Synonyms: 3′-NADPH; 3′-TPNH; β-Nicotinamide adenine dinucleotide 3′-phosphate reduced form sodium salt

Database IDs

• EC Number: 220-163-3
• MDL Number: MFCD00135611
• PubChem SID: 162249248; 24897769
• PubChem CID: 16219766

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
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%
• Empirical Formula (Hill Notation): C21H30N7O17P3

DETAILS

Sigma Aldrich - N6132

Caution
This is not the common β-NADPH required in the usual enzyme systems.
Other Notes
Analog of β-NADPH, chemically reduced
Application
β-Nicotinamide adenine dinucleotide 3′-phosphate reduced (3′-NADPH) may be used as an inhibitory analogue to study the specificity and kinetics of NADP+/NADPH-dependent enzymes. 3′-NADPH is used to study copper ion aggregation of prion protein.