{[5-(6-amino-9H-purin-9-yl)-2-[({[({[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: 130968
• 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)OP(=O)(O)O)O)N.[Na]
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OCC2OC(C(C2OP(=O)(O)O)O)n2cnc3c2ncnc3N)O)O)OC(C1O)N1C=CCC(=C1)C(=O)N.[Na]
• InChI: InChI=1S/C21H30N7O17P3.Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-15(31)16(44-46(33,34)35)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)14(30)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: JPYVMBKHHSQDKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-2-[({[({[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: [5-(6-aminopurin-9-yl)-2-{[({[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: α-TPNH; α-Triphosphopyridine nucleotide, reduced form; α-Nicotinamide adenine dinucleotide phosphate, reduced sodium salt; α-NADPH

Database IDs

• CAS Number: 108321-28-4
• MDL Number: MFCD00079480
• PubChem SID: 162225246; 24897570
• PubChem CID: 16219732

CALCULATED PROPERTIES

• Acid pKa: 0.82009774
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -10.930757
• LogD (pH = 7.4): -12.542176
• Log P: -6.323914
• Molar Refractivity: 153.8726 cm^3
• Polarizability: 61.291225 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: ≥90% (HPLC)
• Impurities: ≤5% β-isomer

DETAILS

Sigma Aldrich - N2385

Caution
This is not the common NADPH required in the usual enzyme systems.
Other Notes
α analog of β-NADPH