disodium [(2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl ({[(2R,3S,4R,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 134179
• Molecular Formular: C21H27N7Na2O14P2
• Molecular Mass: 709.404642
• Monoisotopic Mass: 709.0886604
• 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)O)N.[Na+].[Na+]
• 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)O)n1cnc2c1ncnc2N)[O-])[O-].[Na+].[Na+]
• InChI: InChI=1S/C21H29N7O14P2.2Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33;;/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25);;/q;2*+1/p-2/t10-,11+,13-,14+,15-,16+,20+,21+;;/m1../s1
• InChIKey: QRGNQKGQENGQSE-WPVKCSLBSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl ({[(2R,3S,4R,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: disodium [(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R,3S,4R,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: α-DPNH; α-Dihydrodiphosphopyridine nucleotide; α-Dihydronicotinamide adenine dinucleotide; α-NADH; α-Nicotinamide adenine dinucleotide, reduced disodium salt

Database IDs

• CAS Number: 108321-31-9
• MDL Number: MFCD00079521
• PubChem SID: 162228456; 24897797
• PubChem CID: 16219773

CALCULATED PROPERTIES

• Acid pKa: -8.055352
• H Acceptors: 16
• H Donor: 6
• LogD (pH = 5.5): -8.287102
• LogD (pH = 7.4): -8.577429
• Log P: -6.6937094
• Molar Refractivity: 140.7563 cm^3
• Polarizability: 56.47071 Å^3
• Polar Surface Area: 323.28 Å^2
• Rotatable Bonds: 11
• 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%
• Impurities: ≤3% β-isomer

DETAILS

Sigma Aldrich - N6879

Caution
This is not the common NADH required in the usual enzyme systems.
Other Notes
Analog of β-NADH, chemically reduced
Application
α-Nicotinamide adenine dinucleotide, reduced (α-NADH) may be used as a cosubstrate to assess the specificity and kinetics of NAD+/NADH and NADP+/NADPH dependent enzymes and to assess the dynamics of nucleotides in ion channels such as voltage-dependent mitochondrial ion channels (VDAC).