[({[5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy})phosphinic acid

• ChemBase ID: 153220
• Molecular Formular: C21H28N6O15P2
• Molecular Mass: 666.425742
• Monoisotopic Mass: 666.10878749
• SMILES: c1[nH]c2c(c(=O)n1)ncn2C1C(C(C(O1)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N1C=CCC(=C1)C(=O)N)O)O)O)O
• Canonical SMILES: OC1C(O)C(OC1N1C=CCC(=C1)C(=O)N)COP(=O)(OP(=O)(OCC1OC(C(C1O)O)n1cnc2c1[nH]cnc2=O)O)O
• InChI: InChI=1S/C21H28N6O15P2/c22-17(32)9-2-1-3-26(4-9)20-15(30)13(28)10(40-20)5-38-43(34,35)42-44(36,37)39-6-11-14(29)16(31)21(41-11)27-8-25-12-18(27)23-7-24-19(12)33/h1,3-4,7-8,10-11,13-16,20-21,28-31H,2,5-6H2,(H2,22,32)(H,34,35)(H,36,37)(H,23,24,33)
• InChIKey: WXWNHSQIXJHVJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy})phosphinic acid
• IUPAC Traditional name: {[5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphinic acid
• Synonyms: Deamino DPNH; Deamino NADH; Deaminodiphosphopyridine nucleotide, reduced form; Nicotinamide hypoxanthine dinucleotide, reduced form, sodium salt

Database IDs

• MDL Number: MFCD00057030
• PubChem SID: 162247359; 24897791
• PubChem CID: 4066204

CALCULATED PROPERTIES

• Acid pKa: 2.0940907
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): -8.076186
• LogD (pH = 7.4): -8.976708
• Log P: -4.282444
• Molar Refractivity: 140.7025 cm^3
• Polarizability: 55.533653 Å^3
• Polar Surface Area: 307.28 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: ≥95%
• Type: Grade I
• Empirical Formula (Hill Notation): C21H28N6O15P2 · xNa+

DETAILS

Sigma Aldrich - N6756

Other Notes
Analog of β-NADH
Preparation Note
Enzymatically reduced.
Application
Nicotinamide hypoxanthine dinucleotide, reduced (deamino-NADH) may be used study the specificity and kinetics of NADH: ubiquinone oxidoreductase(s).