1-(5-{[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-3-carbamoyl-1λ5-pyridin-1-ylium lithium

• ChemBase ID: 134339
• Molecular Formular: C21H27LiN7O14P2
• Molecular Mass: 670.366102
• Monoisotopic Mass: 670.12512639
• SMILES: [Li].c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)OP(=O)([O-])OCC1C(C(C(O1)[n+]1cc(ccc1)C(=O)N)O)O)O)O)N
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2cnc3c2ncnc3N)O)[O-])OC(C1O)[n+]1cccc(c1)C(=O)N.[Li]
• InChI: InChI=1S/C21H27N7O14P2.Li/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;/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)
• InChIKey: BSBXSNLPTFPMHS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(5-{[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-3-carbamoyl-1λ^5-pyridin-1-ylium lithium
• IUPAC Traditional name: 1-{5-[({[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-3-carbamoyl-1λ^5-pyridin-1-ylium lithium
• Synonyms: DPN; NAD; Nadide; β-DPN; β-NAD; β-Nicotinamide adenine dinucleotide lithium salt from Saccharomyces cerevisiae; 二磷酸吡啶核苷酸; 辅酶 1; 辅酶; β-烟酰胺腺嘌呤二核苷酸 锂盐 来源于酿酒酵母

Database IDs

• CAS Number: 64417-72-7
• EC Number: 264-884-1
• MDL Number: MFCD00036974
• PubChem SID: 162228615; 24897811
• PubChem CID: 71308791

CALCULATED PROPERTIES

• Acid pKa: 1.8569878
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): -11.140582
• LogD (pH = 7.4): -11.40719
• Log P: -10.609855
• Molar Refractivity: 140.8752 cm^3
• Polarizability: 56.19417 Å^3
• Polar Surface Area: 321.09 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

Pharmacology Properties

• Gene Information: human ... ESR1(2099), ESR2(2100)

Product Information

• Purity: ≥95%

DETAILS

Sigma Aldrich - N7132

Biochem/physiol Actions
Electron acceptor
Other Notes
This is the common form of NAD.
Application
β-Nicotinamide adenine dinucleotide (NAD+) and β-Nicotinamide adenine dinucleotide, reduced (NADH) comprise a coenzyme redox pair (NAD+:NADH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. In addition to its redox function, NAD+/NADH is a donor of ADP-ribose units in ADP-ribosylaton (ADP-ribosyltransferases; poly(ADP-ribose) polymerases ) reactions and a precursor of cyclic ADP-ribose (ADP-ribosyl cyclases).