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

• ChemBase ID: 153694
• 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+;;/m0../s1
• InChIKey: QRGNQKGQENGQSE-QUWMEQBESA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl ({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: disodium [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: β-DPNH; β-NADH; Coenzyme I reduced disodium salt; Diphosphopyridine nucleotide reduced disodium salt; β-Nicotinamide adenine dinucleotide, reduced disodium salt; 还原型 β-烟酰胺腺嘌呤二核苷酸 二钠盐

Database IDs

• CAS Number: 606-68-8
• EC Number: 210-123-3
• MDL Number: MFCD00036200
• Beilstein Number: 5230241
• PubChem SID: 24897900; 24897913; 24897413; 24897793; 24897447; 24897828; 24897788; 24897903; 162247833
• PubChem CID: 16219711

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

Product Information

• Purity: ~98%; ≥98%
• Packaging: pkg of 0.2 mg (per vial); pkg of 0.3 mg (per vial); pkg of 0.5 mg (per vial); pkg of 1 mg (per vial); pkg of 10 mg (per vial); pkg of 2 mg (per vial); pkg of 25-30 mg (per vial); pkg of 5 mg (per vial)
• Empirical Formula (Hill Notation): C21H27N7Na2O14P2

DETAILS

Sigma Aldrich - N9535

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.
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).

Sigma Aldrich - N6660

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.
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).

Sigma Aldrich - N6785

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.
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).

Sigma Aldrich - N9410

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.
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).

Sigma Aldrich - N0161

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.

Sigma Aldrich - N9785

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.

Sigma Aldrich - N7410

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.
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).

Sigma Aldrich - N0786

Biochem/physiol Actions
Electron donor
Other Notes
Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.
Reconstitution
Solutions should be prepared fresh and used promptly.