1-[(2S,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-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

• ChemBase ID: 132057
• Molecular Formular: C21H27N7O14P2
• Molecular Mass: 663.425102
• Monoisotopic Mass: 663.10912184
• SMILES: c1cc(c[n+](c1)[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)n1cnc2c1ncnc2N)O)O)O)O)C(=O)N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2ncnc3N)O)[O-])O[C@@H]([C@@H]1O)[n+]1cccc(c1)C(=O)N
• InChI: InChI=1S/C21H27N7O14P2/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)/t10-,11-,13-,14-,15-,16-,20+,21-/m1/s1
• InChIKey: BAWFJGJZGIEFAR-OPDHFMQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-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
• IUPAC Traditional name: 1-[(2S,3R,4S,5R)-5-[({[(2R,3S,4R,5R)-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
• Synonyms: α-DPN; α-Diphosphopyridine nucleotide; α-NAD; α-Nicotinamide adenine dinucleotide

Database IDs

• CAS Number: 7298-93-3
• EC Number: 230-738-0
• MDL Number: MFCD00134828
• PubChem SID: 162226334; 24897790
• PubChem CID: 16219771

CALCULATED PROPERTIES

• Acid pKa: 1.8569882
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): -11.140584
• LogD (pH = 7.4): -11.40719
• Log P: -10.609851
• 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

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%
• Impurities: <1% β-isomer
• Biological Source: from Saccharomyces cerevisiae

DETAILS

Sigma Aldrich - N6754

Caution
This is not the common NAD required in the usual enzyme systems.
Other Notes
α analog of β-NAD
Application
α-Nicotinamide adenine dinucleotide (αNAD) may be used together with other NAD analogues to study the specificity and kinetics of NAD-dependent and NAD-transporting enzymes and proteins, such as NAD-glycohydrolase(s) and the mitochondrial NAD+ transporter in Saccharomyces cerevisiae.