1-(5-{[({[5-(2-amino-6-oxo-6,9-dihydro-3H-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: 133185
• Molecular Formular: C21H27N7O15P2
• Molecular Mass: 679.424502
• Monoisotopic Mass: 679.10403646
• SMILES: c1nc2c(n1C1C(C(C(O1)COP(=O)(O)OP(=O)([O-])OCC1C(C(C(O1)[n+]1cc(ccc1)C(=O)N)O)O)O)O)[nH]c(nc2=O)N
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n(cn2)C1OC(C(C1O)O)COP(=O)(OP(=O)(OCC1OC(C(C1O)O)[n+]1cccc(c1)C(=O)N)[O-])O
• InChI: InChI=1S/C21H27N7O15P2/c22-16(33)8-2-1-3-27(4-8)19-14(31)12(29)9(41-19)5-39-44(35,36)43-45(37,38)40-6-10-13(30)15(32)20(42-10)28-7-24-11-17(28)25-21(23)26-18(11)34/h1-4,7,9-10,12-15,19-20,29-32H,5-6H2,(H6-,22,23,25,26,33,34,35,36,37,38)
• InChIKey: NCFRZZVNRVEQJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(5-{[({[5-(2-amino-6-oxo-6,9-dihydro-3H-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-{5-[({[5-(2-amino-6-oxo-3H-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
• Synonyms: Nicotinamide guanine dinucleotide sodium salt

Database IDs

• CAS Number: 5624-35-1
• MDL Number: MFCD00079505
• PubChem SID: 162227462; 24897721
• PubChem CID: 71308645

CALCULATED PROPERTIES

• Acid pKa: 1.8573084
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): -11.133242
• LogD (pH = 7.4): -11.598967
• Log P: -7.958216
• Molar Refractivity: 141.8673 cm^3
• Polarizability: 56.196934 Å^3
• Polar Surface Area: 336.77 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

DETAILS

Sigma Aldrich - N5131

Other Notes
Analog of β-NAD
Application
Nicotinamide guanine dinucleotide (NGD+) may be used as a preferred substrate of specific snake Trimeresurus stejnegeri venom phospodiesterase and a substrate to study the specificity and kinetics of ADP-ribosyl cyclase(s).