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-carboxy-1λ5-pyridin-1-ylium sodium

• ChemBase ID: 132380
• Molecular Formular: C21H26N6NaO15P2
• Molecular Mass: 687.399632
• Monoisotopic Mass: 687.0829067
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)OP(=O)([O-])OCC1C(C(C(O1)[n+]1cc(ccc1)C(=O)O)O)O)O)O)N.[Na]
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2cnc3c2ncnc3N)O)[O-])OC(C1O)[n+]1cccc(c1)C(=O)O.[Na]
• InChI: InChI=1S/C21H26N6O15P2.Na/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(31)14(29)11(41-20)6-39-44(36,37)42-43(34,35)38-5-10-13(28)15(30)19(40-10)26-3-1-2-9(4-26)21(32)33;/h1-4,7-8,10-11,13-16,19-20,28-31H,5-6H2,(H4-,22,23,24,32,33,34,35,36,37)
• InChIKey: SSMFFDBXAUKIMZ-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-carboxy-1λ^5-pyridin-1-ylium sodium
• 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-carboxy-1λ^5-pyridin-1-ylium sodium
• Synonyms: Deamido NAD; NAAD; Nicotinic acid NAD; Nicotinic acid adenine dinucleotide sodium salt

Database IDs

• CAS Number: 104809-30-5
• MDL Number: MFCD00082430
• PubChem SID: 24897698; 162226657
• PubChem CID: 71308553

CALCULATED PROPERTIES

• Acid pKa: 1.8055931
• H Acceptors: 16
• H Donor: 7
• LogD (pH = 5.5): -11.739238
• LogD (pH = 7.4): -12.029734
• Log P: -9.379553
• Molar Refractivity: 139.053 cm^3
• Polarizability: 55.743515 Å^3
• Polar Surface Area: 315.3 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: 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: ≥98%

DETAILS

Sigma Aldrich - N4256

Other Notes
Analog of β-NAD
Application
Nicotinic acid adenine dinucleotide (deamido-NAD, NAAD) is used to study the structure of nicotinate mononucleotide adenylyltransferase(s) (NMN/NaMN). NAAD is used as a substrate to study the specificity and kinetics of nicotinamide adenine dinucleotide synthetase(s) (NADS). NAAD is used as a cosubstrate to study mechanisms of members of the Sir2 class of NAD(+)-dependent deacetylases.