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-carbamothioyl-1λ5-pyridin-1-ylium

• ChemBase ID: 132740
• Molecular Formular: C21H27N7O13P2S
• Molecular Mass: 679.490702
• Monoisotopic Mass: 679.08627822
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)OP(=O)([O-])OCC1C(C(C(O1)[n+]1cc(ccc1)C(=S)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(=S)N
• InChI: InChI=1S/C21H27N7O13P2S/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(40-21)6-38-43(35,36)41-42(33,34)37-5-10-13(29)15(31)20(39-10)27-3-1-2-9(4-27)18(23)44/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,44)
• InChIKey: UQYPZLRUJKCREN-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-carbamothioyl-1λ^5-pyridin-1-ylium
• 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-carbamothioyl-1λ^5-pyridin-1-ylium
• Synonyms: Thionicotinamide-DPN; Thionicotinamide adenine dinucleotide

Database IDs

• CAS Number: 4090-29-3
• MDL Number: MFCD00079609
• PubChem SID: 162227017; 24900446
• PubChem CID: 23644511

CALCULATED PROPERTIES

• Acid pKa: 1.8569878
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -10.250685
• LogD (pH = 7.4): -10.515117
• Log P: -9.719985
• Molar Refractivity: 148.8661 cm^3
• Polarizability: 59.371506 Å^3
• Polar Surface Area: 304.02 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%

DETAILS

Sigma Aldrich - T7375

Linkage
Analog of NAD