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-formyl-1λ5-pyridin-1-ylium

• ChemBase ID: 131265
• Molecular Formular: C21H26N6O14P2
• Molecular Mass: 648.410462
• Monoisotopic Mass: 648.0982228
• 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)N
• Canonical SMILES: O=Cc1ccc[n+](c1)C1OC(C(C1O)O)COP(=O)(OP(=O)(OCC1OC(C(C1O)O)n1cnc2c1ncnc2N)O)[O-]
• InChI: InChI=1S/C21H26N6O14P2/c22-18-13-19(24-8-23-18)27(9-25-13)21-17(32)15(30)12(40-21)7-38-43(35,36)41-42(33,34)37-6-11-14(29)16(31)20(39-11)26-3-1-2-10(4-26)5-28/h1-5,8-9,11-12,14-17,20-21,29-32H,6-7H2,(H3-,22,23,24,33,34,35,36)
• InChIKey: SZBYQPGZRAWXKJ-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-formyl-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-formyl-1λ^5-pyridin-1-ylium
• Synonyms: 3-Pyridinealdehyde-DPN; 3-Pyridinealdehyde adenine dinucleotide

Database IDs

• CAS Number: 86-07-7
• MDL Number: MFCD00079227
• PubChem SID: 162225543; 24898283
• PubChem CID: 71308414

CALCULATED PROPERTIES

• Acid pKa: 1.8569878
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -10.278721
• LogD (pH = 7.4): -10.545351
• Log P: -9.7479925
• Molar Refractivity: 138.3808 cm^3
• Polarizability: 55.197624 Å^3
• Polar Surface Area: 295.07 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%

DETAILS

Sigma Aldrich - P2171

Linkage
Analog of NAD
Application
3-Pyridinealdehyde adenine dinucleotide is an analogue of NAD that may be used to study the structure and function of NAD binding enzymes such as glyceraldehyde 3-phosphate dehydrogenase, NAD malic enzymes, lactate dehydrogenase and saccharopine dehydrogenase from S. cerevisiae.