3-acetyl-1-(5-{[({[3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-1λ5-pyridin-1-ylium

• ChemBase ID: 155191
• Molecular Formular: C22H27N5O15P2
• Molecular Mass: 663.421802
• Monoisotopic Mass: 663.09788845
• SMILES: CC(=O)c1ccc[n+](c1)C1C(C(C(O1)COP(=O)([O-])OP(=O)(O)OCC1C(C(C(O1)n1cnc2c1[nH]cnc2=O)O)O)O)O
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2cnc3c2[nH]cnc3=O)O)[O-])OC(C1O)[n+]1cccc(c1)C(=O)C
• InChI: InChI=1S/C22H27N5O15P2/c1-10(28)11-3-2-4-26(5-11)21-17(31)15(29)12(40-21)6-38-43(34,35)42-44(36,37)39-7-13-16(30)18(32)22(41-13)27-9-25-14-19(27)23-8-24-20(14)33/h2-5,8-9,12-13,15-18,21-22,29-32H,6-7H2,1H3,(H2-,23,24,33,34,35,36,37)
• InChIKey: OFZRVBGRUHGJOH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-acetyl-1-(5-{[({[3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 3-acetyl-1-{5-[({[3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1λ^5-pyridin-1-ylium
• Synonyms: 3-Acetylpyridine hypoxanthine dinucleotide

Database IDs

• CAS Number: 4002-09-9
• MDL Number: MFCD00078884
• PubChem SID: 162249329; 24890966
• PubChem CID: 71312096

CALCULATED PROPERTIES

• Acid pKa: 2.6786666
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -10.213071
• LogD (pH = 7.4): -11.099744
• Log P: -8.016761
• Molar Refractivity: 139.9024 cm^3
• Polarizability: 55.820568 Å^3
• Polar Surface Area: 284.73 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: ~97%
• Empirical Formula (Hill Notation): C22H27N5O15P2

DETAILS

Sigma Aldrich - A5298

Linkage
Analog of β-NAD
Application
3-Acetylpyridine hypoxanthine dinucleotide is an analogue of nicotinamide adenine dinucleotide (NAD) which may be used in mechanistic studies of NAD-dependent enzymes and enzymes that act upon NAD itself.