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

• ChemBase ID: 133288
• Molecular Formular: C22H28N6O14P2
• Molecular Mass: 662.437042
• Monoisotopic Mass: 662.11387287
• SMILES: CC(=O)c1ccc[n+](c1)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2ncnc3N)O)[O-])O[C@H]([C@@H]1O)[n+]1cccc(c1)C(=O)C
• InChI: InChI=1S/C22H28N6O14P2/c1-10(29)11-3-2-4-27(5-11)21-17(32)15(30)12(40-21)6-38-43(34,35)42-44(36,37)39-7-13-16(31)18(33)22(41-13)28-9-26-14-19(23)24-8-25-20(14)28/h2-5,8-9,12-13,15-18,21-22,30-33H,6-7H2,1H3,(H3-,23,24,25,34,35,36,37)/t12-,13-,15-,16-,17-,18-,21-,22-/m1/s1
• InChIKey: KPVQNXLUPNWQHM-RBEMOOQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-acetyl-1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 3-acetyl-1-[(2R,3R,4S,5R)-5-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: APAD; 3-Acetylpyridine adenine dinucleotide; 3-Acetylpyridine adenine dinucleotide, reduced form

Database IDs

• CAS Number: 102029-93-6; 86-08-8
• MDL Number: MFCD00078882
• PubChem SID: 162227565; 24890946; 24890959
• PubChem CID: 123926

CALCULATED PROPERTIES

• Acid pKa: 1.8569882
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -10.433578
• LogD (pH = 7.4): -10.700206
• Log P: -9.902844
• Molar Refractivity: 142.1996 cm^3
• Polarizability: 56.99978 Å^3
• Polar Surface Area: 295.07 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; 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: ≥85%; 90-95%
• Empirical Formula (Hill Notation): C22H28N6O14P2

DETAILS

Sigma Aldrich - A5137

Linkage
Analog of NADH

Sigma Aldrich - A5251

Biochem/physiol Actions
APAD is an NAD analog with higher oxidation potential than NAD. It can substitute for NAD as a hydrogen-accepting cofactor in many dehydrogenase reactions; e.g. lactate dehydrogenase from Toxoplasma, Clonorchis, and Plasmodium, bacterial lipoamide dehydrogenase, as well as mammalian dehydrogenases. It can also act as a proton acceptor in various transhydrogenation reactions with NADH or NADPH.
Linkage
Analog of NAD