sodium 1-[(2S,3S,4R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ5-pyridin-1-ylium

• ChemBase ID: 134350
• Molecular Formular: C21H26N6NaO18P3
• Molecular Mass: 766.371593
• Monoisotopic Mass: 766.04141219
• SMILES: c1cc(c[n+](c1)[C@@H]1[C@H]([C@H](C(O1)COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)OP(=O)(O)O)O)O)O)C(=O)O.[Na+]
• Canonical SMILES: O[C@H]1[C@@H](O)C(O[C@@H]1[n+]1cccc(c1)C(=O)O)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)(O)O)n1cnc2c1ncnc2N)[O-])[O-].[Na+]
• InChI: InChI=1S/C21H27N6O18P3.Na/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(44-46(33,34)35)14(29)11(43-20)6-41-48(38,39)45-47(36,37)40-5-10-13(28)15(30)19(42-10)26-3-1-2-9(4-26)21(31)32;/h1-4,7-8,10-11,13-16,19-20,28-30H,5-6H2,(H6-,22,23,24,31,32,33,34,35,36,37,38,39);/q;+1/p-1/t10?,11-,13+,14-,15+,16-,19+,20-;/m1./s1
• InChIKey: KKCRODBDXQTAPI-NZNNTXIPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 1-[(2S,3S,4R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: sodium 1-[(2S,3S,4R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ^5-pyridin-1-ylium
• Synonyms: β-NAADP; Nicotinic acid adenine dinucleotide phosphate sodium salt

Database IDs

• CAS Number: 5502-96-5
• MDL Number: MFCD00274064
• PubChem SID: 162228626; 24897746
• PubChem CID: 16219758

CALCULATED PROPERTIES

• Acid pKa: 0.6518583
• H Acceptors: 18
• H Donor: 7
• LogD (pH = 5.5): -14.441434
• LogD (pH = 7.4): -16.141619
• Log P: -9.643525
• Molar Refractivity: 148.8042 cm^3
• Polarizability: 60.219505 Å^3
• Polar Surface Area: 364.66 Å^2
• Rotatable Bonds: 13
• 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: ≥92.5%

DETAILS

Sigma Aldrich - N5655

Other Notes
Note: Should not be confused with nicotinamide adenine dinucleotide phosphate (NADP).
Preparation Note
Enzymatically prepared analog of β-NADP+.
Biochem/physiol Actions
Potent activator of intracellular Ca2+ release via an IP3 and cyclic ADP ribose-independent mechanism.