disodium 1-[(2R,3R,4S,5R)-5-({[({[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2-oxido-2-oxo-tetrahydro-2H-1,3,5,2λ5-furo[3,4-d][1,3,2λ5]dioxaphosphol-4-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ5-pyridin-1-ylium hydrate

• ChemBase ID: 130925
• Molecular Formular: C21H26N7Na2O17P3
• Molecular Mass: 787.368663
• Monoisotopic Mass: 787.03934086
• SMILES: c1cc(c[n+](c1)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@@H]2[C@H]([C@@H](O1)n1cnc3c1ncnc3N)OP(=O)(O2)[O-])O)O)C(=O)N.O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@H]3[C@@H]2OP(=O)(O3)[O-])n2cnc3c2ncnc3N)[O-])[O-])O[C@H]([C@@H]1O)[n+]1cccc(c1)C(=O)N.O.[Na+].[Na+]
• InChI: InChI=1S/C21H26N7O16P3.2Na.H2O/c22-17-12-19(25-7-24-17)28(8-26-12)21-16-15(42-47(36,37)43-16)11(41-21)6-39-46(34,35)44-45(32,33)38-5-10-13(29)14(30)20(40-10)27-3-1-2-9(4-27)18(23)31;;;/h1-4,7-8,10-11,13-16,20-21,29-30H,5-6H2,(H6-,22,23,24,25,31,32,33,34,35,36,37);;;1H2/q;2*+1;/p-2/t10-,11-,13-,14-,15-,16-,20-,21-;;;/m1.../s1
• InChIKey: MIRCUEMBVUDWBT-UHOVGGJYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 1-[(2R,3R,4S,5R)-5-({[({[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2-oxido-2-oxo-tetrahydro-2H-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-4-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium hydrate
• IUPAC Traditional name: disodium 1-[(2R,3R,4S,5R)-5-{[({[(3aR,4R,6R,6aR)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-tetrahydro-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-4-yl]methyl phosphonato}oxyphosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium hydrate
• Synonyms: 2′:3′-Cyclic NADP; β-Nicotinamide adenine dinucleotide 2′:3′-cyclic monophosphate disodium salt hydrate

Database IDs

• CAS Number: 100929-77-9(anhydrous)
• PubChem SID: 24897726; 162225203
• PubChem CID: 16219754

CALCULATED PROPERTIES

• Acid pKa: 1.5041692
• H Acceptors: 15
• H Donor: 4
• LogD (pH = 5.5): -12.702961
• LogD (pH = 7.4): -13.01037
• Log P: -9.773638
• Molar Refractivity: 145.7257 cm^3
• Polarizability: 59.362686 Å^3
• Polar Surface Area: 342.05 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%

DETAILS

Sigma Aldrich - N5257

Other Notes
Analog of β-NADP
Substrates
Useful as a substrate for 3′-phosphodiesterase, 2′:3′-cyclic nucleotide (EC 3.1.4.37).