1-[(2R,3S,5R)-5-{[({[(4R,6R,6aS)-6-(6-amino-9H-purin-9-yl)-2-hydroxy-2-oxo-tetrahydro-2H-1,3,5,2λ5-furo[3,4-d][1,3,2λ5]dioxaphosphol-4-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ5-pyridin-1-ylium

• ChemBase ID: 165233
• Molecular Formular: C21H26N7O16P3
• Molecular Mass: 725.389723
• Monoisotopic Mass: 725.06488768
• SMILES: C([C@@H]1C2OP(=O)(O[C@@H]2[C@@H](O1)n1c2c(nc1)c(ncn2)N)O)OP(=O)(OP(=O)(OC[C@@H]1C([C@@H]([C@@H](O1)[n+]1cc(ccc1)C(=O)N)O)O)[O-])O
• Canonical SMILES: O[C@H]1C(O)[C@H](O[C@H]1[n+]1cccc(c1)C(=O)N)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]2C1OP(=O)(O2)O)n1cnc2c1ncnc2N)O)[O-]
• InChI: InChI=1S/C21H26N7O16P3/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)/t10-,11-,13?,14+,15?,16+,20-,21-/m1/s1
• InChIKey: FYSCLQKJEHBMFH-SDQJTPJCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3S,5R)-5-{[({[(4R,6R,6aS)-6-(6-amino-9H-purin-9-yl)-2-hydroxy-2-oxo-tetrahydro-2H-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-4-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3S,5R)-5-[({[(4R,6R,6aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-tetrahydro-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-4-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• Synonyms: Adenosine 5'-(Trihydrogen Diphosphate) Cyclic 2',3'-(Hydrogen Phosphate) P'→5'-Ester with 3-(Aminocarbonyl)-1-β-D-ribofuranosylpyridinium Inner Salt; 2'3'-Cyclic-NADP

Database IDs

• CAS Number: 62640-02-2
• PubChem SID: 162259366
• PubChem CID: 71315093

CALCULATED PROPERTIES

• Acid pKa: 1.5041692
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -12.702961
• LogD (pH = 7.4): -13.01037
• Log P: -9.773638
• Molar Refractivity: 147.9691 cm^3
• Polarizability: 59.599625 Å^3
• Polar Surface Area: 336.39 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C988350

2'3'-Cyclic-NADP as a substrate for 2',3'-cyclic nucleotide 3'-phosphodiesterase. 2',3'-Cyclic nucleotide 3'-phosphodiesterase (CNPase) was isolated from bovine brain white matter by a rapid procedure.

REFERENCES

• Stephon, R.L., et al.: Anal. Biochem., 202, 6 (1992)