({[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-[2-(methylamino)benzoyloxy]oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

• ChemBase ID: 173030
• Molecular Formular: C18H23N6O14P3
• Molecular Mass: 640.328303
• Monoisotopic Mass: 640.04850934
• SMILES: n1cnc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)COP(=O)(O)OP(=O)(OP(=O)(O)O)O)O)OC(=O)c1c(cccc1)NC
• Canonical SMILES: CNc1ccccc1C(=O)OC1[C@@H](O)[C@H](O[C@H]1n1cnc2c1ncnc2N)COP(=O)(OP(=O)(OP(=O)(O)O)O)O
• InChI: InChI=1S/C18H23N6O14P3/c1-20-10-5-3-2-4-9(10)18(26)36-14-13(25)11(6-34-40(30,31)38-41(32,33)37-39(27,28)29)35-17(14)24-8-23-12-15(19)21-7-22-16(12)24/h2-5,7-8,11,13-14,17,20,25H,6H2,1H3,(H,30,31)(H,32,33)(H2,19,21,22)(H2,27,28,29)/t11-,13+,14?,17-/m1/s1
• InChIKey: OTIXVXNMFVNGEF-NUKIEUHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-[2-(methylamino)benzoyloxy]oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-[2-(methylamino)benzoyloxy]oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: MANT-ATP; 2'-(N-Methylanthraniloyl)adenosine Triphosphate, Sodium Salt DISCONTINUED

Database IDs

• PubChem SID: 164228940
• PubChem CID: 71750111

CALCULATED PROPERTIES

• Acid pKa: 0.8704412
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): -7.200022
• LogD (pH = 7.4): -7.8515625
• Log P: -3.6490438
• Molar Refractivity: 135.8301 cm^3
• Polarizability: 52.91272 Å^3
• Polar Surface Area: 297.23 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Slightly Sol. in Methanol; Water
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - M288050

A blue fluorescent derivative of cGMP is a useful substrate the assay of cyclic nucleotide phosphdiesterase. Also inhibits calmodulin-dependent activation of cyclic nucleotide phosphodiesterase by peptide segments of HIV envelope glycoproteins has been m

REFERENCES

• J. Biol. Chem., 257, 13354 (1982)
• Anal. Biochem., 162, 291 (1982)
• J. Biol. Chem., 270, 22277 (1993)