4-(2-amino-3-methoxy-3-oxopropyl)phenyl 6-(6-amino-9H-purin-9-yl)-2-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-7-yl butanedioate

• ChemBase ID: 132370
• Molecular Formular: C24H27N6O11P
• Molecular Mass: 606.478541
• Monoisotopic Mass: 606.14754234
• SMILES: COC(=O)C(Cc1ccc(cc1)OC(=O)CCC(=O)OC1C2C(COP(=O)(O2)O)OC1n1cnc2c1ncnc2N)N
• Canonical SMILES: COC(=O)C(Cc1ccc(cc1)OC(=O)CCC(=O)OC1C2OP(=O)(O)OCC2OC1n1cnc2c1ncnc2N)N
• InChI: InChI=1S/C24H27N6O11P/c1-36-24(33)14(25)8-12-2-4-13(5-3-12)38-16(31)6-7-17(32)40-20-19-15(9-37-42(34,35)41-19)39-23(20)30-11-29-18-21(26)27-10-28-22(18)30/h2-5,10-11,14-15,19-20,23H,6-9,25H2,1H3,(H,34,35)(H2,26,27,28)
• InChIKey: VCGXASLRSBTMRC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-amino-3-methoxy-3-oxopropyl)phenyl 6-(6-amino-9H-purin-9-yl)-2-hydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl butanedioate
• IUPAC Traditional name: 4-(2-amino-3-methoxy-3-oxopropyl)phenyl 6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl butanedioate
• Synonyms: ScAMP-TME; 2′-O-Monosuccinyladenosine 3′:5′-cyclic monophosphate tyrosyl methyl ester

Database IDs

• CAS Number: 104809-08-7
• MDL Number: MFCD00079427
• PubChem SID: 162226647; 24896713
• PubChem CID: 4349612

CALCULATED PROPERTIES

• Acid pKa: 1.8321109
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -1.1377711
• LogD (pH = 7.4): -1.5286317
• Log P: -1.0898949
• Molar Refractivity: 138.7084 cm^3
• Polarizability: 55.411976 Å^3
• Polar Surface Area: 239.53 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ~95%

DETAILS

Sigma Aldrich - M2257

Application
2′-O-Monosuccinyladenosine 3′:5′-cyclic monophosphate tyrosyl methyl ester (ScAMP-TME) is a high specific activity cAMP derivative that binds cAMP-binding antibodies. It may be used in assays, especially radioimmunoassys, for cAMP determination.