(4aR,6R,7R,7aS)-6-(6-amino-8-chloro-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-one

• ChemBase ID: 103599
• Molecular Formular: C10H11ClN5O6P
• Molecular Mass: 363.651001
• Monoisotopic Mass: 363.01354741
• SMILES: Clc1nc2c(ncnc2n1[C@@H]1O[C@@H]2COP(=O)(O[C@H]2[C@H]1O)O)N
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1c(Cl)nc2c1ncnc2N
• InChI: InChI=1S/C10H11ClN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
• InChIKey: CLLFEJLEDNXZNR-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aS)-6-(6-amino-8-chloro-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• IUPAC Traditional name: c-amp
• Synonyms: 8-Chloro-cAMP; 8-CHLOROADENOSINE-cyclic-3',5'-MONOPHOSPHATE

Database IDs

• CAS Number: 41941-56-4
• PubChem SID: 162102929
• PubChem CID: 100299

CALCULATED PROPERTIES

• Acid pKa: 1.8291767
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.7682805
• LogD (pH = 7.4): -2.780221
• Log P: -2.478405
• Molar Refractivity: 75.3154 cm^3
• Polarizability: 29.97762 Å^3
• Polar Surface Area: 154.84 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 219°C

Safety Information

• Storage Condition: 0°C
• RTECS: AU7357552

DETAILS

MP Biomedicals - 02152400

An analog of c-AMP that demonstrates novel properties in cell culture, including steroidogenic activity in rat adrenal cells and inhibition of a variety of cancer cells in culture.

REFERENCES

• Free, C.A. and Paik, V.S., Endocrinology, 100: 1287-1293 (1977).
• Tagliaferri, P., et al., Cancer Res., 48: 1642-1650 (1988).