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: 132744
• Molecular Formular: C10H11ClN5O6P
• Molecular Mass: 363.651001
• Monoisotopic Mass: 363.01354741
• SMILES: c1nc(c2c(n1)n(c(n2)Cl)C1C(C2C(O1)COP(=O)(O2)O)O)N
• Canonical SMILES: OC1C2OP(=O)(O)OCC2OC1n1c(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)
• InChIKey: CLLFEJLEDNXZNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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: 6-(6-amino-8-chloropurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• Synonyms: 8-Chloro-cAMP; 8-Chloroadenosine 3′,5′-monophosphate; 8-Cl-cAMP; 8-Chloroadenosine 3′,5′-cyclic-monophosphate

Database IDs

• CAS Number: 41941-56-4
• MDL Number: MFCD00153938
• PubChem SID: 24892338; 162227021
• PubChem CID: 323587

CALCULATED PROPERTIES

• Acid pKa: 1.8291711
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.7682736
• LogD (pH = 7.4): -2.780221
• Log P: -2.4781573
• 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

• Solubility: aqueous base: soluble

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85%

DETAILS

Sigma Aldrich - C1081

Biochem/physiol Actions
Membrane-permeable cAMP analog; resistant to hydrolysis by phosphodiesterases.