8-(4-Chlorophenylthio)adenosine 3',5'-cyclic monophosphate (8-CPT-cAMP), Cell permeable cAMP analog.

Key facts

CAS number

93882-12-3

Purity

>99%

Form

Solid

form

Molecular weight

493.8 Da

Molecular formula

C₁₆H₁₄ClN₅NaO₆PS

PubChem

23672705

Nature

Synthetic

Solubility

Soluble in water to 50 mM

Biochemical name

8-Cpt-camp

Biological description

Membrane permeable, lipophilic, cAMP analog. Activator of Epac, cAMP and cGMP-dependent protein kinases (PKA/PKG). Displays site selectivity for Site B of cAMP-dependent PKA type II. Potently inhibits cyclic GMP-specific phosphodiesterase (PDE Va), PDE III and PDE IV (IC₅₀ values are 0.9, 24 and 25 μM, respectively). Increases heart rate, causes fall in arterial blood pressure and vascular resistance in vivo.

Canonical smiles

C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3SC5=CC=C(C=C5)Cl)N)O)OP(=O)(O1)[O-].[Na+]

Isomeric smiles

C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=NC=NC(=C4N=C3SC5=CC=C(C=C5)Cl)N)O)OP(=O)(O1)[O-].[Na+]

InChi

InChI=1S/C16H15ClN5O6PS.Na/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(27-15)5-26-29(24,25)28-12;/h1-4,6,9,11-12,15,23H,5H2,(H,24,25)(H2,18,19,20);/q;+1/p-1/t9-,11-,12-,15-;/m1./s1

InChiKey

YIJFVHMIFGLKQL-DNBRLMRSSA-M

IUPAC Name

sodium;(4aR,6R,7R,7aS)-6-[6-amino-8-(4-chlorophenyl)sulfanylpurin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol