K252a, protein and CAM kinase inhibitor

Key facts

CAS number

99533-80-9

Purity

>99%

Form

Solid

form

Source

Nocardiopsis sp.

Molecular weight

467.5 Da

Molecular formula

C₂₇H₂₁N₃O₅

PubChem

3035817

Nature

Native

Solubility

Soluble in DMSO to 25 mM

Soluble in ethanol to 5 mM

Biochemical name

Antibiotic K 252a

Biological description

Highly potent, cell-permeable inhibitor of protein kinases such as PKA, PKC, PKG (IC₅₀ = 18-25 nM), Serine/threonine protein kinases (IC₅₀ values are 10-20 nM) and CAM kinase II (K_i = 1.8 nM). Analog of staurosporine (ab120056), exhibits a wide range of effects including neuroprotection and improvement of psoriasis in vivo.

Canonical smiles

CC12C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)(C(=O)OC)O

Isomeric smiles

C[C@@]12[C@](C[C@@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)(C(=O)OC)O

InChi

InChI=1S/C27H21N3O5/c1-26-27(33,25(32)34-2)11-18(35-26)29-16-9-5-3-7-13(16)20-21-15(12-28-24(21)31)19-14-8-4-6-10-17(14)30(26)23(19)22(20)29/h3-10,18,33H,11-12H2,1-2H3,(H,28,31)/t18-,26+,27+/m1/s1

InChiKey

KOZFSFOOLUUIGY-SOLYNIJKSA-N

IUPAC Name

methyl (15S,16R,18R)-16-hydroxy-15-methyl-3-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1,6,8,10,12,20,22,24,26-nonaene-16-carboxylate