Penitrem A, blocker of KCa1.1

Key facts

CAS number

12627-35-9

Purity

>98%

Form

Solid

form

Source

Penicillium palitans

Molecular weight

634.2 Da

Molecular formula

C₃₇H₄₄ClNO₆

PubChem

44450809

Nature

Native

Solubility

Soluble in DMSO to 10 mM

Biochemical name

(1S,2R,5S,6R,8S,9S,10R,12S,15R,16S,25R,27S,28R)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-prop-1-en-2-yl-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol

Biological description

Potent, selective BK_Ca blocker (IC₅₀ values are 6 and 60 nM for α-subunit and mixed α- and β₁-subunit containing channels respectively). No effect on native delayed rectifier K⁺ currents, cloned voltage-dependent K_v1.5 channels, or K_ATP currents. Inhibits BK channels in inside-out and cell-attached patches. Tremorgenic effects and increases total peripheral resistance in vivo. Orally active.

Canonical smiles

CC(=C)C1C(C2C3(O2)C(O1)CCC4(C3(CCC5C4(C6=C7C5OC(C8CC9C8(C1=C7C(=CC(=C1CC9=C)Cl)N6)O)(C)C)C)O)C)O

Isomeric smiles

CC(=C)[C@@H]1[C@@H]([C@H]2[C@]3(O2)[C@@H](O1)CC[C@]4([C@]3(CC[C@@H]5[C@@]4(C6=C7[C@H]5OC([C@H]8C[C@H]9[C@@]8(C1=C7C(=CC(=C1CC9=C)Cl)N6)O)(C)C)C)O)C)O

InChi

InChI=1S/C37H44ClNO6/c1-15(2)28-27(40)31-37(45-31)23(43-28)9-10-33(6)34(7)18(8-11-35(33,37)41)29-25-24-21(39-30(25)34)14-20(38)17-12-16(3)19-13-22(32(4,5)44-29)36(19,42)26(17)24/h14,18-19,22-23,27-29,31,39-42H,1,3,8-13H2,2,4-7H3/t18-,19+,22+,23-,27-,28+,29-,31-,33+,34+,35-,36+,37+/m0/s1

InChiKey

JDUWHZOLEDOQSR-OBPHCMCKSA-N

IUPAC Name

(1S,2R,5S,6R,8S,9S,10R,12S,15R,16S,25R,27S,28R)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-prop-1-en-2-yl-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol