Balanol

Modify Date: 2024-01-03 11:12:47

Balanol Structure
Balanol structure
Common Name Balanol
CAS Number 63590-19-2 Molecular Weight 550.51300
Density 1.62g/cm3 Boiling Point 935.9ºC at 760 mmHg
Molecular Formula C28H26N2O10 Melting Point N/A
MSDS N/A Flash Point 519.8ºC

 Use of Balanol


Balanol (Ophiocordin; Azepinostatin) is a potent and ATP competitive PKC/PKA inhibitor against human PKC isozymes α, β-I, β-II, γ, δ, ε, η (IC50s=4-9 nM) and ζ (IC50=150 nM). Balanol also blocks the phosphorylation of cyclic AMP response element-binding protein (CREB) and myristoylated alanine-rich C kinase substrate (MARCKS). Balanol can be isolated from the fungus Verticillium balanoides[1][2].

 Names

Name (4Z)-4-[(2-carboxy-6-hydroxyphenyl)-hydroxymethylidene]-3-hydroxy-1-[(3R,4R)-3-[(4-hydroxybenzoyl)amino]-2,3,4,5-tetrahydro-1H-azepin-4-yl]-5-oxocyclohex-2-ene-1-carboxylic acid
Synonym More Synonyms

 Balanol Biological Activity

Description Balanol (Ophiocordin; Azepinostatin) is a potent and ATP competitive PKC/PKA inhibitor against human PKC isozymes α, β-I, β-II, γ, δ, ε, η (IC50s=4-9 nM) and ζ (IC50=150 nM). Balanol also blocks the phosphorylation of cyclic AMP response element-binding protein (CREB) and myristoylated alanine-rich C kinase substrate (MARCKS). Balanol can be isolated from the fungus Verticillium balanoides[1][2].
Related Catalog
Target

Human PKCα:4-9 nM ()

PKC-βI:4-9 nM ()

PKC-βII:4-9 nM ()

Human PKCγ:4-9 nM ()

Human PKCδ:4-9 nM ()

Human PKCε:4-9 nM ()

human PKCη:150 nM ()

PKA

In Vitro Balanol (3 μM; 45 min) 抑制 PKA,表现为抑制异丙肾上腺素 (HY-B0468) 对新生大鼠肌细胞A431中荧光素酶活性的诱导作用[1]。 Balanol (10 μM; 45 min) 抑制 A431 细胞中 CREB 和 MARCKS 的磷酸化[1]。
References

[1]. Gustafsson AB, et al. Differential and selective inhibition of protein kinase A and protein kinase C in intact cells by balanol congeners. Mol Pharmacol. 1999 Aug;56(2):377-82.  

[2]. Kulanthaivel P, et al. Balanol: a novel and potent inhibitor of protein kinase C from the fungus Verticillium balanoides. Journal of the American Chemical Society, 1993, 115(14): 6452-6453.

 Chemical & Physical Properties

Density 1.62g/cm3
Boiling Point 935.9ºC at 760 mmHg
Molecular Formula C28H26N2O10
Molecular Weight 550.51300
Flash Point 519.8ºC
Exact Mass 550.15900
PSA 202.72000
LogP 2.86530
Index of Refraction 1.746

 Synonyms

Benzoic acid,4-(2-(((hexahydro-4-((4-hydroxybenzoyl)oxy)-1H-azepin-3-yl)amino)carbonyl)-6-hydroxybenzoyl)-3,5-dihydroxy
Ophiocordin