CHELERYTHRINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H18NO4
Molecular Weight	348.3719
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2C(C=[N+](C)C3=C2C=CC4=CC5=C(OCO5)C=C34)=C1OC

InChI

InChIKey=LLEJIEBFSOEYIV-UHFFFAOYSA-N

InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24380291 | https://www.ncbi.nlm.nih.gov/pubmed/2244923 | https://www.ncbi.nlm.nih.gov/pubmed/12702731 | https://www.ncbi.nlm.nih.gov/pubmed/16936897 | http://www.google.com.pg/patents/WO2002013803A2

Chelerythrine is a kind of benzo[c] phenanthridine alkaloids, which is widely found in plant of Fumariaceae, Papaveraceae, Ranunculaceae and Rutaceae families. Chelerythrine is a potent and specific inhibitor of protein kinase C. In addition chelerythrine inhibits pro-survival protein Bcl(XL) thereby inducing apoptosis. It exerts antitumor properties.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244923	Inhibitor 8297	0.7 µM [Ki]
Apoptosis regulator Bcl-X 8 Target ID: CHEMBL4625 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17011577 \| https://www.ncbi.nlm.nih.gov/pubmed/12702731	Inhibitor 8297
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26183621	Modulator 828	566.0 nM [IC50]
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28509993 \| https://www.ncbi.nlm.nih.gov/pubmed/28102286	Binding Agent 1064
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://adisinsight.springer.com/drugs/800013523	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: http://www.google.com.pg/patents/WO2002013803A2 http://adisinsight.springer.com/drugs/800013523 https://www.ncbi.nlm.nih.gov/pubmed/28515445 https://www.ncbi.nlm.nih.gov/pubmed/28399187	Primary		Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11786500 https://www.ncbi.nlm.nih.gov/pubmed/28842814 https://www.ncbi.nlm.nih.gov/pubmed/26515544 https://www.ncbi.nlm.nih.gov/pubmed/14768516	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
17 beta-estradiol-BSA conjugates and 17 beta-estradiol regulate growth plate chondrocytes by common membrane associated mechanisms involving PKC dependent and independent signal transduction.	2001	11255224
Metalloproteinase activity in growth plate chondrocyte cultures is regulated by 1,25-(OH)(2)D(3) and 24,25-(OH)(2)D(3) and mediated through protein kinase C.	2001 Apr	11334710
Antisense knockout of HOXB4 blocks 1,25-dihydroxyvitamin D3 inhibition of c-myc expression.	2001 Apr	11250656
Local factor production by MG63 osteoblast-like cells in response to surface roughness and 1,25-(OH)2D3 is mediated via protein kinase C- and protein kinase A-dependent pathways.	2001 Apr	11246968
Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices.	2001 Aug	11512036
Use of protein kinase C inhibitors results in rapid [Mg(2+)](i) mobilization in primary cultured rat aortic smooth muscle cells: are certain kinase C isoforms natural homeostatic regulators of cystolic free Mg(2+).	2001 Feb 16	11226406
Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells.	2001 Feb 16	11226388
Benzo[c]phenanthridine bases and their antituberculosis activity.	2001 Jan	11135299
Protein kinase C isoform-dependent myocardial protection by ischemic preconditioning and potassium cardioplegia.	2001 Jan	11135170
Signal pathway involved in the development of hypoxic preconditioning in rat hepatocytes.	2001 Jan	11124829
Protection of cardiac myocytes via delta(1)-opioid receptors, protein kinase C, and mitochondrial K(ATP) channels.	2001 Jan	11123254
Brief rapid pacing depresses contractile function via Ca(2+)/PKC-dependent signaling in cat ventricular myocytes.	2001 Jan	11123222
Evidence for a role of protein kinase C in FGF signal transduction in the developing chick limb bud.	2001 Jul	11493562
Differential effects of protein kinase C on human vascular smooth muscle cell proliferation and migration.	2001 Jul	11406504
A new diprenyl coumarin and alkaloids from the bark of Zanthoxylum dimorphophyllum (Rutaceae).	2001 Jul-Aug	11531078
Protein kinase A- and C-dependent modulation of murine inducible nitric oxide synthase.	2001 Jun	11642342
Inhibition of carbachol stimulated acid secretion by interleukin 1beta in rabbit parietal cells requires protein kinase C.	2001 Jun	11358895
Protein kinase C and intracellular calcium are required for amphetamine-mediated dopamine release via the norepinephrine transporter in undifferentiated PC12 cells.	2001 Jun	11356924
Signal transduction of flumazenil-induced preconditioning in myocytes.	2001 Mar	11179070
Protein kinase C inhibition abrogates hepatic ischemic preconditioning responses.	2001 May 15	11341790
Capsaicin potentiates 1,25-dihydoxyvitamin D3- and all-trans retinoic acid-induced differentiation of human promyelocytic leukemia HL-60 cells.	2001 May 25	11408028
Activation of PKC decreases myocardial O2 consumption and increases contractile efficiency in rats.	2001 Nov	11668082
Mechanisms of the apoptotic and necrotic actions of trimethyltin in cerebellar granule cells.	2001 Nov	11606804
Regulation of ATP-sensitive K(+) channels by protein kinase C in murine colonic myocytes.	2001 Sep	11502563
A diacylglycerol-activated Ca2+ channel in PC12 cells (an adrenal chromaffin cell line) correlates with expression of the TRP-6 (transient receptor potential) protein.	2001 Sep 15	11535132

Patents

Sample Use Guides

In Vivo Use Guide

Mice injected i.p. with chelerythrine 1-10 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

10 ug/mL of chelerythrine is capable of inducing apoptosis in Dalton's lymphoma (DL) cells.

Name

Type

Language

CHELERYTHRINE

Common Name

English

(1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDINIUM, 1,2-DIMETHOXY-12-METHYL-

Systematic Name

English

CHELERYTHRINE [MI]

Common Name

English

TODDALIN

Common Name

English

1,2-DIMETHOXY-12-METHYL(1,3)DIOXOLO)4',5':4,5)BENZO(1,2-C)PHENANTHRIDINIUM

Common Name

English

CHELERITRINE

Common Name

English

TODDALINE

Common Name

English

BROUSSONPAPYRINE

Common Name

English

Chelerythrine [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

E3B045W6X0