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=C3C=C5OCOC5=C4)=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

Molecular Formula	C21H18NO4
Molecular Weight	348.3719
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8504	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 8504
Peroxisome proliferator-activated receptor gamma 118 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26183621	Modulator 846	566.0 nM [IC50]
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28509993 \| https://www.ncbi.nlm.nih.gov/pubmed/28102286	Binding Agent 1076
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://adisinsight.springer.com/drugs/800013523	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 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 619 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
Role of protein kinase C in the signal pathways that link Na+/K+-ATPase to ERK1/2.	2001-11-09	11562372
Differentiation of bipolar CG-4 line oligodendrocytes is associated with regulation of CREB, MAP kinase and PKC signalling pathways.	2001-11	11672834
Activation of PKC decreases myocardial O2 consumption and increases contractile efficiency in rats.	2001-11	11668082
Mechanisms of the apoptotic and necrotic actions of trimethyltin in cerebellar granule cells.	2001-11	11606804
Novel role of macrophage migration inhibitory factor in angiotensin II regulation of neuromodulation in rat brain.	2001-11	11606427
Differential MAP kinase activation and Na(+)/H(+) exchanger phosphorylation by H(2)O(2) in rat cardiac myocytes.	2001-11	11600417
Adenosine A(2A) and A(2B) receptor activation of erythropoietin production.	2001-11	11592940
Characterization of the signal transduction pathways mediating morphine withdrawal-stimulated c-fos expression in hypothalamic nuclei.	2001-10-26	11698063
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro.	2001-10-08	11695703
Chelerythrine rapidly induces apoptosis through generation of reactive oxygen species in cardiac myocytes.	2001-10	11603925
Death by protein kinase C inhibitor: a stressful event.	2001-10	11603920
Endothelium-derived endothelin-1 reduces cerebral artery sensitivity to nitric oxide by a protein kinase C-independent pathway.	2001-10	11588325
Protein kinase C and changes in manganese superoxide dismutase gene expression in cultured glial cells.	2001-10	11553022
Role of Na(+)/H(+) exchanger during O(2) deprivation in mouse CA1 neurons.	2001-10	11546657
Regulation and distribution of MAdCAM-1 in endothelial cells in vitro.	2001-10	11546645
Protein kinase C regulation of cell spreading in the molluscan Biomphalaria glabrata embryonic (Bge) cell line.	2001-09-26	11583819
A diacylglycerol-activated Ca2+ channel in PC12 cells (an adrenal chromaffin cell line) correlates with expression of the TRP-6 (transient receptor potential) protein.	2001-09-15	11535132
Protein kinase C regulates dopamine D4 receptor-mediated phospholipid methylation.	2001-09-14	11557258
A new diprenyl coumarin and alkaloids from the bark of Zanthoxylum dimorphophyllum (Rutaceae).	2001-09-04	11531078
The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes.	2001-09	11549349
Src and multiple MAP kinase activation in cardiac hypertrophy and congestive heart failure under chronic pressure-overload: comparison with acute mechanical stretch.	2001-09	11549343
Role of calcineurin in insulin-like growth factor-1-induced hypertrophy of cultured adult rat ventricular myocytes.	2001-09	11548882
Mechanism of action of angiotensin II in human isolated subcutaneous resistance arteries.	2001-09	11522611
Regulation of ATP-sensitive K(+) channels by protein kinase C in murine colonic myocytes.	2001-09	11502563
Induction of osteoblast differentiation indexes by PTHrP in MG-63 cells involves multiple signaling pathways.	2001-09	11500304
Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices.	2001-08	11512036
The effects of isoflurane on native and chimeric muscarinic acetylcholine receptors: the role of protein kinase C.	2001-08	11473864
Diminished alpha1-adrenergic-mediated contraction and translocation of PKC in senescent rat heart.	2001-08	11454560
Inhibition of acetylcholine-activated K(+) current by chelerythrine and bisindolylmaleimide I in atrial myocytes from mice.	2001-07-27	11672559
Chelerythrine and genistein inhibit the endothelin-1-induced increase in myofilament Ca(2+) sensitivity in rabbit ventricular myocytes.	2001-07-20	11476754
Opioid receptor stimulation acts as mediator of protection in ischaemic preconditioning.	2001-07-12	11447487
Evidence for a role of protein kinase C in FGF signal transduction in the developing chick limb bud.	2001-07	11493562
Backtable heat-enhanced preconditioning: a simple and effective means of improving function of heart transplants.	2001-07	11465162
Role of protein kinase C in the reduction of infarct size by N-methyl-1-deoxynojirimycin, an alpha-1,6-glucosidase inhibitor.	2001-07	11429386
Activation of extracellular signal-regulated kinase in trabecular meshwork cells.	2001-07	11428860
Histamine increases interstitial adenosine concentration via activation of ecto-5'-nucleotidase in rat hearts in vivo.	2001-07	11408527
Differential effects of protein kinase C on human vascular smooth muscle cell proliferation and migration.	2001-07	11406504
Heat shock prevents simulated ischemia-induced apoptosis in renal tubular cells via a PKC-dependent mechanism.	2001-07	11404313
ANG II-mediated inhibition of neuronal delayed rectifier K+ current: role of protein kinase C-alpha.	2001-07	11401823
Post-ischemic PKC inhibition impairs myocardial calcium handling and increases contractile protein calcium sensitivity.	2001-07	11399253
Involvement of protein kinase C and tyrosine kinase in lipopolysaccharide-induced anorexia.	2001-06-23	11420064
Protein kinase A- and C-dependent modulation of murine inducible nitric oxide synthase.	2001-06	11642342
Stathmin levels in growth plate chondrocytes are modulated by vitamin D3 metabolites and transforming growth factor-beta1 and are associated with proliferation.	2001-06	11572331
Role of protein kinase C and phosphatases in the pulmonary vasculature of neonatal piglets.	2001-06	11395610
Vasopressin-induced protein kinase C-dependent superoxide generation contributes to atp-sensitive potassium channel but not calcium-sensitive potassium channel function impairment after brain injury.	2001-06	11387506
Capsaicin potentiates 1,25-dihydoxyvitamin D3- and all-trans retinoic acid-induced differentiation of human promyelocytic leukemia HL-60 cells.	2001-05-25	11408028
Stimulatory effect of isoferulic acid on alpha1A-adrenoceptor to increase glucose uptake into cultured myoblast C2C12 cell of mice.	2001-05-14	11474559
Protein phosphorylation in mitochondria from human placenta.	2001-05	11373154
High calcium and dobutamine positive inotropy in the perfused mouse heart: myofilament calcium responsiveness, energetic economy, and effects of protein kinase C inhibition.	2001	11553322
Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.	2001	11504450

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:59:42 GMT 2025` Edited by `admin` on `Mon Mar 31 19:59:42 GMT 2025`
Record UNII	E3B045W6X0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHELERYTHRINE

Common Name

English

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

Preferred 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

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