CHELERYTHRINE HYDROXIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H18NO4.HO
Molecular Weight	365.3793
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[OH-].COC1=CC=C2C(C=[N+](C)C3=C2C=CC4=C3C=C5OCOC5=C4)=C1OC

InChI

InChIKey=YZYNINHQZLUUAW-UHFFFAOYSA-M

InChI=1S/C21H18NO4.H2O/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;1H2/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	HO
Molecular Weight	17.0073
Charge	-1
Count

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

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 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
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
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
Receptor-stimulated phospholipase A(2) liberates arachidonic acid and regulates neuronal excitability through protein kinase C.	2001 Apr	11287487
Ca2+-induced contraction of cat esophageal circular smooth muscle cells.	2001 Apr	11245615
Excitation-contraction coupling in pulmonary vascular smooth muscle involves tyrosine kinase and Rho kinase.	2001 Apr	11238006
Hormonal regulation of phospholipase D activity in Ca(2+) transporting cells of rabbit connecting tubule and cortical collecting duct.	2001 Apr 23	11336804
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
Opioid receptor stimulation acts as mediator of protection in ischaemic preconditioning.	2001 Feb-Mar	11447487
Evidence for a role of protein kinase C in FGF signal transduction in the developing chick limb bud.	2001 Jul	11493562
Role of protein kinase C in the reduction of infarct size by N-methyl-1-deoxynojirimycin, an alpha-1,6-glucosidase inhibitor.	2001 Jul	11429386
Histamine increases interstitial adenosine concentration via activation of ecto-5'-nucleotidase in rat hearts in vivo.	2001 Jul	11408527
Differential effects of protein kinase C on human vascular smooth muscle cell proliferation and migration.	2001 Jul	11406504
Heat shock prevents simulated ischemia-induced apoptosis in renal tubular cells via a PKC-dependent mechanism.	2001 Jul	11404313
ANG II-mediated inhibition of neuronal delayed rectifier K+ current: role of protein kinase C-alpha.	2001 Jul	11401823
Chelerythrine and genistein inhibit the endothelin-1-induced increase in myofilament Ca(2+) sensitivity in rabbit ventricular myocytes.	2001 Jul 20	11476754
Inhibition of acetylcholine-activated K(+) current by chelerythrine and bisindolylmaleimide I in atrial myocytes from mice.	2001 Jul 27	11672559
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
Stathmin levels in growth plate chondrocytes are modulated by vitamin D3 metabolites and transforming growth factor-beta1 and are associated with proliferation.	2001 Jun	11572331
Role of protein kinase C and phosphatases in the pulmonary vasculature of neonatal piglets.	2001 Jun	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 Jun	11387506
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
Protein phosphorylation in mitochondria from human placenta.	2001 May	11373154
CAMKII inhibition in the parabrachial nuclei elicits conditioned taste aversion in rats.	2001 May	11300732
Anti-adrenergic effect of adenosine on Na(+)-Ca(2+) exchange current recorded from guinea-pig ventricular myocytes.	2001 May	11292391
Responsiveness of canine bronchial vasculature to excitatory stimuli and to cooling.	2001 May	11290517
17beta-oestradiol stimulates capacitative Ca2+ entry in human endometrial cells.	2001 May 15	11369445
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
Involvement of protein kinase C and tyrosine kinase in lipopolysaccharide-induced anorexia.	2001 May-Jun	11420064
Differentiation of bipolar CG-4 line oligodendrocytes is associated with regulation of CREB, MAP kinase and PKC signalling pathways.	2001 Nov	11672834
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
Novel role of macrophage migration inhibitory factor in angiotensin II regulation of neuromodulation in rat brain.	2001 Nov	11606427
Differential MAP kinase activation and Na(+)/H(+) exchanger phosphorylation by H(2)O(2) in rat cardiac myocytes.	2001 Nov	11600417
Adenosine A(2A) and A(2B) receptor activation of erythropoietin production.	2001 Nov	11592940
Chelerythrine rapidly induces apoptosis through generation of reactive oxygen species in cardiac myocytes.	2001 Oct	11603925
Death by protein kinase C inhibitor: a stressful event.	2001 Oct	11603920
Protein kinase C and changes in manganese superoxide dismutase gene expression in cultured glial cells.	2001 Oct	11553022
Regulation and distribution of MAdCAM-1 in endothelial cells in vitro.	2001 Oct	11546645
Characterization of the signal transduction pathways mediating morphine withdrawal-stimulated c-fos expression in hypothalamic nuclei.	2001 Oct 26	11698063
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro.	2001 Oct 8	11695703
The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes.	2001 Sep	11549349
Mechanism of action of angiotensin II in human isolated subcutaneous resistance arteries.	2001 Sep	11522611
Regulation of ATP-sensitive K(+) channels by protein kinase C in murine colonic myocytes.	2001 Sep	11502563
Induction of osteoblast differentiation indexes by PTHrP in MG-63 cells involves multiple signaling pathways.	2001 Sep	11500304
Protein kinase C regulation of cell spreading in the molluscan Biomphalaria glabrata embryonic (Bge) cell line.	2001 Sep 26	11583819

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 `Sat Dec 16 10:58:47 GMT 2023` Edited by `admin` on `Sat Dec 16 10:58:47 GMT 2023`
Record UNII	65ML87R6OI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHELERYTHRINE HYDROXIDE

Common Name

English

HELLERITRINE HYDROXIDE

Common Name

English

CHELERYTHRINIUM HYDROXIDE

Common Name

English

TODDALINE HYDROXIDE

Common Name

English

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

Systematic Name

English

NSC-76023

Code

English

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

Systematic Name

English

TODDALIN HYDROXIDE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID60963940