3-METHYLCHOLANTHRENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H16
Molecular Weight	268.3517
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C2CCC3=C2C(C=C1)=CC4=C5C=CC=CC5=CC=C34

InChI

InChIKey=PPQNQXQZIWHJRB-UHFFFAOYSA-N

InChI=1S/C21H16/c1-13-6-7-15-12-20-17-5-3-2-4-14(17)8-9-18(20)19-11-10-16(13)21(15)19/h2-9,12H,10-11H2,1H3

HIDE SMILES / InChI

Molecular Formula	C21H16
Molecular Weight	268.3517
Charge	0
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/16489053 | https://www.ncbi.nlm.nih.gov/pubmed/29094188

3-Methylcholanthrene a compound, which can activate both aryl hydrocarbon receptor (AhR) and estrogen receptor alpha. It is used to induce fibrosarcomas and skin carcinomas in laboratory animals. The daily exposure to 3-methylcholanthrene induced changes in both gene expression and epigenomic remodeling, which had led to premature ovarian failure.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aryl hydrocarbon receptor 26 Target ID: P35869 Gene ID: 196.0 Gene Symbol: AHR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14672759	Agonist 2678
Estrogen receptor 75 Target ID: P03372 Gene ID: 2099.0 Gene Symbol: ESR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16489053	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Comparison of the levels of enzymes involved in drug metabolism between transgenic or gene-knockout and the parental mice.	2001	11695553
Monoclonal antibody-directed analysis of benzo[a]pyrene metabolism in rat liver and extrahepatic tissues: effect of propyl and octyl gallate.	2001	11588892
[Effect of L-lysine-alpha-oxidase on skin carcinoma induced by methylcholanthrene in mice].	2001	11550500
Inhibitory effects of thymoquinone against 20-methylcholanthrene-induced fibrosarcoma tumorigenesis.	2001	11531013
Protective effect of Picroliv, the active constituent of Picrorhiza kurroa, against chemical carcinogenesis in mice.	2001	11406836
The suitability of hepatocyte culture models to study various aspects of drug metabolism.	2001	11378681
Regulation of prostaglandin synthesis and cell adhesion by a tryptophan catabolizing enzyme.	2001	11375052
Application of the ethoxyresorufin-O-deethylase (EROD) assay to mixtures of halogenated aromatic compounds.	2001	11339718
Cytochrome P450 1A1 and 4A activities in isolated rat spleen lymphocytes.	2001 Apr	11338675
Monitoring expression of genes involved in drug metabolism and toxicology using DNA microarrays.	2001 Apr 27	11328961
Modification of membrane-toxic effect of Nd-YAG laser by preliminary induction of cytochrome P-450 in bone marrow cells.	2001 Aug	11713574
Oxidative stress induces the expression of the major histocompatibility complex in murine tumor cells.	2001 Aug	11697192
Metabolism of aflatoxin B1 by normal human bronchial epithelial cells.	2001 Aug 10	11497333
Clustering of hepatotoxins based on mechanism of toxicity using gene expression profiles.	2001 Aug 15	11509024
3-Methylcholanthrene increases phorbol 12-myristate 13-acetate-induced respiratory burst activity and intracellular calcium levels in common carp (Cyprinus carpio L) macrophages.	2001 Aug 15	11509021
Immunohistochemical evidence for the expression and induction of paraoxonase in rat liver, kidney, lung and brain tissue. Implications for its physiological role.	2001 Aug 31	11551529
Structure and expression of the Ah receptor repressor gene.	2001 Aug 31	11423533
Identity between the PCPH proto-oncogene and the CD39L4 (ENTPD5) ectonucleoside triphosphate diphosphohydrolase gene.	2001 Dec	11713596
Induction by xenobiotics of phase I and phase II enzyme activities in the human keratinocyte cell line NCTC 2544.	2001 Dec	11698172
Effect of cytochrome P450 1A induction on oxidative damage in rat brain.	2001 Jul	11681726
Characterization of enzymes involved in biotransformation of polycyclic aromatic hydrocarbons in terrestrial isopods.	2001 Jul	11434285
An alternative promoter contributes to tissue- and inducer-specific expression of the rat UDP-glucuronosyltransferase 1A6 gene.	2001 Jul 1	11437649
Expression and induction of cytochrome P450s in rabbit parotid glands.	2001 Jul 15	11389885
Oxidative stress in zebrafish cells: potential utility of transgenic zebrafish as a deployable sentinel for site hazard ranking.	2001 Jul 2	11453295
2,5-Di-tert-butyl-1,4-hydroquinone enhances cell transformation accompanied by an increase in intracellular free calcium ion concentration.	2001 Jul 26	11403923
Measurement of cytochrome P4501A induction in dab (Limanda limanda) and other teleosts with species-specific cDNA probes: isolation and characterisation of dab cDNA and its use in expression studies with beta-naphthoflavone-treated fish.	2001 Jun	11423384
Differential effects of microsomal enzyme-inducing chemicals on the hepatic expression of rat organic anion transporters, OATP1 and OATP2.	2001 Jun	11391536
Unique gene expression patterns in liver and kidney associated with exposure to chemical toxicants.	2001 Jun	11356909
Cytochrome P450 1A1 (CYP1A1) in blood lymphocytes evidence for catalytic activity and mRNA expression.	2001 Jun 15	11459429
p-Nonylphenol acts as a promoter in the BALB/3T3 cell transformation.	2001 Jun 27	11516725
Polycyclic aromatic hydrocarbons as inducers of cytochrome P4501A enzyme activity in the rainbow trout liver cell line, RTL-W1, and in primary cultures of rainbow trout hepatocytes.	2001 Mar	11349866
Density differential responses of embryonic fibroblasts.	2001 May	11513079
Inhibition of chemical carcinogenesis by berberine in rats and mice.	2001 May	11370717
Chemopreventive activity of Withania somnifera in experimentally induced fibrosarcoma tumours in Swiss albino mice.	2001 May	11351360
Growth inhibition of mouse skin tumor by serine protease inhibitor ONO-3403.	2001 May-Jun	11497262
S9 induction by the combined treatment with cyclohexanol and albendazole.	2001 Nov	11682644
N-benzylimidazole for preparation of S9 fraction with multi-induction of metabolizing enzymes in short-term genotoxicity assays.	2001 Nov	11682638
Regulation of rat carboxylesterase expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD): a dose-dependent decrease in mRNA levels but a biphasic change in protein levels and activity.	2001 Nov	11606798
Toxicity of alpidem, a peripheral benzodiazepine receptor ligand, but not zolpidem, in rat hepatocytes: role of mitochondrial permeability transition and metabolic activation.	2001 Nov	11602696
Efficient chromosomal mapping of a methylcholanthrene-induced tumor antigen by CTL immunoselection.	2001 Nov 1	11673526
Activation of HTLV-I long terminal repeat by stress-inducing agents and protection of HTLV-I-infected T-cells from apoptosis by the viral tax protein.	2001 Nov 15	11697893
Induction of rat liver cytochrome P450 isoenzymes CYP 1A and CYP 2B by different fungicides, nitrofurans, and quercetin.	2001 Nov 15	11673071
Digitonin enhances the antitumor effect of cisplatin during isolated lung perfusion.	2001 Oct	11603432
Alterations at the Ink4a locus in transplacentally induced murine lung tumors.	2001 Oct 22	11595130
Application of the PKCYP-test in cases of altered CYP1A2 for multiple CYP systems in rat models of disease.	2001 Sep	11558565
Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5.	2001 Sep	11502733
Gender differences in tumor-induced anorectic feeding pattern in Fischer-344 rats.	2001 Sep 1-15	11564448
Aryl hydrocarbon receptor-mediated suppression of expression of the low-molecular-weight prekininogen gene in mice.	2001 Sep 14	11549291
Morphological transformation of Syrian hamster embryo cells at pH 6.7 by bemitradine, a nongenotoxic carcinogen.	2001 Summer	11690565
Mechanism of p53-dependent apoptosis induced by 3-methylcholanthrene: involvement of p53 phosphorylation and p38 MAPK.	2002 Jan 18	11706017

Sample Use Guides

In Vivo Use Guide

in rats: daily intraperitoneally injected with 0.1 or 1 mg/kg. It induced changes in both gene expression and epigenomic remodeling, which may lead to premature ovarian failure.

Route of Administration: Intraperitoneal

In Vitro Use Guide

It was investigated the proliferation and angiogenesis of human umbilical vascular endothelial cells under the action of 3-methylcholanthrene (3-MC). 3-MC (concentration: 5 nM; 50 nM; 500 nM) suppressed DNA synthesis of human umbilical vascular endothelial cells as determined by [(3)H]thymidine incorporation in a concentration-dependent fashion and arrested cells at the G0/G1 phase of the cell cycle. Cell permeability, adhesion, and tube formation in human umbilical vascular endothelial cells exposed to 3-MC decreased in concentration-dependent manners.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:15:22 UTC 2023` Edited by `admin` on `Fri Dec 15 17:15:22 UTC 2023`
Record UNII	214U33M1RL
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

3-METHYLCHOLANTHRENE

Systematic Name

English

20-METHYLCHOLANTHRENE

Common Name

English

3-METHYLCHOLANTHRENE [MI]

Common Name

English

NSC-21970

Code

English

3-MECA

Common Name

English

1,2-DIHYDRO-3-METHYLBENZ(J)ACEANTHRYLENE

Systematic Name

English

3-METHYLCHOLANTHRENE [HSDB]

Common Name

English

3-MC

Common Name

English

METHYLCHOLANTHRENE, 3-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C761