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=C3C=CC5=CC=CC=C45

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 27 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 2752
Estrogen receptor 72 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 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Mechanism of p53-dependent apoptosis induced by 3-methylcholanthrene: involvement of p53 phosphorylation and p38 MAPK.	2002-01-18	11706017
Identity between the PCPH proto-oncogene and the CD39L4 (ENTPD5) ectonucleoside triphosphate diphosphohydrolase gene.	2001-12	11713596
Induction by xenobiotics of phase I and phase II enzyme activities in the human keratinocyte cell line NCTC 2544.	2001-12	11698172
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.	2001-11-15	11697893
Induction of rat liver cytochrome P450 isoenzymes CYP 1A and CYP 2B by different fungicides, nitrofurans, and quercetin.	2001-11-15	11673071
Efficient chromosomal mapping of a methylcholanthrene-induced tumor antigen by CTL immunoselection.	2001-11-01	11673526
S9 induction by the combined treatment with cyclohexanol and albendazole.	2001-11	11682644
N-benzylimidazole for preparation of S9 fraction with multi-induction of metabolizing enzymes in short-term genotoxicity assays.	2001-11	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.	2001-11	11606798
Toxicity of alpidem, a peripheral benzodiazepine receptor ligand, but not zolpidem, in rat hepatocytes: role of mitochondrial permeability transition and metabolic activation.	2001-11	11602696
Alterations at the Ink4a locus in transplacentally induced murine lung tumors.	2001-10-22	11595130
Digitonin enhances the antitumor effect of cisplatin during isolated lung perfusion.	2001-10	11603432
Gender differences in tumor-induced anorectic feeding pattern in Fischer-344 rats.	2001-09-21	11564448
Aryl hydrocarbon receptor-mediated suppression of expression of the low-molecular-weight prekininogen gene in mice.	2001-09-14	11549291
Application of the PKCYP-test in cases of altered CYP1A2 for multiple CYP systems in rat models of disease.	2001-09	11558565
Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5.	2001-09	11502733
Immunohistochemical evidence for the expression and induction of paraoxonase in rat liver, kidney, lung and brain tissue. Implications for its physiological role.	2001-08-31	11551529
Structure and expression of the Ah receptor repressor gene.	2001-08-31	11423533
Clustering of hepatotoxins based on mechanism of toxicity using gene expression profiles.	2001-08-15	11509024
3-Methylcholanthrene increases phorbol 12-myristate 13-acetate-induced respiratory burst activity and intracellular calcium levels in common carp (Cyprinus carpio L) macrophages.	2001-08-15	11509021
Growth inhibition of mouse skin tumor by serine protease inhibitor ONO-3403.	2001-08-11	11497262
Metabolism of aflatoxin B1 by normal human bronchial epithelial cells.	2001-08-10	11497333
Modification of membrane-toxic effect of Nd-YAG laser by preliminary induction of cytochrome P-450 in bone marrow cells.	2001-08	11713574
Oxidative stress induces the expression of the major histocompatibility complex in murine tumor cells.	2001-08	11697192
2,5-Di-tert-butyl-1,4-hydroquinone enhances cell transformation accompanied by an increase in intracellular free calcium ion concentration.	2001-07-26	11403923
Expression and induction of cytochrome P450s in rabbit parotid glands.	2001-07-15	11389885
Oxidative stress in zebrafish cells: potential utility of transgenic zebrafish as a deployable sentinel for site hazard ranking.	2001-07-02	11453295
An alternative promoter contributes to tissue- and inducer-specific expression of the rat UDP-glucuronosyltransferase 1A6 gene.	2001-07-01	11437649
Effect of cytochrome P450 1A induction on oxidative damage in rat brain.	2001-07	11681726
Characterization of enzymes involved in biotransformation of polycyclic aromatic hydrocarbons in terrestrial isopods.	2001-07	11434285
p-Nonylphenol acts as a promoter in the BALB/3T3 cell transformation.	2001-06-27	11516725
Cytochrome P450 1A1 (CYP1A1) in blood lymphocytes evidence for catalytic activity and mRNA expression.	2001-06-15	11459429
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.	2001-06	11423384
Differential effects of microsomal enzyme-inducing chemicals on the hepatic expression of rat organic anion transporters, OATP1 and OATP2.	2001-06	11391536
Unique gene expression patterns in liver and kidney associated with exposure to chemical toxicants.	2001-06	11356909
Density differential responses of embryonic fibroblasts.	2001-05	11513079
Inhibition of chemical carcinogenesis by berberine in rats and mice.	2001-05	11370717
Chemopreventive activity of Withania somnifera in experimentally induced fibrosarcoma tumours in Swiss albino mice.	2001-05	11351360
Monitoring expression of genes involved in drug metabolism and toxicology using DNA microarrays.	2001-04-27	11328961
Cytochrome P450 1A1 and 4A activities in isolated rat spleen lymphocytes.	2001-04	11338675
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.	2001-03	11349866
Comparison of the levels of enzymes involved in drug metabolism between transgenic or gene-knockout and the parental mice.	2001	11695553
Morphological transformation of Syrian hamster embryo cells at pH 6.7 by bemitradine, a nongenotoxic carcinogen.	2001	11690565
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

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 `Mon Mar 31 18:43:01 GMT 2025` Edited by `admin` on `Mon Mar 31 18:43:01 GMT 2025`
Record UNII	214U33M1RL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-METHYLCHOLANTHRENE

Systematic Name

English

NSC-21970

Preferred Name

English

20-METHYLCHOLANTHRENE

Common Name

English

3-METHYLCHOLANTHRENE [MI]

Common Name

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