Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMG0PHU)

Drug Name

CYNAROPICRIN Drug Info

Synonyms

Cynaropicrin; aguerin; 35730-78-0; CHEMBL374146; CHEBI:4038; UNII-M9233789I9; M9233789I9; [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate; AC1Q69JD; AC1L3O6W; SCHEMBL1711811; MEGxp0_001095; ACon1_000045; MolPort-001-741-258; ZINC4098049; HY-N2350; BDBM50194430; AKOS032971358; MCULE-5051144608; CS-8041; NCGC00168845-01; NCGC00168845-02; 2-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(m

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Cross-matching ID

PubChem CID: 119093
ChEBI ID: CHEBI:4038
CAS Number: CAS 35730-78-0
TTD Drug ID: DMG0PHU

Molecule-Related Drug Atlas

Molecule Type:

DTT

DOT

Drug Status:

Approved Drug(s)

Investigative Drug(s)

Download the Complete Related Drug List

Drug(s) Targeting Bacterial UDP-N-acetylglucosamine carboxyvinyltransferase (Bact murA)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Fosfomycin	DMVGPMX	Bacterial infection	1A00-1C4Z	Approved	[3]
Uridine-Diphosphate-N-Acetylglucosamine	DMEQSTP	Discovery agent	N.A.	Investigative	[4]
RWJ-3981	DMBVLCQ	Gram-positive bacterial infection	1B74-1G40	Investigative	[5]
RWJ-140998	DMP7SI9	Gram-positive bacterial infection	1B74-1G40	Investigative	[5]
Aminomethylcyclohexane	DMNX9FC	Discovery agent	N.A.	Investigative	[6]
EUPATORIOPICRIN	DM068CY	Discovery agent	N.A.	Investigative	[1]
CNICIN	DMEVM0J	Discovery agent	N.A.	Investigative	[1]
L-Iso-Aspartate	DM26AB4	Discovery agent	N.A.	Investigative	[6]
Cyclohexylammonium Ion	DMYQH2N	Discovery agent	N.A.	Investigative	[6]
------------------------------------------------------------------------------------


⏷ Show the Full List of 9 Drug(s)

Drug(s) Affected By Cytochrome P450 1A1 (CYP1A1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Amodiaquine	DME4RA8	Malaria	1F40-1F45	Approved	[7]
Riluzole	DMECBWN	Amyotrophic lateral sclerosis	8B60.0	Approved	[8]
Flutamide	DMK0O7U	Prostate cancer	2C82.0	Approved	[9]
Menadione	DMSJDTY	Vitamin K deficiency	5B59	Approved	[10]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[11]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[12]
Ethacrynic acid	DM60QMR	Edema	MG29	Approved	[13]
Marinol	DM70IK5	Anorexia nervosa cachexia	6B80	Approved	[14]
Ethinyl Estradiol	DMODJ40	Acne vulgaris	ED80	Approved	[15]
Clofibrate	DMPC1J7	Dysbetalipoproteinemia	5C80.2	Approved	[16]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Affected By NAD(P)H dehydrogenase 1 (NQO1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[17]
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[18]
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[19]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[20]
TECFIDERA	DM2OVDT	Multiple sclerosis	8A40	Approved	[21]
Sulindac	DM2QHZU	Acute myelogenous leukaemia	2A41	Approved	[22]
Simvastatin	DM30SGU	Arteriosclerosis	BD40	Approved	[23]
Lapatinib	DM3BH1Y	Breast cancer	2C60-2C65	Approved	[24]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[25]
Rofecoxib	DM3P5DA	Osteoarthritis	FA00-FA05	Approved	[26]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Affected By Aryl hydrocarbon receptor (AHR)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Fulvestrant	DM0YZC6	Breast cancer	2C60-2C65	Approved	[27]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[28]
Citalopram	DM2G9AE	Acute coronary syndrome	BA41	Approved	[29]
Colchicine	DM2POTE	Acute gout flare	FA25.0	Approved	[30]
Sulindac	DM2QHZU	Acute myelogenous leukaemia	2A41	Approved	[31]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[32]
Omeprazole	DM471KJ	Cystic fibrosis	CA25	Approved	[33]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[34]
Rifampicin	DM5DSFZ	Non-insulin dependent diabetes	5A11	Approved	[35]
Aspirin	DM672AH	Acute coronary syndrome	BA41	Approved	[36]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Affected By Nuclear factor erythroid 2-related factor 2 (NFE2L2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[37]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[38]
Sertraline	DM0FB1J	Coronary heart disease	BA80.Z	Approved	[39]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[20]
Selenium	DM25CGV	N. A.	N. A.	Approved	[40]
TECFIDERA	DM2OVDT	Multiple sclerosis	8A40	Approved	[41]
Simvastatin	DM30SGU	Arteriosclerosis	BD40	Approved	[23]
Lapatinib	DM3BH1Y	Breast cancer	2C60-2C65	Approved	[24]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[42]
Furazolidone	DM3P6V7	Diarrhea	ME05.1	Approved	[43]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Download the Complete Interaction Atlas for Visualization in Cytoscape

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial UDP-N-acetylglucosamine carboxyvinyltransferase (Bact murA)	TTICX3S	MURA_ECOLI	Inhibitor	[1]

------------------------------------------------------------------------------------

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aryl hydrocarbon receptor (AHR)	OTFE4EYE	AHR_HUMAN	Protein Interaction/Cellular Processes	[2]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[2]
NAD(P)H dehydrogenase 1 (NQO1)	OTZGGIVK	NQO1_HUMAN	Gene/Protein Processing	[2]
Nuclear factor erythroid 2-related factor 2 (NFE2L2)	OT0HENJ5	NF2L2_HUMAN	Gene/Protein Processing	[2]

------------------------------------------------------------------------------------

References

1	Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5605-9.
2	Cynaropicrin attenuates UVB-induced oxidative stress via the AhR-Nrf2-Nqo1 pathway. Toxicol Lett. 2015 Apr 16;234(2):74-80.
3	Evidence that the fosfomycin target Cys115 in UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) is essential for product release. J Biol Chem. 2005 Feb 4;280(5):3757-63.
4	DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res. 2011 Jan;39(Database issue):D1035-41.
5	Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
6	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
7	Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42.
8	Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
9	Anti-androgenic effect of 6-formylindolo[3,2-b]carbazole (FICZ) in LNCaP cells is mediated by the aryl hydrocarbon-androgen receptors cross-talk. Steroids. 2020 Jan;153:108508. doi: 10.1016/j.steroids.2019.108508. Epub 2019 Oct 3.
10	Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. Arch Toxicol. 2008 Dec;82(12):909-21.
11	Effect of CYP1A1 gene polymorphisms on estrogen metabolism and bone density. J Bone Miner Res. 2005 Feb;20(2):232-9. doi: 10.1359/JBMR.041110. Epub 2004 Nov 16.
12	Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
13	Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res. 1999 Feb 1;59(3):607-14.
14	Gene expression changes in human small airway epithelial cells exposed to Delta9-tetrahydrocannabinol. Toxicol Lett. 2005 Aug 14;158(2):95-107.
15	The metallohormone cadmium modulates AhR-associated gene expression in the small intestine of rats similar to ethinyl-estradiol. Arch Toxicol. 2013 Apr;87(4):633-43.
16	Evidence for a new human CYP1A1 regulation pathway involving PPAR-alpha and 2 PPRE sites. Gastroenterology. 2004 Nov;127(5):1436-45.
17	Transcriptomics hit the target: monitoring of ligand-activated and stress response pathways for chemical testing. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):7-18.
18	Functional cardiotoxicity assessment of cosmetic compounds using human-induced pluripotent stem cell-derived cardiomyocytes. Arch Toxicol. 2018 Jan;92(1):371-381.
19	Cannabidiol induces antioxidant pathways in keratinocytes by targeting BACH1. Redox Biol. 2020 Jan;28:101321. doi: 10.1016/j.redox.2019.101321. Epub 2019 Sep 5.
20	Gypenosides protect retinal pigment epithelium cells from oxidative stress. Food Chem Toxicol. 2018 Feb;112:76-85.
21	Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells. Anticancer Drugs. 2005 Feb;16(2):167-74.
22	Growth-suppressive effect of non-steroidal anti-inflammatory drugs on 11 colon-cancer cell lines and fluorescence differential display of genes whose expression is influenced by sulindac. Int J Cancer. 2000 Dec 15;88(6):873-80. doi: 10.1002/1097-0215(20001215)88:6<873::aid-ijc6>3.0.co;2-b.
23	Simvastatin protects dopaminergic neurons against MPP+-induced oxidative stress and regulates the endogenous anti-oxidant system through ERK. Cell Physiol Biochem. 2018;51(4):1957-1968.
24	P450 3A-catalyzed O-dealkylation of lapatinib induces mitochondrial stress and activates Nrf2. Chem Res Toxicol. 2016 May 16;29(5):784-96.
25	Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin. Toxicol Lett. 2001 Feb 3;119(1):49-57.
26	Rofecoxib modulates multiple gene expression pathways in a clinical model of acute inflammatory pain. Pain. 2007 Mar;128(1-2):136-47.
27	Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
28	Oxidative stress modulates expression of immune checkpoint genes via activation of AhR signaling. Toxicol Appl Pharmacol. 2022 Dec 15;457:116314. doi: 10.1016/j.taap.2022.116314. Epub 2022 Nov 9.
29	Profiling of enantiopure drugs towards aryl hydrocarbon (AhR), glucocorticoid (GR) and pregnane X (PXR) receptors in human reporter cell lines. Chem Biol Interact. 2014 Feb 5;208:64-76. doi: 10.1016/j.cbi.2013.11.018. Epub 2013 Dec 6.
30	Involvement of cytoskeleton in AhR-dependent CYP1A1 expression. Curr Drug Metab. 2006 Apr;7(3):301-13. doi: 10.2174/138920006776359310.
31	Sulindac and its metabolites induce carcinogen metabolizing enzymes in human colon cancer cells. Int J Cancer. 2008 Mar 1;122(5):990-8.
32	Quercetin, quercetin glycosides and taxifolin differ in their ability to induce AhR activation and CYP1A1 expression in HepG2 cells. Phytother Res. 2012 Nov;26(11):1746-52.
33	Omeprazole inhibits pancreatic cancer cell invasion through a nongenomic aryl hydrocarbon receptor pathway. Chem Res Toxicol. 2015 May 18;28(5):907-18.
34	Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
35	Expression and inducibility of cytochrome P450s (CYP1A1, 2B6, 2E1, 3A4) in human cord blood CD34(+) stem cell-derived differentiating neuronal cells. Toxicol Sci. 2012 Oct;129(2):392-410.
36	Induction of paraoxonase 1 and apolipoprotein A-I gene expression by aspirin. J Lipid Res. 2008 Oct;49(10):2142-8.
37	Gingival Stromal Cells as an In Vitro Model: Cannabidiol Modulates Genes Linked With Amyotrophic Lateral Sclerosis. J Cell Biochem. 2017 Apr;118(4):819-828. doi: 10.1002/jcb.25757. Epub 2016 Nov 28.
38	Protective role of HO-1 for alcohol-dependent liver damage. Dig Dis. 2010;28(6):792-8. doi: 10.1159/000324287. Epub 2011 Apr 27.
39	Sertraline induces endoplasmic reticulum stress in hepatic cells. Toxicology. 2014 Aug 1;322:78-88. doi: 10.1016/j.tox.2014.05.007. Epub 2014 May 24.
40	Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
41	Distinct Nrf2 Signaling Mechanisms of Fumaric Acid Esters and Their Role in Neuroprotection against 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine-Induced Experimental Parkinson's-Like Disease. J Neurosci. 2016 Jun 8;36(23):6332-51. doi: 10.1523/JNEUROSCI.0426-16.2016.
42	Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
43	P21(Waf1/Cip1) plays a critical role in furazolidone-induced apoptosis in HepG2 cells through influencing the caspase-3 activation and ROS generation. Food Chem Toxicol. 2016 Feb;88:1-12. doi: 10.1016/j.fct.2015.12.004. Epub 2015 Dec 11.