Details of the Drug

General Information of Drug (ID: DMGHQ37)

Drug Name

ICARITIN

Synonyms

Icaritin; 118525-40-9; UNII-UFE666UELY; UFE666UELY; CHEMBL498485; 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one; 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one; Icartin; Anhydroicaritin; AC1NSXIV; Icaritin(Anhydroicaritin); MLS006010055; BIDD:ER0021; SCHEMBL4223542; Icaritin, > DTXSID00152154; MolPort-020-006-012; TUUXBSASAQJECY-UHFFFAOYSA-N; HY-N0678; ZINC14762797; BDBM50272527; AKOS015896858; CS-3679; DB12672; NCGC00345813-01; AK168251; SMR004701218

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Phase 2	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

368.4

Logarithm of the Partition Coefficient (xlogp)

4.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C21H20O6
IUPAC Name: 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
Canonical SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=CC=C(C=C3)OC)O)C
InChI: InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
InChIKey: TUUXBSASAQJECY-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5318980
CAS Number: 118525-40-9
DrugBank ID: DB12672
TTD ID: D0L0BX
VARIDT ID: DR00813

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Estrogen receptor (ESR)	TTZAYWL	ESR1_HUMAN	Modulator	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[3]
Cytochrome P450 2C19 (CYP2C19)	OTFMJYYE	CP2CJ_HUMAN	Gene/Protein Processing	[3]
Cytochrome P450 2C9 (CYP2C9)	OTGLBN29	CP2C9_HUMAN	Gene/Protein Processing	[3]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Regulation of Drug Effects	[4]
Cytochrome P450 3A5 (CYP3A5)	OTSXFBXB	CP3A5_HUMAN	Regulation of Drug Effects	[4]
Estrogen receptor (ESR1)	OTKLU61J	ESR1_HUMAN	Gene/Protein Processing	[5]
Estrogen receptor beta (ESR2)	OTXNR2WQ	ESR2_HUMAN	Gene/Protein Processing	[5]
Peroxisome proliferator-activated receptor gamma (PPARG)	OTHMARHO	PPARG_HUMAN	Gene/Protein Processing	[6]
Progesterone receptor (PGR)	OT0FZ3QE	PRGR_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	ClinicalTrials.gov (NCT01972672) The Phase II Study of Icaritin in Patients With Advanced Hepatocellular Carcinoma. U.S. National Institutes of Health.
2	A novel prenylflavone restricts breast cancer cell growth through AhR-mediated destabilization of ER protein.Carcinogenesis.2012 May;33(5):1089-97.
3	Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.
4	Identification of Quinone Methide Intermediate Resulting from Metabolic Activation of Icaritin in Vitro and in Vivo. Chem Res Toxicol. 2019 Jun 17;32(6):969-973. doi: 10.1021/acs.chemrestox.8b00418. Epub 2019 Apr 9.
5	Estrogenic/antiestrogenic activities of a Epimedium koreanum extract and its major components: in vitro and in vivo studies. Food Chem Toxicol. 2012 Aug;50(8):2751-9. doi: 10.1016/j.fct.2012.05.017. Epub 2012 May 18.
6	PPAR mediates the anti-pulmonary fibrosis effect of icaritin. Toxicol Lett. 2021 Oct 10;350:81-90. doi: 10.1016/j.toxlet.2021.06.014. Epub 2021 Jun 18.
7	Estrogenic effects of two derivatives of icariin on human breast cancer MCF-7 cells. Phytomedicine. 2005 Nov;12(10):735-41. doi: 10.1016/j.phymed.2004.10.002.