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]
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) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
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
UNII
UFE666UELY
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]

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]
Molecular Interaction Atlas (MIA) 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.