Details of the Drug

General Information of Drug (ID: DMM10TG)

Drug Name
Cirsimarin
Synonyms
Cirsimarin; Cirsitakaoside; 13020-19-4; CHEMBL517637; 2-(4-(beta-D-Glucopyranosyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one, 2-(4-(beta-D-glucopyranosyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-; AC1L4LVL; AC1Q6CLV; SCHEMBL2016369; MolPort-019-937-034; BDBM50250467; ZINC31459932; MCULE-1339456605; 4-(5-hydroxy-6,7-dimethoxy-4-oxo-4h-chromen-2-yl)phenyl; LS-39681
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 476.4
Logarithm of the Partition Coefficient (xlogp) 1.2
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 11
Chemical Identifiers
Formula
C23H24O11
IUPAC Name
5-hydroxy-6,7-dimethoxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Canonical SMILES
COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)OC
InChI
InChI=1S/C23H24O11/c1-30-15-8-14-17(19(27)22(15)31-2)12(25)7-13(33-14)10-3-5-11(6-4-10)32-23-21(29)20(28)18(26)16(9-24)34-23/h3-8,16,18,20-21,23-24,26-29H,9H2,1-2H3/t16-,18-,20+,21-,23-/m1/s1
InChIKey
RETJLKUBHXTIGH-FZFRBNDOSA-N
Cross-matching ID
PubChem CID
159460
CAS Number
13020-19-4
TTD ID
D0ZO1R

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [2]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [2]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [2]
C-C chemokine receptor type 5 (CCR5) OTP5FMZ4 CCR5_HUMAN Gene/Protein Processing [2]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [2]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [2]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [2]
Cyclin-A2 (CCNA2) OTPHHYZJ CCNA2_HUMAN Gene/Protein Processing [2]
Cyclin-dependent kinase 2 (CDK2) OTB5DYYZ CDK2_HUMAN Gene/Protein Processing [2]
Cyclin-dependent kinase 4 (CDK4) OT7EP05T CDK4_HUMAN Gene/Protein Processing [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Adenosine-1 active ligands: cirsimarin, a flavone glycoside from Microtea debilis. J Nat Prod. 1997 Jun;60(6):638-41.
2 Flavone cirsimarin impairs cell proliferation, migration, and invasion in MCF-7 cells grown in 2D and 3D models. Toxicol In Vitro. 2022 Sep;83:105416. doi: 10.1016/j.tiv.2022.105416. Epub 2022 Jun 13.