Details of the Drug

General Information of Drug (ID: DMGCF51)

Drug Name
Wogonin
Synonyms
Wogonin; 632-85-9; 5,7-Dihydroxy-8-methoxyflavone; Vogonin; Norwogonin 8-methyl ether; UNII-POK93PO28W; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-methoxy-2-phenyl-; BRN 0287152; POK93PO28W; 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one; CHEMBL16171; FLAVONE, 5,7-DIHYDROXY-8-METHOXY-; CHEBI:10043; XLTFNNCXVBYBSX-UHFFFAOYSA-N; 5,7-dihydroxy-8-methoxy-2-phenylchromen-4-one; 5,7-Dihydroxy-8-methoxy-2-phenyl-chromen-4-one; ST077088; Q-100730; 5,7-dihydroxy-8-methoxy-2-phenyl-4H-1-benzopyran-4-one
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): 0 Molecular Weight (mw) 284.26
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C16H12O5
IUPAC Name
5,7-dihydroxy-8-methoxy-2-phenylchromen-4-one
Canonical SMILES
COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O
InChI
InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
InChIKey
XLTFNNCXVBYBSX-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5281703
ChEBI ID
CHEMBL16171
CAS Number
632-85-9
TTD ID
D00MXS
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [1]
Xanthine dehydrogenase/oxidase (XDH) TT7RJY8 XDH_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 2A (CDKN2A) OTN0ZWAE CDN2A_HUMAN Gene/Protein Processing [4]
Glial fibrillary acidic protein (GFAP) OTQ01ZAS GFAP_HUMAN Gene/Protein Processing [3]
Histone H2AX (H2AX) OT18UX57 H2AX_HUMAN Gene/Protein Processing [4]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [4]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [5]
Organic anion transporter 3 (SLC22A8) OT8BY933 S22A8_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 7.93E-04 -0.29 -0.34
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Inhibitory activity of prostaglandin E2 production by the synthetic 2'-hydroxychalcone analogues: Synthesis and SAR study. Bioorg Med Chem Lett. 2009 Mar 15;19(6):1650-3.
2 Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod. 1988 Mar-Apr;51(2):345-8.
3 GSK3/-catenin signaling is correlated with the differentiation of glioma cells induced by wogonin. Toxicol Lett. 2013 Oct 24;222(2):212-23. doi: 10.1016/j.toxlet.2013.07.013. Epub 2013 Jul 19.
4 Wogonin induces cellular senescence in breast cancer via suppressing TXNRD2 expression. Arch Toxicol. 2020 Oct;94(10):3433-3447. doi: 10.1007/s00204-020-02842-y. Epub 2020 Jul 15.
5 Inhibitory effects of wogonin on the invasion of human breast carcinoma cells by downregulating the expression and activity of matrix metalloproteinase-9. Toxicology. 2011 Apr 11;282(3):122-8. doi: 10.1016/j.tox.2011.01.018. Epub 2011 Feb 2.
6 Potent Inhibitors of Organic Anion Transporters 1 and 3 From Natural Compounds and Their Protective Effect on Aristolochic Acid Nephropathy. Toxicol Sci. 2020 Jun 1;175(2):279-291. doi: 10.1093/toxsci/kfaa033.