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
• #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: CHEBI:10043
  CAS Number: 632-85-9
  TTD ID: D00MXS

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
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[3]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[3]
Arylamine N-acetyltransferase 1 (NAT1)	OTCCNQ3H	ARY1_HUMAN	Gene/Protein Processing	[4]
Beta-galactosidase (GLB1)	OTB0TKAG	BGAL_HUMAN	Gene/Protein Processing	[5]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[3]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[6]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[7]
Cyclin-A2 (CCNA2)	OTPHHYZJ	CCNA2_HUMAN	Gene/Protein Processing	[7]
Cyclin-dependent kinase 2 (CDK2)	OTB5DYYZ	CDK2_HUMAN	Gene/Protein Processing	[6]
Cyclin-dependent kinase 4 (CDK4)	OT7EP05T	CDK4_HUMAN	Gene/Protein Processing	[6]

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

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] Wogonin potentiates the antitumor effects of low dose 5-fluorouracil against gastric cancer through induction of apoptosis by down-regulation of NF-kappaB and regulation of its metabolism. Toxicol Lett. 2010 Sep 1;197(3):201-10.
• [4] Wogonin inhibits N-acetyltransferase activity and gene expression in human leukemia HL-60 cells. Anticancer Res. 2005 Jan-Feb;25(1A):127-32.
• [5] 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.
• [6] 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.
• [7] The ethanol extract of Scutellaria baicalensis and the active compounds induce cell cycle arrest and apoptosis including upregulation of p53 and Bax in human lung cancer cells. Toxicol Appl Pharmacol. 2011 Aug 1;254(3):221-8. doi: 10.1016/j.taap.2011.03.016. Epub 2011 Mar 30.