Details of the Drug

General Information of Drug (ID: DMES906)

Drug Name
3,7,3',4'-TETRAHYDROXYFLAVONE
Synonyms
Fisetin; 528-48-3; 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one; 5-Desoxyquercetin; Fustel; Cotinin; Viset; 3,3',4',7-Tetrahydroxyflavone; Fisetholz; Superfustel; Fustet; Fietin; Junger fustik; 3,7,3',4'-Tetrahydroxyflavone; Ventin sumach; Zante fustic; Young fustic; Superfustel K; Ungarisches gelbholz; CI Natural Brown 1; Young fustic crystals; Bois bleu de Honqrie; BOIS bleude honqrie; CI 75620; NSC 407010; NSC 656275; 5-Deoxyquercetin; 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one; Natural Brown 1; FISETIN
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) 286.24
Logarithm of the Partition Coefficient (xlogp) 2
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C15H10O6
IUPAC Name
2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one
Canonical SMILES
C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
InChI
InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
InChIKey
XHEFDIBZLJXQHF-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5281614
ChEBI ID
CHEBI:42567
CAS Number
528-48-3
UNII
OO2ABO9578
DrugBank ID
DB07795
TTD ID
D0MF5Y
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cyclin-dependent kinase 6 (CDK6) TTO0FDJ CDK6_HUMAN Inhibitor [1]
Fatty acid synthase (FASN) TT7AOUD FAS_HUMAN Inhibitor [2]
Plasmodium Beta-hydroxyacyl-ACP dehydratase (Malaria FabZ) TTHPFTS Q965D7_PLAFA Inhibitor [2]
Plasmodium Enoyl-ACP reductase (Malaria fabI) TTNX2CS Q965D5_PLAFA Inhibitor [2]
Plasmodium Oxoacyl-[acyl-carrier protein] reductase (Malaria fabG) TTBE4IR Q965D6_PLAFA Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [3]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [4]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [5]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Protein Interaction/Cellular Processes [5]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [4]
BH3-interacting domain death agonist (BID) OTOSHSHU BID_HUMAN Protein Interaction/Cellular Processes [6]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [7]
Calpain-1 catalytic subunit (CAPN1) OTK6OQZR CAN1_HUMAN Gene/Protein Processing [5]
Calpain-2 catalytic subunit (CAPN2) OTIAPE5J CAN2_HUMAN Gene/Protein Processing [5]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [8]
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
Cyclin-dependent kinase 6 (CDK6) DTT CDK6 1.12E-14 -0.67 -1.3
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
2 Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. J Med Chem. 2006 Jun 1;49(11):3345-53.
3 A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice. Cancer Res. 2008 Oct 15;68(20):8555-63. doi: 10.1158/0008-5472.CAN-08-0240.
4 Fisetin activates Hippo pathway and JNK/ERK/AP-1 signaling to inhibit proliferation and induce apoptosis of human osteosarcoma cells via ZAK overexpression. Environ Toxicol. 2019 Aug;34(8):902-911. doi: 10.1002/tox.22761. Epub 2019 May 1.
5 Fisetin-induced apoptosis of human oral cancer SCC-4 cells through reactive oxygen species production, endoplasmic reticulum stress, caspase-, and mitochondria-dependent signaling pathways. Environ Toxicol. 2017 Jun;32(6):1725-1741. doi: 10.1002/tox.22396. Epub 2017 Feb 9.
6 Anticancer activity of a combination of cisplatin and fisetin in embryonal carcinoma cells and xenograft tumors. Mol Cancer Ther. 2011 Feb;10(2):255-68. doi: 10.1158/1535-7163.MCT-10-0606. Epub 2011 Jan 7.
7 Fisetin suppresses migration, invasion and stem-cell-like phenotype of human non-small cell lung carcinoma cells via attenuation of epithelial to mesenchymal transition. Chem Biol Interact. 2019 Apr 25;303:14-21. doi: 10.1016/j.cbi.2019.02.020. Epub 2019 Feb 22.
8 Fisetin induces apoptosis in human cervical cancer HeLa cells through ERK1/2-mediated activation of caspase-8-/caspase-3-dependent pathway. Arch Toxicol. 2012 Feb;86(2):263-73. doi: 10.1007/s00204-011-0754-6. Epub 2011 Oct 1.