Details of the Drug

General Information of Drug (ID: DM8E54P)

Drug Name
BUTEIN
Synonyms
butein; 487-52-5; 2',3,4,4'-Tetrahydroxychalcone; 3,4,2',4'-Tetrahydroxychalcone; 2',4',3,4-Tetrahydroxychalcone; UNII-4WVS5M0LGF; EINECS 207-659-5; 4WVS5M0LGF; (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one; CHEMBL128000; CHEBI:3237; (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one; 1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one; ,3,4-Tetrahydroxychalcone; Chalcone, 2',3,4,4'-tetrahydroxy- (7CI,8CI); Acrylophenone, 2',4'-dihydroxy-3-(3,4-dihy
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) 272.25
Logarithm of the Partition Coefficient (xlogp) 2.8
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C15H12O5
IUPAC Name
(E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
Canonical SMILES
C1=CC(=C(C=C1/C=C/C(=O)C2=C(C=C(C=C2)O)O)O)O
InChI
InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+
InChIKey
AYMYWHCQALZEGT-ORCRQEGFSA-N
Cross-matching ID
PubChem CID
5281222
ChEBI ID
CHEBI:3237
CAS Number
487-52-5
TTD ID
D0EW3L

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Angiotensin-converting enzyme (ACE) TTL69WB ACE_HUMAN Inhibitor [1]
Plasmodium Enoyl-ACP reductase (Malaria fabI) TTNX2CS Q965D5_PLAFA Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [3]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [4]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [4]
Matrix metalloproteinase-9 (MMP9) OTB2QDAV MMP9_HUMAN Gene/Protein Processing [5]
Microtubule-associated proteins 1A/1B light chain 3B (MAP1LC3B) OTUYHB84 MLP3B_HUMAN Post-Translational Modifications [4]
Mitogen-activated protein kinase 8 (MAPK8) OTEREYS5 MK08_HUMAN Post-Translational Modifications [4]
NAD-dependent protein deacetylase sirtuin-1 (SIRT1) OTAYZMOY SIR1_HUMAN Gene/Protein Processing [6]
Nuclear factor erythroid 2-related factor 2 (NFE2L2) OT0HENJ5 NF2L2_HUMAN Protein Interaction/Cellular Processes [7]
Nuclear factor NF-kappa-B p105 subunit (NFKB1) OTNRRD8I NFKB1_HUMAN Protein Interaction/Cellular Processes [5]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_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
Angiotensin-converting enzyme (ACE) DTT SLC33A1 2.62E-01 -0.01 -0.06
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives. Bioorg Med Chem Lett. 2010 Mar 15;20(6):1990-3.
2 Green tea catechins potentiate triclosan binding to enoyl-ACP reductase from Plasmodium falciparum (PfENR). J Med Chem. 2007 Feb 22;50(4):765-75.
3 The depletion of securin enhances butein-induced apoptosis and tumor inhibition in human colorectal cancer. Chem Biol Interact. 2014 Sep 5;220:41-50. doi: 10.1016/j.cbi.2014.06.006. Epub 2014 Jun 12.
4 Effects of butein on human osteosarcoma cell proliferation, apoptosis, and autophagy through oxidative stress. Hum Exp Toxicol. 2022 Jan-Dec;41:9603271221074346. doi: 10.1177/09603271221074346.
5 Butein suppresses the expression of nuclear factor-kappa B-mediated matrix metalloproteinase-9 and vascular endothelial growth factor in prostate cancer cells. Toxicol In Vitro. 2010 Oct;24(7):1927-34. doi: 10.1016/j.tiv.2010.08.002. Epub 2010 Aug 7.
6 The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation. Diabetes. 2007 Mar;56(3):767-76. doi: 10.2337/db06-1488.
7 Butein protects human dental pulp cells from hydrogen peroxide-induced oxidative toxicity via Nrf2 pathway-dependent heme oxygenase-1 expressions. Toxicol In Vitro. 2013 Mar;27(2):874-81. doi: 10.1016/j.tiv.2013.01.003. Epub 2013 Jan 11.
8 Stable cellular models of nuclear receptor PXR for high-throughput evaluation of small molecules. Toxicol In Vitro. 2018 Oct;52:222-234.