Details of the Drug

General Information of Drug (ID: DMWY0TN)

Drug Name
LICOAGROCHACONE A
Synonyms
licochalcone a; 58749-22-7; Licochalcone-A; UNII-JTV5467968; 3-Dimethylallyl-4,4'-dihydroxy-6-methoxychalcone; CHEMBL139702; C21H22O4; JTV5467968; (E)-3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one; Licochalcone-A, Synthetic; Q-100677; (E)-3-[5-(1,1-dimethylallyl)-4-hydroxy-2-methoxy-phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one; 2-Propen-1-one, 3-(5-(1,1-dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-, (E)-
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) 338.4
Logarithm of the Partition Coefficient (xlogp) 4.9
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C21H22O4
IUPAC Name
(E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
Canonical SMILES
CC(C)(C=C)C1=C(C=C(C(=C1)/C=C/C(=O)C2=CC=C(C=C2)O)OC)O
InChI
InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+
InChIKey
KAZSKMJFUPEHHW-DHZHZOJOSA-N
Cross-matching ID
PubChem CID
5318998
ChEBI ID
CHEMBL139702
CAS Number
58749-22-7
TTD ID
D08GEN
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP 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
PTPN1 messenger RNA (PTPN1 mRNA) TTELIN2 PTN1_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [2]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [2]
Bcl-2-binding component 3, isoforms 3/4 (BBC3) OTUAXDAY BBC3B_HUMAN Gene/Protein Processing [2]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Gene/Protein Processing [2]
CCN family member 1 (CCN1) OTKJBEMD CCN1_HUMAN Gene/Protein Processing [3]
CCN family member 2 (CCN2) OTC39NSU CCN2_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [2]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [4]
Dual specificity mitogen-activated protein kinase kinase 4 (MAP2K4) OTZPZX11 MP2K4_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [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
PTPN1 messenger RNA (PTPN1 mRNA) DTT PTPN1 9.44E-01 7.21E-03 0.08
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B. Bioorg Med Chem Lett. 2009 Sep 1;19(17):5155-7.
2 Licochalcone A from licorice root, an inhibitor of human hepatoma cell growth via induction of cell apoptosis and cell cycle arrest. Food Chem Toxicol. 2018 Oct;120:407-417. doi: 10.1016/j.fct.2018.07.044. Epub 2018 Jul 25.
3 Licochalcone A inhibits cell growth through the downregulation of the Hippo pathway via PES1 in cholangiocarcinoma cells. Environ Toxicol. 2022 Mar;37(3):564-573. doi: 10.1002/tox.23422. Epub 2021 Nov 30.
4 Inhibition of human cytochrome P450 enzymes by licochalcone A, a naturally occurring constituent of licorice. Toxicol In Vitro. 2015 Oct;29(7):1569-76.
5 Synergistic antimetastatic effect of cotreatment with licochalcone A and sorafenib on human hepatocellular carcinoma cells through the inactivation of MKK4/JNK and uPA expression. Environ Toxicol. 2018 Dec;33(12):1237-1244. doi: 10.1002/tox.22630. Epub 2018 Sep 6.
6 Licochalcone A induces apoptotic cell death via JNK/p38 activation in human nasopharyngeal carcinoma cells. Environ Toxicol. 2019 Jul;34(7):853-860. doi: 10.1002/tox.22753. Epub 2019 Apr 14.