Page last updated: 2024-11-11

licochalcone c

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Description

licochalcone C: has cardioprotective, antioxidant, anti-inflammatory and anti-apoptotic activities; isolated from licorice; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9840805
CHEMBL ID141207
SCHEMBL ID7194029
MeSH IDM000608732

Synonyms (32)

Synonym
LMPK12120423
licochalcone c
(e)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
CHEMBL141207 ,
3-(4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
bdbm50301046
(e)-3-[4-hydroxy-2-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-1-(4-hydroxy-phenyl)-propenone
(2e)-3-(4-hydroxy-2-methoxy-3-(3-methyl-2-butenyl)phenyl)-1-(4-hydroxyphenyl)-2-propen-1-one
2-propen-1-one, 3-(4-hydroxy-2-methoxy-3-(3-methyl-2-butenyl)phenyl)-1-(4-hydroxyphenyl)-, (2e)-
p1h7w3812o ,
licochalcone c [mi]
2-propen-1-one, 3-(4-hydroxy-2-methoxy-3-(3-methyl-2-butenyl)phenyl)-1-(4-hydroxyphenyl)-, (e)-
unii-p1h7w3812o
144506-14-9
SCHEMBL7194029
AC-34243
licochalcone-c
DTXSID40162737
4,4'-dihydroxy-2-methoxy-3-prenylchalcone
AKOS030573587
licochalconec
HY-N0374
CS-0008919
((2e)-3-(4-hydroxy-2-methoxy-3-(3-methyl-2-butenyl) phenyl)-1-(4-hydroxyphenyl) -2-propen-1-one
Q27286010
chalcone base + 2o, 1meo, 1prenyl
MS-25151
EN300-6512984
(2e)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
EN300-6499180
Z2312381236

Research Excerpts

Overview

Licochalcone C (LCC) is a flavonoid compound extracted from Licorice. LCC has a variety of clinical uses including anti-cancer, anti-inflammatory and anti-oxidant effects.

ExcerptReferenceRelevance
"Licochalcone C (LCC) is a flavonoid compound extracted from Licorice, with a variety of clinical uses including anti-cancer, anti-inflammatory and anti-oxidant effects."( Licochalcone C induces cell cycle G1 arrest and apoptosis in human esophageal squamous carcinoma cells by activation of the ROS/MAPK signaling pathway.
Chae, JI; Cho, SS; Choi, JS; Jeon, YJ; Kwak, AW; Lee, MH; Liu, K; Oh, HN; Shim, JH; Yoon, G, 2020
)
2.72

Treatment

Licochalcone C treatment reduced the levels of the anti‑apoptotic mRNAs. Pretreatment with licochalcone C significantly improved the recovery of LVDP and ±dp/dtmax. It also increased the Levels of SOD and GSH/GSSG ratio.

ExcerptReferenceRelevance
"Licochalcone C treatment reduced the levels of the anti‑apoptotic mRNAs (Bcl‑2, Bcl‑w and Bcl‑XL) and increased expression of the pro‑apoptotic mRNAs (Bax and Bim)."( Licochalcone C induces apoptosis via B-cell lymphoma 2 family proteins in T24 cells.
Sun, X; Wang, P; Wang, Y; Yuan, X; Zhao, H; Zheng, Q, 2015
)
2.58
"Pretreatment with licochalcone C significantly improved the recovery of LVDP and ±dp/dtmax, and increased the levels of SOD and GSH/GSSG ratio. "( Role of licochalcone C in cardioprotection against ischemia/reperfusion injury of isolated rat heart via antioxidant, anti-inflammatory, and anti-apoptotic activities.
Han, J; Liu, L; Ren, H; Wang, D; Wang, W; Zheng, Q; Zhou, M, 2015
)
1.19
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 3A4Homo sapiens (human)IC50 (µMol)57.00000.00011.753610.0000AID775571
Cytochrome P450 2D6Homo sapiens (human)IC50 (µMol)57.00000.00002.015110.0000AID775571
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)43.95000.00053.49849.7600AID447165; AID775571
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (52)

Processvia Protein(s)Taxonomy
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2D6Homo sapiens (human)
steroid metabolic processCytochrome P450 2D6Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2D6Homo sapiens (human)
estrogen metabolic processCytochrome P450 2D6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid catabolic processCytochrome P450 2D6Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2D6Homo sapiens (human)
isoquinoline alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2D6Homo sapiens (human)
retinol metabolic processCytochrome P450 2D6Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2D6Homo sapiens (human)
negative regulation of bindingCytochrome P450 2D6Homo sapiens (human)
oxidative demethylationCytochrome P450 2D6Homo sapiens (human)
negative regulation of cellular organofluorine metabolic processCytochrome P450 2D6Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 2D6Homo sapiens (human)
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (34)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
monooxygenase activityCytochrome P450 2D6Homo sapiens (human)
iron ion bindingCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activityCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2D6Homo sapiens (human)
heme bindingCytochrome P450 2D6Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
mitochondrionCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulumCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2D6Homo sapiens (human)
cytoplasmCytochrome P450 2D6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2D6Homo sapiens (human)
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1453619Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production at 10 uM after 24 hrs by Griess reagent based assay relative to control2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.
AID1453625Inhibition of mushroom tyrosinase at 10 uM using L-tyrosine as substrate incubated for 15 mins followed by substrate addition relative to control2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.
AID1453614Growth inhibition of human MCF7 cells at 10 uM after 24 hrs by MTS assay relative to control2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.
AID1453623Inhibition of recombinant human PTP1B using p-nitrophenyl phosphate as substrate at 10 uM after 30 mins relative to control2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.
AID1061200Antiinflammatory activity in RBL2H3 cells assessed as inhibition of degranulation2014Bioorganic & medicinal chemistry letters, Jan-01, Volume: 24, Issue:1
Synthesis of licochalcone analogues with increased anti-inflammatory activity.
AID447165Inhibition of recombinant human PTP1B assessed as hydrolysis of p-nitrophenyl phosphate after 30 mins2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B.
AID1453615Growth inhibition of human SW480 cells at 10 uM after 24 hrs by MTS assay relative to control2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.
AID1453616Growth inhibition of human HepG2 cells at 10 uM after 24 hrs by MTS assay relative to control2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.
AID1453621Inhibition of LPS-induced NF-kappaB transcription (unknown origin) expressed in human SW480 cells at 10 uM by luciferase reporter gene assay2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata.
AID775571Inhibition of PTP1B (unknown origin) using p-nitrophenyl phosphate as substrate2013Bioorganic & medicinal chemistry letters, Nov-01, Volume: 23, Issue:21
Evaluation of licorice flavonoids as protein tyrosine phosphatase 1B inhibitors.
AID1463920Activation of Nrf2 (unknown origin) expressed in human HepG2 cells at 10 uM incubated for 6 hrs by ARE-driven luciferase reporter gene assay relative to untreated control2017Bioorganic & medicinal chemistry, 10-15, Volume: 25, Issue:20
Nrf2 activators from Glycyrrhiza inflata and their hepatoprotective activities against CCl
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (16.67)29.6817
2010's8 (66.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.22

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.22 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index5.70 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (18.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]