Natural Product (NP) Details

General Information of the NP (ID: NP6984)
Name
Isoliquiritigenin
Synonyms
2',4,4'-Trihydroxychalcone; 4,2',4'-Trihydroxychalcone; (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one; 6'-deoxychalcone; 2',4',4-Trihydroxychalcone; isoliquirtigenin; UNII-B9CTI9GB8F; C15H12O4; Chalcone, 2',4,4'-trihydroxy-; MFCD00075907; B9CTI9GB8F; 42'4'-trihydroxychalcone; 1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one; (2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one; 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-; Acrylophenone, 2',4'-dihydroxy-3-(p-hydroxyphenyl)-; CHEMBL129795; 13745-20-5; 1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one; CHEBI:310312; (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one; trans-2',4,4'-trihydroxychalcone; 2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-; (E)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenone; (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propene-1-one; GU 17; GU-17; SMR000112969; CCRIS 7676; SR-01000075499; EINECS 237-316-5; BRN 1914295; GU17; iso-Liquiritigenin; Isoliquiritigenin/; ILTG; ISLQ; PubChem21917; Isoliquiritigenin, powder; Spectrum5_000612; (2E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one; 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (E)-; Lopac0_000681; BSPBio_003411; 1-08-00-00707 (Beilstein Handbook Reference); MLS000438943; MLS002207240; MLS006010045; BIDD:ER0235; SCHEMBL161168; SPECTRUM1504200; cid_638278; MEGxp0_001326; 2',4,4'-Trihydroxy-Chalcone; DTXSID2022466; 2'',4'',4-trihydroxychalcone; 2'',4,4''-trihydroxychalcone; ACon1_000047; CHEBI:94010; BCPP000201; HMS2233H18; HMS3262I03; 2,4''-dihydroxy-4-hydroxychalcone; BCP02312; HY-N0102; ZINC3869608; Tox21_500681; ABP000708; BDBM50042944; CCG-40334; CI0036; CMLD3_000056; LMPK12120096; s2404; SBB066136; 2',4,4'-Trihydroxychalcone, 97%; Isoliquiritigenin, analytical standard; AKOS001590146; BCP9000795; CS-1745; DB03285; KS-5256; LP00681; MCULE-1557671934; SDCCGMLS-0066751.P001; SDCCGSBI-0050660.P004; NCGC00090504-01; NCGC00090504-02; NCGC00090504-03; NCGC00090504-04; NCGC00090504-05; NCGC00090504-06; NCGC00090504-07; NCGC00090504-08; NCGC00090504-24; NCGC00261366-01; O271; ST081356; AB0000350; EU-0100681; I0822; N1288; SW219658-1; C08650; I 3766; M-1539; 961I295; A845551; NCGC00090504-04!2',4,4'-Trihydroxychalcone; 2',4'-Dihydroxy-3-(p-hydroxyphenyl)-Acrylophenone; Q-100904; Q3155537; SR-01000075499-1; SR-01000075499-5; BRD-K33583600-001-03-9; BRD-K33583600-001-04-7; 1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenone; 1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-prop-2-en-1-one; (E)-1-[2,4-bis(oxidanyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
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Species Origin Cicer arietinum ...     Click to Show/Hide
Cicer arietinum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Cicer
Species: Cicer arietinum
Robinia pseudoacacia
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Robinia
Species: Robinia pseudoacacia
Glycyrrhiza glabra
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Glycyrrhiza
Species: Glycyrrhiza glabra
Dracaena draco
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asparagales
Family: Asparagaceae
Genus: Dracaena
Species: Dracaena draco
Sophora tomentosa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Sophora
Species: Sophora tomentosa
Dalbergia sericea
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Dalbergia
Species: Dalbergia sericea
Allium ascalonicum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asparagales
Family: Amaryllidaceae
Genus: Allium
Species: Allium ascalonicum
Disease Ovarian cancer [ICD-11: 2C73] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.839
 
MDCK Permeability
 -4.798
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 -0.344
 
PPB
 96.1%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 +++
CYP1A2 substrate
 - -
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 +++
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 +++
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 - -
 
Excretion
CLplasma
 5.761
 
T1/2
 1.376
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 ++
 
Respiratory
 +
 
Human Hepatotoxicity
 -
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 - -
 
Drug-induced Neurotoxicity
 +
 
Hematotoxicity
 - - -
 
Genotoxicity
 ++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H12O4
PubChem CID
638278
Canonical SMILES
C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O
InChI
1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
InChIKey
DXDRHHKMWQZJHT-FPYGCLRLSA-N
CAS Number
CAS 961-29-5
Herb ID
HBIN030896
ETMC ID
2368
SymMap ID
SMIT00122
TCMSP ID
MOL001789
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Docosahexaenoic acid      Hyper-lipoproteinaemia     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Up-regulation Cytochrome c release
Up-regulation ROS generation
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Isoliquiritigenin in combination with docosahexaenoic acid has synergistic anticancer effect on human colorectal cancer cells through ROS-mediated regulation of the JNK and cytochrome c release.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model The CT-26 mouse colon cancer cells (2*106 cells in 0.1 mL PBS) cultured in DMEM with 10% FBS were subcutaneously injected into the right flanks of the BALB/c male mice.
                    Experimental
                    Result(s)		 Isoliquiritigenin inhibits tumor growth and protects the kidney and liver against chemotherapy-induced toxicity in a mouse xenograft model of colon carcinoma.
    γ. A List of Drug(s) Whose Resistance can be Reversed by This NP
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression TRAIL-R2  Molecule Info 
Pathway MAP
                    In-vitro Model HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Isoliquiritigenin has the potential to overcome resistance to TRAIL in cancer cells and its chemopreventive effects may depend on TRAIL function.
Target and Pathway
Target(s) Nuclear factor erythroid 2-related factor 2 (Nrf2)  Molecule Info  [5]
Prostaglandin G/H synthase 2 (COX-2)  Molecule Info  [6]
Proto-oncogene c-Src (SRC)  Molecule Info  [7]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Aspirin triggered resolvin D biosynthesis
3 C20 prostanoid biosynthesis
4 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Protein processing in endoplasmic reticulum Click to Show/Hide
2 ErbB signaling pathway
3 Rap1 signaling pathway
4 Chemokine signaling pathway
5 Endocytosis
6 VEGF signaling pathway
7 Focal adhesion
8 Adherens junction
9 Tight junction
10 Gap junction
11 Platelet activation
12 GABAergic synapse
13 Inflammatory mediator regulation of TRP channels
14 Regulation of actin cytoskeleton
15 GnRH signaling pathway
16 Estrogen signaling pathway
17 Prolactin signaling pathway
18 Thyroid hormone signaling pathway
19 Oxytocin signaling pathway
20 Bacterial invasion of epithelial cells
21 Epithelial cell signaling in Helicobacter pylori infection
22 Shigellosis
23 Tuberculosis
24 Hepatitis B
25 Viral carcinogenesis
26 Proteoglycans in cancer
27 Arachidonic acid metabolism
28 Metabolic pathways
29 NF-kappa B signaling pathway
30 TNF signaling pathway
31 Retrograde endocannabinoid signaling
32 Serotonergic synapse
33 Ovarian steroidogenesis
34 Regulation of lipolysis in adipocytes
35 Leishmaniasis
36 Pathways in cancer
37 Chemical carcinogenesis
38 MicroRNAs in cancer
39 Small cell lung cancer
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
2 IL2 Signaling Pathway
3 IL1 Signaling Pathway
4 TSH Signaling Pathway
5 IL4 Signaling Pathway
6 TGF_beta_Receptor Signaling Pathway
Panther Pathway Angiogenesis Click to Show/Hide
2 Cadherin signaling pathway
3 Integrin signalling pathway
4 Parkinson disease
5 CCKR signaling map ST
6 Endothelin signaling pathway
7 Inflammation mediated by chemokine and cytokine signaling pathway
8 Toll receptor signaling pathway
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
Pathway Interaction Database Endothelins Click to Show/Hide
2 Signaling events mediated by PRL
3 LPA receptor mediated events
4 Atypical NF-kappaB pathway
5 Glypican 1 network
6 Plasma membrane estrogen receptor signaling
7 Signaling events mediated by Hepatocyte Growth Factor Receptor (c-Met)
8 Signaling events mediated by PTP1B
9 S1P3 pathway
10 EPHB forward signaling
11 Nectin adhesion pathway
12 Regulation of p38-alpha and p38-beta
13 CDC42 signaling events
14 Signaling events regulated by Ret tyrosine kinase
15 Arf6 signaling events
16 Signaling events mediated by TCPTP
17 FAS (CD95) signaling pathway
18 Thromboxane A2 receptor signaling
19 Netrin-mediated signaling events
20 Alpha9 beta1 integrin signaling events
21 CXCR4-mediated signaling events
22 EGF receptor (ErbB1) signaling pathway
23 Class I PI3K signaling events
24 Posttranslational regulation of adherens junction stability and dissassembly
25 Regulation of Androgen receptor activity
26 E-cadherin signaling in the nascent adherens junction
27 amb2 Integrin signaling
28 Integrins in angiogenesis
29 ErbB1 downstream signaling
30 Urokinase-type plasminogen activator (uPA) and uPAR-mediated signaling
31 ErbB2/ErbB3 signaling events
32 EPHA forward signaling
33 E-cadherin signaling in keratinocytes
34 PDGFR-beta signaling pathway
35 Nongenotropic Androgen signaling
36 Internalization of ErbB1
37 CXCR3-mediated signaling events
38 Signaling events mediated by VEGFR1 and VEGFR2
39 Syndecan-2-mediated signaling events
40 Class I PI3K signaling events mediated by Akt
41 Syndecan-3-mediated signaling events
42 Ephrin B reverse signaling
43 Trk receptor signaling mediated by PI3K and PLC-gamma
44 EPHA2 forward signaling
45 Alpha-synuclein signaling
46 FGF signaling pathway
47 Alpha4 beta1 integrin signaling events
48 Signaling events mediated by focal adhesion kinase
49 Calcineurin-regulated NFAT-dependent transcription in lymphocytes
50 S1P1 pathway
51 C-MYB transcription factor network
52 Signaling mediated by p38-alpha and p38-beta
53 Calcium signaling in the CD4+ TCR pathway
WikiPathways Oxidative Stress Click to Show/Hide
2 Transcriptional activation by NRF2
3 NRF2 pathway
4 Nuclear Receptors Meta-Pathway
5 Aryl Hydrocarbon Receptor Pathway
6 Mesodermal Commitment Pathway
7 Aryl Hydrocarbon Receptor
8 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
9 Arylhydrocarbon receptor (AhR) signaling pathway
10 ErbB Signaling Pathway
11 Senescence and Autophagy in Cancer
12 Notch Signaling Pathway
13 EPO Receptor Signaling
14 EGF/EGFR Signaling Pathway
15 TGF beta Signaling Pathway
16 Signaling of Hepatocyte Growth Factor Receptor
17 Kit receptor signaling pathway
18 Pregnane X Receptor pathway
19 IL-3 Signaling Pathway
20 Nanoparticle-mediated activation of receptor signaling
21 Polycystic Kidney Disease Pathway
22 Alpha 6 Beta 4 signaling pathway
23 BDNF signaling pathway
24 Integrated Pancreatic Cancer Pathway
25 Oncostatin M Signaling Pathway
26 Interleukin-11 Signaling Pathway
27 AGE/RAGE pathway
28 Signaling Pathways in Glioblastoma
29 TSLP Signaling Pathway
30 Regulation of Microtubule Cytoskeleton
31 FSH signaling pathway
32 Leptin signaling pathway
33 RANKL/RANK Signaling Pathway
34 Integrin-mediated Cell Adhesion
35 Angiogenesis
36 Androgen receptor signaling pathway
37 Prostaglandin Synthesis and Regulation
38 Arachidonic acid metabolism
39 Spinal Cord Injury
40 Eicosanoid Synthesis
41 Selenium Micronutrient Network
References
Reference 1 Isoliquiritigenin Inhibits Ovarian Cancer Metastasis by Reversing Epithelial-to-Mesenchymal Transition. Molecules. 2019 Oct 16;24(20):3725.
Reference 2 Synergistic anticancer effect of docosahexaenoic acid and isoliquiritigenin on human colorectal cancer cells through ROS-mediated regulation of the JNK and cytochrome c release. Mol Biol Rep. 2021 Feb;48(2):1171-1180.
Reference 3 Isoliquiritigenin inhibits tumor growth and protects the kidney and liver against chemotherapy-induced toxicity in a mouse xenograft model of colon carcinoma. J Pharmacol Sci. 2008 Mar;106(3):444-51.
Reference 4 Combination of isoliquiritigenin and tumor necrosis factor-related apoptosis-inducing ligand induces apoptosis in colon cancer HT29 cells. Environ Health Prev Med. 2008 Sep;13(5):281-7.
Reference 5 Isoliquiritigenin alleviates early brain injury after experimental intracerebral hemorrhage via suppressing ROS- and/or NF-KappaB-mediated NLRP3 inflammasome activation by promoting Nrf2 antioxidant pathway. J Neuroinflammation. 2017 Jun 13;14(1):119.
Reference 6 Inhibition of COX-2, mPGES-1 and CYP4A by isoliquiritigenin blocks the angiogenic Akt signaling in glioma through ceRNA effect of miR-194-5p and lncRNA NEAT1. J Exp Clin Cancer Res. 2019 Aug 22;38(1):371.
Reference 7 Suppression of lung cancer progression by isoliquiritigenin through its metabolite 2, 4, 2', 4'-Tetrahydroxychalcone. J Exp Clin Cancer Res. 2018 Oct 3;37(1):243.
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