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Basic Description
| Synonyms | Liquiritigenin | 578-86-9 | 4',7-Dihydroxyflavanone | (S)-7-Hydroxy-2-(4-hydroxyphenyl)chroman-4-one | (2S)-liquiritigenin | 5-DEOXYFLAVANONE | Menerba | (-)-liquiritigenin | LIQUIRTIGENIN | 7-hydroxy-2-(4-hydroxy-phenyl)-chroman-4-one | UNII-T194LKP9W6 | T194LKP9W6 | CHEBI:2877 |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Biochemical and Physiological Mechanisms | Liquiritigenin is a flavanone found in Radix glycyrrhizae and shown to induce apoptosis in SMM-721 cells by disruption of the mitochondrial membrane potential and increased production of reactive oxygen species |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
Liquiritigenin is a flavonoid and an estrogenic compound found in licorice (Glycyrrhizae radix) root extract and several other plants. Application： |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Phenylpropanoids and polyketides
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Class
Flavonoids
- Subclass Flavans
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Class
Flavonoids
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Superclass
Phenylpropanoids and polyketides
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Flavans |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavanones |
| Alternative Parents | 7-hydroxyflavonoids 4'-hydroxyflavonoids Chromones Aryl alkyl ketones Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Oxacyclic compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 4'-hydroxyflavonoid - 7-hydroxyflavonoid - Hydroxyflavonoid - Flavanone - Chromone - Chromane - 1-benzopyran - Benzopyran - Aryl alkyl ketone - Aryl ketone - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Ketone - Oxacycle - Organoheterocyclic compound - Ether - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. |
| External Descriptors | Flavanones |
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Associated Targets(Human)
CYP19A1
Tclin
Aromatase (1 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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ESR1
Tclin
Estrogen receptor alpha (17718 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CYP19A1
Tclin
Cytochrome P450 19A1 (6099 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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TYR
Tclin
Tyrosinase (717 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ACHE
Tclin
Acetylcholinesterase (18204 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
XDH
Tclin
Xanthine dehydrogenase (1038 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ESR2
Tclin
Estrogen receptor beta (9272 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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JUN
Tchem
Proto-oncogene c-JUN (434 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CYP1B1
Tchem
Cytochrome P450 1B1 (1148 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MMP3
Tchem
Matrix metalloproteinase 3 (3433 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CYP1A1
Tchem
Cytochrome P450 1A1 (1169 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MMP7
Tchem
Matrix metalloproteinase 7 (1073 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MMP1
Tchem
Matrix metalloproteinase-1 (7046 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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YES1
Tclin
Tyrosine-protein kinase YES (2781 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CCRF-CEM (65223 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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DU-145 (51482 Activities)
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HCT-8 (3484 Activities)
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HL-60 (67320 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HT-1080 (3966 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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K562 (73714 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MCF7 (126967 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PANC-1 (6144 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SGC-7901 (2773 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SW480 (6023 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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U-937 (7138 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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A549 (127892 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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T47D (39041 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HCT-116 (91556 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HepG2 (196354 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Ishikawa (877 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HeLa (62764 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MDA-MB-231 (73002 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RELA
Tchem
Nuclear factor NF-kappa-B p65 subunit (627 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PSMB5
Tclin
Proteasome Macropain subunit MB1 (2451 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Associated Targets(non-human)
NA
Neuraminidase (1107 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mmp13
Matrix metalloproteinase 13 (19 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mmp2
Matrix metalloproteinase-2 (12 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Hdac6
Histone deacetylase 6 (222 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Ptpn1
Protein-tyrosine phosphatase 1B (270 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mmp9
Matrix metalloproteinase 9 (38 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mus musculus (284745 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Rattus norvegicus (775804 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Influenza A virus (11224 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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B16 (5829 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MDCK (10148 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RAW264.7 (28094 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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rep
Replicase polyprotein 1ab (378 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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BCHE
Cholinesterase (8742 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Prevotella intermedia (369 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Nfe2l2
Nuclear factor erythroid 2-related factor 2 (214 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
prtC
Collagenase (8 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
SARS-CoV-2 (38078 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| IUPAC Name | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one |
|---|---|
| INCHI | InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1 |
| InChIKey | FURUXTVZLHCCNA-AWEZNQCLSA-N |
| Smiles | Oc1ccc(cc1)[C@@H]2CC(=O)c3ccc(O)cc3O2 |
| Isomeric SMILES | C1[C@H](OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O |
| WGK Germany | 3 |
| RTECS | DJ2981789 |
| PubChem CID | 114829 |
| Molecular Weight | 256.25 |
| Beilstein | 359378 |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Molecular Weight | 256.250 g/mol |
|---|---|
| XLogP3 | 2.200 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Exact Mass | 256.074 Da |
| Monoisotopic Mass | 256.074 Da |
| Topological Polar Surface Area | 66.800 Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 335.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Citations of This Product
| 1. Xiaoran Ning, Yanhui Ni, Jingjing Cao, Huaxing Zhang. (2023) Liquiritigenin Attenuated Collagen-Induced Arthritis and Cardiac Complication via Inflammation and Fibrosis Inhibition in Mice. CHEMICAL & PHARMACEUTICAL BULLETIN, 71 (4): (269-276). |
| 2. Bin Guo, Xu-Ran Fan, Zhong-Ze Fang, Yun-Feng Cao, Cui-Min Hu, Julin Yang, Yan-Yan Zhang, Rong-Rong He, Xu Zhu, Zhen-Wen Yu, Xiao-Yu Sun, Mo Hong, Lu Yang. (2012) Deglycosylation of Liquiritin Strongly Enhances its Inhibitory Potential Towards UDP-Glucuronosyltransferase (UGT) Isoforms. PHYTOTHERAPY RESEARCH, 27 (8): (1232-1236). |
| 3. Hui Cao,Xiaojuan Liu,Nataša Poklar Ulrih,Pradeep K Sengupta,Jianbo Xiao. (2018-09-04) Plasma protein binding of dietary polyphenols to human serum albumin: A high performance affinity chromatography approach.. Food chemistry, 270 (257-263). |
| 4. Na Li,Liyan Liu,Huiqing Luo,Huaqiao Wang,Depo Yang,Feng He. (2020-07-28) Flavanone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics for Mitochondria-Imaging and Zebrafish-Imaging.. Molecules (Basel, Switzerland), 25 ((14)): |
| 5. Yinhuang Gao, Peng Zhao, Chunyan Wang, Keren Fang, Yueqing Pan, Yan Zhang, Zhishuo Miao, Meirong Wang, Minlong Wei, Wei Zou, Menghua Liu, Kang Peng. (2024) Buqi Huoxue Tongnao prescription protects against chronic cerebral hypoperfusion via regulating PI3K/AKT and LXRα/CYP7A1 signaling pathways. PHYTOMEDICINE, 132 (155844). |
| 6. Ziyao Chen, Dongju Zhao, Meng Cheng, Fan Yang, Yining Liu, Jin Chang, Yan Dou. (2024) Female-sensitive multifunctional phytoestrogen nanotherapeutics for tailored management of postmenopausal Alzheimer's disease. Nano Today, 54 (102119). |
| 7. Peng Deng, Qifan Wang, Shengfang Wu, Xiuwen Zhou, Fatih Oz, Qiuming Chen, Zhaojun Wang, Zhiyong He, Jie Chen, Maomao Zeng. (2025) Synergistic effect of spice extracts on multiple hazards formation and sensory markers in beef flavoring. Food Bioscience, 65 (106099). |
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