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Basic Description
| Synonyms | Xanthohumol | 6754-58-1 | 569-83-5 | 1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one | Xantho-flav | (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one | T4467YT1NT | CHEBI:6633 |
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| Specifications & Purity | 10mM in DMSO |
| Biochemical and Physiological Mechanisms | p97 ATPase (VCP) inhibitor. Binds to the N domain of p97, impairing autophagosome function and maturation. Inhibits proliferation and induces apoptosis in a variety of human cancer cell lines. Also inhibits DGAT in rat liver microsomes (IC50= 50.3μM). |
| Storage Temp | Protected from light,Store at -80°C |
| Shipped In | Ice chest + Ice pads |
Associated Targets(Human)
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)
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CASP3 Tchem Caspase-3 (3632 Activities)
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PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)
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MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)
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PRKCA Tchem Protein kinase C alpha (5923 Activities)
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PRKCQ Tchem Protein kinase C theta (3319 Activities)
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Homo sapiens (32628 Activities)
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BGC-823 (3035 Activities)
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Caco-2 (12174 Activities)
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CCRF-CEM (65223 Activities)
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DU-145 (51482 Activities)
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HT-29 (80576 Activities)
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MCF7 (126967 Activities)
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NCI-H1975 (4994 Activities)
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PC-3 (62116 Activities)
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SGC-7901 (2773 Activities)
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T98G (1524 Activities)
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U-87 MG (3946 Activities)
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A549 (127892 Activities)
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HEK293 (82097 Activities)
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HepG2 (196354 Activities)
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NCI-H460 (60772 Activities)
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HUVEC (11049 Activities)
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Ishikawa (877 Activities)
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LNCaP (8286 Activities)
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HeLa (62764 Activities)
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SETD7 Tchem Histone-lysine N-methyltransferase SETD7 (390 Activities)
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DGAT1 Tclin Diacylglycerol O-acyltransferase 1 (1719 Activities)
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Liver (3974 Activities)
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MAPK3 Tchem Mitogen-activated protein kinase; ERK1/ERK2 (651 Activities)
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MAPK13 Tchem MAP kinase p38 (1586 Activities)
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NFKB2 Tchem Nuclear factor NF-kappa-B complex (2307 Activities)
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LY96 Tchem Lymphocyte antigen 96 (117 Activities)
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LNCaP C4-2 (165 Activities)
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Associated Targets(non-human)
Ttr Transthyretin (14 Activities)
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PTGES Prostaglandin E synthase (10 Activities)
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Plasmodium falciparum (966862 Activities)
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Mus musculus (284745 Activities)
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Rattus norvegicus (775804 Activities)
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Human immunodeficiency virus 1 (70413 Activities)
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MEF (1005 Activities)
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RAW264.7 (28094 Activities)
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BV-2 (3710 Activities)
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TRXR Thioredoxin reductase (20 Activities)
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Nqo1 NAD(P)H dehydrogenase [quinone] 1 (1058 Activities)
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Akt1 RAC-alpha serine/threonine-protein kinase (147 Activities)
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Bcl2l1 Bcl-2-like protein 1 (1 Activities)
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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 | (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one |
|---|---|
| INCHI | InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+ |
| InChi Key | ORXQGKIUCDPEAJ-YRNVUSSQSA-N |
| Canonical SMILES | CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C |
| Isomeric SMILES | CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O)C |
| WGK Germany | 3 |
| PubChem CID | 639665 |
| Molecular Weight | 354.4 |
Certificates
Certificate of Analysis(COA)
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Chemical and Physical Properties
| Sensitivity | Light Sensitive,Air Sensitive,Heat Sensitive |
|---|---|
| Melt Point(°C) | 159 °C |
Safety and Hazards(GHS)
| Pictogram(s) | GHS09, GHS07 |
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| Signal | Warning |
| Hazard Statements | H317:May cause an allergic skin reaction H400:Very toxic to aquatic life |
| Precautionary Statements | P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P501:Dispose of contents/container to ... P272:Contaminated work clothing should not be allowed out of the workplace. P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention. P362+P364:Take off contaminated clothing and wash it before reuse. P391:Collect spillage. |
| WGK Germany | 3 |
Related Documents
Citations of This Product
| 1. Fa-Li Zhang, Liu Yang, Wei-Hao He, Ling-Jun Xie, Fei Yang, Ying-Hui Wang, Ai-Guo Huang. (2023) In vivo antibacterial activity of medicinal plant Sophora flavescens against Streptococcus agalactiae infection. JOURNAL OF FISH DISEASES, 46 (9): (977-986). [PMID:37294673] [10.1111/jfd.13818] |
References
| 1. Fa-Li Zhang, Liu Yang, Wei-Hao He, Ling-Jun Xie, Fei Yang, Ying-Hui Wang, Ai-Guo Huang. (2023) In vivo antibacterial activity of medicinal plant Sophora flavescens against Streptococcus agalactiae infection. JOURNAL OF FISH DISEASES, 46 (9): (977-986). [PMID:37294673] [10.1111/jfd.13818] |