Isobavachalcone - 10mM in DMSO , CAS No.20784-50-3

CAS: 20784-50-3 Cat. No.: I422520 Molecular Weight: 324.38

GRADE & PURITY 10mM in DMSO

Synonyms

4-Hydroxyisocordoin | AC-34001 | CHEBI:28106 | Isobavachalcone, >=98% (HPCE) | ZWO2SC993A | 2-PROPEN-1-ONE, 1-(2,4-DIHYDROXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-, (2E)- | CCG-267747 | (2E)-1-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Isobavachalcone(Corylifolinin) is a chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma.
An inhibitor of platelet aggregation

Specifications

Synonyms

4-Hydroxyisocordoin | AC-34001 | CHEBI:28106 | Isobavachalcone, >=98% (HPCE) | ZWO2SC993A | 2-PROPEN-1-ONE, 1-(2, 4-DIHYDROXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-, (2E)- | CCG-267747 | (2E)-1-[2, 4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Isobavachalcone inhibits platelet aggregation. Inhibitor of Epstein-Barr virus early antigen (EBV-EA) induction. Isobavachalcone exhibits potent inhibitory effect on skin tumor promotion. Potent inhibitor of MMP-2. Displays DNA strand-scission (cleaving)

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Names and Identifiers

• Canonical Smiles: CC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)O)C
• IUPAC Name: (E)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• InChIKey: DUWPGRAKHMEPCM-IZZDOVSWSA-N
• INCHI: 1S/C20H20O4/c1-13(2)3-9-16-19(23)12-10-17(20(16)24)18(22)11-6-14-4-7-15(21)8-5-14/h3-8,10-12,21,23-24H,9H2,1-2H3/b11-6+
• Isomeric SMILES: CC(=CCC1=C(C=CC(=C1O)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
• Molecular Weight: 324.38
• Reaxy-Rn: 2704389
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2704389&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: 3-prenylated chalcones
• Alternative Parents: 2'-Hydroxychalcones Cinnamylphenols Hydroxycinnamic acids and derivatives Styrenes Resorcinols Benzoyl derivatives Aryl ketones 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Enones Acryloyl compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 3-prenylated chalcone - 2'-hydroxychalcone - Cinnamylphenol - Hydroxycinnamic acid or derivatives - Benzoyl - Aryl ketone - Resorcinol - Styrene - Phenol - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Enone - Acryloyl-group - Alpha,beta-unsaturated ketone - Ketone - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.
• External Descriptors: Chalcones and dihydrochalcones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)

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KIT Tclin Stem cell growth factor receptor (10667 Activities)

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PTPN2 Tchem T-cell protein-tyrosine phosphatase (1317 Activities)

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FGFR2 Tclin Fibroblast growth factor receptor 2 (3405 Activities)

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FGFR1 Tclin Fibroblast growth factor receptor 1 (9149 Activities)

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SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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DUSP3 Tchem Dual specificity protein phosphatase 3 (1161 Activities)

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MET Tclin Hepatocyte growth factor receptor (10718 Activities)

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BACE1 Tchem Beta-secretase 1 (15641 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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Raji (5516 Activities)

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SW480 (6023 Activities)

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A549 (127892 Activities)

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HCT-116 (91556 Activities)

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HepG2 (196354 Activities)

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HUVEC (11049 Activities)

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SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

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Associated Targets(non-human)

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Salmonella typhimurium (15756 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Klebsiella aerogenes (4963 Activities)

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Escherichia coli (133304 Activities)

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Bacillus subtilis (32866 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Bacillus cereus (7522 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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RAW264.7 (28094 Activities)

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Vero (26788 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: 1.66
• Boil Point(°C): ~549.03° C at 760 mmHg
• Melt Point(°C): 210.09°C
• Molecular Weight: 324.400 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 324.136 Da
• Monoisotopic Mass: 324.136 Da
• Topological Polar Surface Area: 77.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 470.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Wu Yueshan, Chang Jing, Ge Juanjuan, Xu Kangyan, Zhou Quan, Zhang Xiaowen, Zhu Ni, Hu Meichun.  (2022)  Isobavachalcone’s Alleviation of Pyroptosis Contributes to Enhanced Apoptosis in Glioblastoma: Possible Involvement of NLRP3.  MOLECULAR NEUROBIOLOGY,  59  (11): (6934-6955).  [PMID:36053436] [10.1007/s12035-022-03010-2]

2. Lin Shuai, Cai Hui, Song Xuemei.  (2024)  Synergy between isobavachalcone and doxorubicin suppressed the progression of anaplastic thyroid cancer through ferroptosis activation.  BRAZILIAN JOURNAL OF MEDICAL AND BIOLOGICAL RESEARCH,      [PMID:39166605] [10.1590/1414-431X2024e13679]

3. Zhirui Du, Xueqiao Yan, Lin Cheng, Haiyu Shen, Guoguo Zhi, Baojie Li, Qian Yu.  (2025)  Luteolin attenuates experimental dry eye disease via dual modulation of macrophage JAK-STAT signaling and corneal epithelial MAPK pathways.  PHYTOMEDICINE,      [PMID:41005053] [10.1016/j.phymed.2025.157300]