Calycosin (Cyclosin) is a natural active compound with anti-oxidative and anti-inflammation activity.
Calycosin, a phytoestrogen isoflavone, may be used to promote and study its mechanisms of angiogenesis via interaction with the estrogen receptor and mitogen-activated protein kinase (MAPK) signaling pathway. Calycosin may be used to study its function and role in neuroprotection via prevention of reperfusion injury. Calycosin may be used as a calcium channel blocker. Calycosin can be used to study its role in protection of HUVECs from advanced glycation end products-induced macrophage infiltration.

Specifications

Sinónimos

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Isoflavone and phytoestrogen isolated froma traditional Chinese medicinal herb. Calycosin induces angiogenesis in HUVEC and promotes proliferation of estrogen-receptor positive cells in vivo and in vitro. Also functions as a vasorelaxant on rat thoracic a

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

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Nombres e identificadores

Sonrisas canónicas	COC1=C(C=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)O)O
IUPAC Name	7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one
InChIKey	ZZAJQOPSWWVMBI-UHFFFAOYSA-N
INCHI	1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3
Isómeros SMILES	COC1=C(C=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)O)O
WGK Alemania	3
Peso molecular	284.26
Reaxy-Rn	1292488
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1292488&ln=

Documentation

📋 Safety Data Sheet (SDS)

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📊 Datasheet

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🔬 Specification Sheet

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Phenylpropanoids and polyketides
  - Clase Isoflavonoids
    - Subclass O-methylated isoflavonoids
      - Level5 4'-O-methylated isoflavonoids
        Level6 3'-hydroxy,4'-methoxyisoflavonoids

Kingdom	Organic compounds
Superclass	Phenylpropanoids and polyketides
Clase	Isoflavonoids
Subclass	O-methylated isoflavonoids
Intermediate Tree Nodes	4'-O-methylated isoflavonoids
Direct Parent	3'-hydroxy,4'-methoxyisoflavonoids
Alternative Parents	4'-O-methylisoflavones Hydroxyisoflavonoids Isoflavones Chromones Methoxyphenols Anisoles Phenoxy compounds Methoxybenzenes 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Pyranones and derivatives Heteroaromatic compounds Oxacyclic compounds Hydrocarbon derivatives Organic oxides
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	4p-o-methylisoflavone - 3'-hydroxy,4'-methoxyisoflavonoid - Isoflavone - Hydroxyisoflavonoid - Chromone - Methoxyphenol - 1-benzopyran - Benzopyran - Phenoxy compound - Phenol ether - Anisole - Methoxybenzene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Pyranone - Phenol - Pyran - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Ether - Organoheterocyclic compound - Oxacycle - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Aromatic heteropolycyclic compound
Descripción	This compound belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.
External Descriptors	an isoflavone
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

Estructura 3D

Objetivos asociados (humanos)

POLB Tchem DNA polymerase beta (23632 Activities)

Discover Target: POLB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HT-1080 (3966 Activities)

Peso molecular	284.260 g/mol
XLogP3	2.400
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	284.068 Da
Monoisotopic Mass	284.068 Da
Topological Polar Surface Area	76.000 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	432.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

1. Lei He, Qian Hu, Liyang Wei, Xuliyang Ge, Ning Yu, Ying Chen. (2023) Unravelling dynamic changes in non-volatile and volatile metabolites of pulses during soaking: An integrated metabolomics approach. FOOD CHEMISTRY, [PMID:37141754] [10.1016/j.foodchem.2023.136231]
2. Jie Zhao, Lin Huang, Renjie Li, Zhuangwei Zhang, Jin Chen, Hongjin Tang. (2022) Insights from multi-spectroscopic analysis and molecular modeling to understand the structure–affinity relationship and the interaction mechanism of flavonoids with gliadin. Food & Function, 13 (9): (5061-5074). [PMID:35404372] [10.1039/D1FO03816H]
3. Hongjin Tang, Lin Huang, Dongsheng Zhao, Chunyong Sun, Ping Song. (2020) Interaction mechanism of flavonoids on bovine serum albumin: Insights from molecular property-binding affinity relationship. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:32480277] [10.1016/j.saa.2020.118519]
4. Jie Zhao, Lin Huang, Chunyong Sun, Dongsheng Zhao, Hongjin Tang. (2020) Studies on the structure-activity relationship and interaction mechanism of flavonoids and xanthine oxidase through enzyme kinetics, spectroscopy methods and molecular simulations. FOOD CHEMISTRY, [PMID:32330646] [10.1016/j.foodchem.2020.126807]
5. Wang Liwei, Zhang Lu, Yun Yang, Liang Tingting, Yan Chaoqun, Mao Zhuoya, Zhang Jingfang, Liu Baoshe, Zhang Jian, Liang Taigang. (2024) Protective effect of astragaloside IV against zinc oxide nanoparticles induced human neuroblastoma SH-SY5Y cell death: a focus on mitochondrial quality control. MOLECULAR AND CELLULAR BIOCHEMISTRY, [PMID:39630360] [10.1007/s11010-024-05172-0]
6. Haolin Zhang, Jingjing Zhang, Hui Cao, Petra Högger, Randolph Arroo, Mohamed A. Farag, Avi Shpigelman, Jianbo Xiao, Chunlin Li. (2025) Amination of Flavonoids Possessing a Pyrogallol Group in Cell Culture Medium at 37°C. Food Frontiers, 6 (2): (1058-1078). [PMID:] [10.1002/fft2.70002]
7. Heng Wang, Zhaofei Liu, Xiangjun Xu, Haitao Zhang, Lei He, Ming Li. (2025) Calycosin Protects Against Chronic Prostatitis via Regulating Cellular Pyroptosis. AMERICAN JOURNAL OF REPRODUCTIVE IMMUNOLOGY, 93 (5): (e70084). [PMID:40349356] [10.1111/aji.70084]
8. Yixuan Guo, Wenqian Liu, Bingsen Qi, Ziyi Liu, Jiaxin Wang, Le Yang, Jingcun Sun, Jinlong Qi. (2025) Integrating network pharmacology, molecular docking and experimental verification to explore the protective effect of Buyang Huanwu Decoction on cerebral ischemic stroke. Results in Chemistry, [PMID:] [10.1016/j.rechem.2025.102856]

Calycosin - 10mM in DMSO , CAS No.20575-57-9

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📋 Safety Data Sheet (SDS)

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