Shikonin - 10mM in DMSO , CAS No.517-89-5

CAS: 517-89-5 Cat. No.: S424442 Molecular Weight: 288.30 EC Number: 610-730-7 PubChem CID: 479503

GRADE & PURITY 10mM in DMSO

Synonyms

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione | Shikonin S | (+)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone | 2-(2-methoxyethoxyl)ethyl 4-methylbenzenesulfonate | shikonin | (R)-5,8-Dihydroxy-2-(1-hydro

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

A naphthoquinone derivative with angiogenesis inhibitor properties.

Specifications

Synonyms

5, 8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1, 4-dione | Shikonin S | (+)-5, 8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1, 4-naphthoquinone | 2-(2-methoxyethoxyl)ethyl 4-methylbenzenesulfonate | shikonin | (R)-5, 8-Dihydroxy-2-(1-hydro

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Shikonin is a naturally occurring active chemical found in the root of Lithospermum erythrorhizon and used as a Chinese herb. The compound is a naphthoquinone derivative and has been shown to have anti-inflammatory and anti-tumor properties, as well as al

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.

Names and Identifiers

• Canonical Smiles: CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• IUPAC Name: 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
• InChIKey: NEZONWMXZKDMKF-SNVBAGLBSA-N
• INCHI: 1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
• Isomeric SMILES: CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• PubChem CID: 479503
• Molecular Weight: 288.30

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthoquinones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoquinones
• Alternative Parents: Bicyclic monoterpenoids Aromatic monoterpenoids Quinones Aryl ketones 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Secondary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthoquinone - Aromatic monoterpenoid - Bicyclic monoterpenoid - Monoterpenoid - Aryl ketone - Quinone - 1-hydroxy-2-unsubstituted benzenoid - Vinylogous acid - Ketone - Secondary alcohol - Hydrocarbon derivative - Alcohol - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
• External Descriptors: alpha-Naphthoquinones

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)

CDC25A Tchem M-phase inducer phosphatase 1 (1 Activities)

Discover Target: CDC25A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CDC25B Tchem M-phase inducer phosphatase 2 (1 Activities)

Discover Target: CDC25B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Molecular Weight: 288.290 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 288.1 Da
• Monoisotopic Mass: 288.1 Da
• Topological Polar Surface Area: 94.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 501.000
• 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

References

1. Chen Xiaohui, Lin Shengrong, Liang Yunbang, Xue Xiaomin, Yasen Miersalijiang.  (2023)  Experimental evidence of shikonin as a novel intervention for anti-inflammatory effects.  NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY,      [PMID:37249613] [10.1007/s00210-023-02542-1]

2. Wenjie Feng, Wanrui Shi, Ze Wang, Yanqi Cui, Xinxin Shao, Shuwei Liu, Li Rong, Yi Liu, Hao Zhang.  (2022)  Enhancing Tumor Therapy of Fe(III)-Shikonin Supramolecular Nanomedicine via Triple Ferroptosis Amplification.  ACS Applied Materials & Interfaces,      [PMID:35944147] [10.1021/acsami.2c11130]

3. Yang Chen, Leting Si, Jinghui Zhang, Hengyuan Yu, Xuesong Liu, Yong Chen, Yongjiang Wu.  (2021)  Uncovering the antitumor effects and mechanisms of Shikonin against colon cancer on comprehensive analysis.  PHYTOMEDICINE,      [PMID:33476976] [10.1016/j.phymed.2021.153460]

4. Yang Chen, Juan Ni, Yun Gao, Jinghui Zhang, Xuesong Liu, Yong Chen, Zhongjian Chen, Yongjiang Wu.  (2020)  Integrated proteomics and metabolomics reveals the comprehensive characterization of antitumor mechanism underlying Shikonin on colon cancer patient-derived xenograft model..  Scientific Reports,  10  (1): (14092-14092).  [PMID:32839531] [10.1038/s41598-020-71116-5]

5. Hongli Guo, Jieyu Sun, Deyi Li, Yahui Hu, Xiaowen Yu, Hu Hua, Xia Jing, Feng Chen, Zhanjun Jia, Jing Xu.  (2019)  Shikonin attenuates acetaminophen-induced acute liver injury via inhibition of oxidative stress and inflammation.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:30818140] [10.1016/j.biopha.2019.108704]

6. Yali Zhang, Tingting Xu, Zheer Pan, Xiangting Ge, Chuchu Sun, Chun Lu, Hongjin Chen, Zhongxiang Xiao, Bing Zhang, Yuanrong Dai, Guang Liang.  (2017)  Shikonin inhibits myeloid differentiation protein 2 to prevent LPS-induced acute lung injury.  BRITISH JOURNAL OF PHARMACOLOGY,  175  (5): (840-854).  [PMID:29243243] [10.1111/bph.14129]

7. Wang Rong, Zhu Liangqin, Wang Jianfei, Zeng Chenglong, Chen Ying, Wei Yan.  (2025)  Electrochemical sensing interface of copper-coordinated polyhistidine/functionalized multi-walled carbon nanotubes for shikonin determination.  JOURNAL OF SOLID STATE ELECTROCHEMISTRY,      [PMID:] [10.1007/s10008-025-06244-x]

8. Zhiyuan Liu, Yaxuan Huang, Rui Sun, Nan Li, Fengyun Xu, Wei Zhang, Wenke Zhang.  (2025)  Polyethylene Glycolated Shikonin-Functionalized Carbon Nanotubes as an Effective Anticancer System Combining Chemotherapy and Photothermal Therapy.  LANGMUIR,      [PMID:40015981] [10.1021/acs.langmuir.4c05257]

9. Shaoyi Cao, Huaqiu Li, Xiaoyan Ye, Xinxing Xing, Yonghuan Xie, Xiangfeng Zeng, Hongjiao Liu, Xing Zhong, Xinyi Yang, Wenxiu Xing, Cairong Zhu, Xiaoping Wu.  (2024)  Shikonin induces the apoptosis and pyroptosis of EGFR-T790M-mutant drug-resistant non-small cell lung cancer cells via the degradation of cyclooxygenase-2.  EUROPEAN JOURNAL OF MEDICAL RESEARCH,      [PMID:39702296] [10.1186/s40001-024-02187-7]

10. Hang Liu, Jie Liu, Saidi ji, Shengfeng Peng, Lei Zhou, Wei Liu.  (2025)  Effects of orange variety on the physiochemical properties of self-secretory extracellular vesicle and its application potential as nutrient-rich beverage.  FOOD RESEARCH INTERNATIONAL,      [PMID:40922200] [10.1016/j.foodres.2025.116972]

11. Wenjie Feng, Wanrui Shi, Shuwei Liu, Huiwen Liu, Yi Liu, Pengfei Ge, Hao Zhang.  (2021)  Fe(III)-Shikonin Supramolecular Nanomedicine for Combined Therapy of Tumor via Ferroptosis and Necroptosis.  Advanced Healthcare Materials,  11  (2): (2101926).  [PMID:34738742] [10.1002/adhm.202101926]

12. Hang Liu, Chen Yang, Xiaolin Wu, Shengfeng Peng, Lei Zhou, David Julian McClements, Wei Liu.  (2025)  Influence of the maturity on the characteristics of orange-derived extracellular vesicles and their delivery performance for curcumin.  FOOD CHEMISTRY,      [PMID:40311575] [10.1016/j.foodchem.2025.144518]

13. Deng Yuchen, Wen Chao, Wang Fang.  (2025)  Citric acid-modified chitosan hydrogel loaded with shikonin promotes skin wound healing.  Journal of Burn Care & Research,      [PMID:40928158] [10.1093/jbcr/iraf175]

14. Jiang Yourang, Tang Xueyong, Wang Ailin, Yang Hua, Jiang Xue, Zhang Yinxin, Lou Fanglu.  (2025)  Shikonin-copper coordination nanoparticles for enhanced antibacterial and antibiofilm activity against Staphylococcus aureus.  Scientific Reports,  15  (1): (39617).  [PMID:41224798] [10.1038/s41598-025-23269-4]

15. Yanhui Cui, Xueqin Wang, Caiyang Lu, Liling Ran, Zirui Guo, Jiayu Yao, Tian Yu, Xuanxi Liu, Fang Li, Changqi Li, Yingcai Meng, Wenhu Zhou.  (2025)  Treating Acute Respiratory Distress Syndrome with a Multifaceted Nanomedicine: Inhibition of PANoptosis and Enhancement of Lung Barrier Integrity.  Materials Today Bio,      [PMID:41560832] [10.1016/j.mtbio.2025.102748]

16. Mei Yang, Guo-ping Wu, Shi-wei Bao, Yang Zhou, Jie-ting Geng, Chan Zhong.  (2026)  Shikonin-loaded bioactive gelatin films with antibacterial activity against Listeria species and antioxidant properties to extend the shelf-life of raw refrigerated beef.  INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY,      [PMID:41538910] [10.1016/j.ijfoodmicro.2026.111625]