Paeoniflorin - ≥98%(HPLC) , CAS No.23180-57-6

CAS: 23180-57-6 Cat. No.: P101691 Molecular Weight: 480.46 EC Number: 245-476-2 PubChem CID: 442534

GRADE & PURITY ≥98%(HPLC)

Synonyms

AB01566855_01 | ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methylbenzoate | Q-100296 | SCHEMBL549033 | Q7

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

AB01566855_01 | ((2S, 2aR, 2a1S, 3aR, 4R, 5aR)-4-Hydroxy-2-methyl-2a-(((2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1, 5-dioxa-2, 4-methanocyclobuta[cd]pentalen-2a1-yl)methylbenzoate | Q-100296 | SCHEMBL549033 | Q7

Specifications & Purity

≥98%(HPLC)

Storage

Room temperature

Shipped In

Normal

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 488189795
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189795
• Canonical Smiles: C[C@@]12C[C@@]3(O)O[C@@H](O1)[C@]5(COC(=O)c4ccccc4)[C@H]3C[C@]25O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O
• IUPAC Name: [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
• InChIKey: YKRGDOXKVOZESV-WRJNSLSBSA-N
• INCHI: 1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1
• Isomeric SMILES: C[C@]12C[C@@]3([C@@H]4C[C@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
• WGK Germany: 3
• PubChem CID: 442534
• Molecular Weight: 480.46

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Terpene glycosides
• Alternative Parents: Hexoses O-glycosyl compounds Aromatic monoterpenoids Benzoic acid esters Bicyclic monoterpenoids Benzoyl derivatives Furofurans Oxepanes 1,3-dioxanes Oxanes Tetrahydrofurans Hemiacetals Cyclic alcohols and derivatives Carboxylic acid esters Secondary alcohols Oxacyclic compounds Acetals Polyols Monocarboxylic acids and derivatives Hydrocarbon derivatives Primary alcohols Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Terpene glycoside - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Aromatic monoterpenoid - Benzoate ester - Pinane monoterpenoid - Nopinane monoterpenoid - Monoterpenoid - Benzoic acid or derivatives - Benzoyl - Furofuran - Oxepane - Meta-dioxane - Monocyclic benzene moiety - Benzenoid - Monosaccharide - Oxane - Tetrahydrofuran - Cyclic alcohol - Secondary alcohol - Hemiacetal - Carboxylic acid ester - Monocarboxylic acid or derivatives - Polyol - Carboxylic acid derivative - Organoheterocyclic compound - Oxacycle - Acetal - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Alcohol - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
• External Descriptors: terpene glycoside

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)

MCF7 (126967 Activities)

Explore this target

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat Sensitive
• Specific Rotation[α]: -14 ° (C=1, MeOH)
• Molecular Weight: 480.500 g/mol
• XLogP3: -1.000
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 480.163 Da
• Monoisotopic Mass: 480.163 Da
• Topological Polar Surface Area: 164.000 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 849.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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

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4. Jingjing Li, Suiyuan Ren, Meng Li, Jingai Bi, Guang Yang, Erguang Li.  (2021)  Paeoniflorin protects against dextran sulfate sodium (DSS)-induced colitis in mice through inhibition of inflammation and eosinophil infiltration.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:33887576] [10.1016/j.intimp.2021.107667]

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6. Xiaolong Sun, Xu Wang, Zhenyu Zhao, Jing Chen, Cheng Li, Gang Zhao.  (2020)  Paeoniflorin inhibited nod-like receptor protein-3 inflammasome and NF-κB-mediated inflammatory reactions in diabetic foot ulcer by inhibiting the chemokine receptor CXCR2.  DRUG DEVELOPMENT RESEARCH,  82  (3): (404-411).  [PMID:33236457] [10.1002/ddr.21763]

7. Jin Wen, Bin Xu, Yuchao Sun, Mengqiao Lian, Yanli Li, Yuan Lin, Dapeng Chen, Yunpeng Diao, Marwan Almoiliqy, Li Wang.  (2019)  Paeoniflorin protects against intestinal ischemia/reperfusion by activating LKB1/AMPK and promoting autophagy.  PHARMACOLOGICAL RESEARCH,      [PMID:31181335] [10.1016/j.phrs.2019.104308]

8. Jianxin Zhang, Fengchun Wang, Huali Wang, Yanna Wang, Yan Wu, Hui Xu, Chen Su.  (2017)  Paeoniflorin inhibits proliferation of endometrial cancer cells via activating MAPK and NF‑κB signaling pathways.  Experimental and Therapeutic Medicine,  14  (6): (5445-5451).  [PMID:29285074] [10.3892/etm.2017.5250]

9. Zhongcheng Ke, Gang Wang, Lei Yang, Huihui Qiu, Hao Wu, Mei Du, Juan Chen, Jie Song, Xiaobin Jia, Liang Feng.  (2017)  Crude terpene glycoside component from Radix paeoniae rubra protects against isoproterenol-induced myocardial ischemic injury via activation of the PI3K/AKT/mTOR signaling pathway.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:28549860] [10.1016/j.jep.2017.05.028]

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12. Gao Jiaming, Guo Hao, Li Junmei, Zhan Min, You Yue, Xin Gaojie, Liu Zixin, Fan Xiaodi, Gao Qinghe, Liu Jianxun, Zhang Yehao, Fu Jianhua.  (2024)  Buyang Huanwu decoction ameliorates myocardial injury and attenuates platelet activation by regulating the PI3 kinase/Rap1/integrin α(IIb)β(3) pathway.  Chinese Medicine,  19  (1): (1-17).  [PMID:39160598] [10.1186/s13020-024-00976-0]

13. Zhang Di, Chen Zhenni, Zhuang Zifeng, Jing Bei, Cao Yong, Li Yixuan, Pan Yuwei, Gao Li, Chen Jiaxu, Zhao Guoping.  (2024)  Danggui Sini Decoction normalizes the intestinal microbiota and serum metabolite levels to treat sciatica.  PHYTOMEDICINE,      [PMID:39059091] [10.1016/j.phymed.2024.155740]

14. Chengcheng Xiao, Peng Wang, Yayun Wang, Jiaxi Zhu, Hai Zhu, Xin Li, Renhe Wang.  (2025)  Network pharmacology prediction and experimental validation to explore the potential mechanism of Danggui Shaoyao San against Acute Kidney Injury.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:40914309] [10.1016/j.jep.2025.120540]

15. Jiarui Liu, Siqi Chen, Zijing Zhang, Xitong Song, Zhiquan Hou, Ziyi Wang, Tao Liu, Liqun Yang, Yunen Liu, Zhonghua Luo.  (2024)  The oxidized hyaluronic acid hydrogels containing paeoniflorin microspheres regulates the polarization of M1/M2 macrophages to promote wound healing.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39515704] [10.1016/j.ijbiomac.2024.137107]

16. Jingyi Hu, Hai Huang, Yuan Che, Chujie Ding, Lu Zhang, Yun Wang, Haiping Hao, Hong Shen, Lijuan Cao.  (2020)  Qingchang Huashi Formula attenuates DSS-induced colitis in mice by restoring gut microbiota-metabolism homeostasis and goblet cell function.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:32941971] [10.1016/j.jep.2020.113394]

17. Shao-Lu Li, Qiyu Duan, Mengfan Wang, Bo Wu, Ning Yu, Genghao Gong, Yunxia Hu.  (2025)  High-performance microporous organic solvent nanofiltration composite membrane prepared from a contorted maleimidoanthracene biscatechol monomer.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.162706]

18. Ru Qu, Ming Li, Ping Li, Ying Song, Biao Dong, Juan Liu, Xuan Mo, Zhenjiang Zech Xu, Xiaochang Huang.  (2025)  Mitigation of P. gingivalis-exacerbated intestinal inflammation by paeoniflorin through alteration of the gut microbiota.  Microbiology Spectrum,      [PMID:40569065] [10.1128/spectrum.00002-24]

19. 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]

20. Xiaoyun Yang, Qin Guo, Yingying Dong, Huanhuan Wang, Mengya Dang, Yangyang Sun, Yuan Gao, Dong Bai.  (2025)  Glycyrrhiza Protein-Based Nanoparticles Enhance the Oral Bioavailability and Analgesic Efficacy of Paeoniflorin.  International Journal of Nanomedicine,      [PMID:41262311] [10.2147/IJN.S532397]

21. Dan Yang, Bo Wu, Ning Yu, Ruohui Zhang, Wenqi Liu, Hao Liu, Wenjing Li, Yunxia Hu, Shao-Lu Li.  (2025)  Molecular design of a multi-functional monomer for the fabrication of high-performance microporous polyamide membrane.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2025.136511]

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23. Longping Jin, Kunmei Su, Maliang Zhang, Xi Du, Zhenhuan Li.  (2026)  Homologous sulfonated PPS fibers reinforced PPS membrane for drug purification under harsh environments.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2026.125385]

24. Xiao-Long Wang, Chang Zhang, De-Shuang Lu, Zhuo-Yue Dong, Bai-Ming Jin, Si-Yuan Wan, Zi-Wen Zhang, Chun-Jing Zhang, Lin Li.  (2026)  Paeoniflorin protects against NAFLD through antioxidant, anti-inflammatory effects and restoration of gut microbiota homeostasis.  Frontiers in Microbiology,      [PMID:41909260] [10.3389/fmicb.2026.1766068]

25. Jiachang Lin, Pei Huang, Yongqi Wang, Jiaxiang Wu, Yushi Jian, Lina Zhu, Huaying Wen, Wenhui Gao, Yingling Miao, He Wang, Xiyong Yu, Chunfang Liu, Yi Zhou.  (2026)  Paeoniflorin-Copper-Coordinated Nanoparticles Targeting Dual Organelles Induce Lung Cancer Apoptosis.  MOLECULAR PHARMACEUTICS,      [PMID:] [10.1021/acs.molpharmaceut.5c01528]