Basic Description

Synonyms	Paeoniflorin \| 23180-57-6 \| Peoniflorin \| Paeonia moutan \| NSC 178886 \| UNII-21AIQ4EV64 \| 21AIQ4EV64 \| CCRIS 6494 \| EINECS 245-476-2 \| PAEONIFLORIN (USP-RS) \| PAEONIFLORIN [USP-RS] \| NSC-178886 \| ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy
Specifications & Purity	10mM in DMSO
Biochemical and Physiological Mechanisms	Adenosine A 1 receptor activator with neuroprotective and antidepressant effects. Upregulates serotonergic systems in vivo. Blood brain barrier permeable.
Storage Temp	Store at -80°C
Shipped In	Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available.

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
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

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Names and Identifiers

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
INCHI	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
InChIKey	YKRGDOXKVOZESV-WRJNSLSBSA-N
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
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

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

Chemical and Physical Properties

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 Å²
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

Citations of This Product

How to Cite Aladdin Scientific Products?

1. Xingyao Pei, Shusheng Tang, Haiyang Jiang, Wenjuan Zhang, Gang Xu, Zonghui Zuo, Zhenhui Ren, Chun Chen, Yao Shen, Cun Li, Daowen Li. (2023) Paeoniflorin recued hepatotoxicity under zinc oxide nanoparticles exposure via regulation on gut-liver axis and reversal of pyroptosis. SCIENCE OF THE TOTAL ENVIRONMENT, 904 (166885).
2. Yuting Xue, Haotian Zhong, Bin Liu, Shuo Qin, Zhengbo Chen, Kai Li, Lirong Zheng, Xia Zuo. (2023) Colorimetric identification of multiple terpenoids based on bimetallic FeCu/NPCs nanozymes. ANALYTICAL BIOCHEMISTRY, 672 (115160).
3. Binbin Hu, Huaqiang Fang, Zhixin Huang, Wenjing Huang, Li Huang, Huijie Liu, Fanzhen Lv, Wei Huang, Xiaolei Wang. (2023) An upconversion nanoplatform based multi-effective theatment for Parkinson’s disease. CHEMICAL ENGINEERING JOURNAL, 465 (142959).
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, 97 (107667).
5. Di ZHANG, Bing YANG, Shi-Quan CHANG, Sheng-Suo MA, Jian-Xin SUN, Lin YI, Xing LI, Hui-Mei SHI, Bei JING, Ya-Chun ZHENG, Chun-Lan ZHANG, Feng-Guo CHEN, Guo-Ping ZHAO. (2021) Protective effect of paeoniflorin on H2O2 induced Schwann cells injury based on network pharmacology and experimental validation. Chinese Journal of Natural Medicines, 19 (90).
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).
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, 146 (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).
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, 206 (160).
10. Shufang Wang, Haiqiang Wang, Yining Liu, Yi Wang, Xiaohui Fan, Yiyu Cheng. (2016) Rapid discovery and identification of anti-inflammatory constituents from traditional Chinese medicine formula by activity index, LC-MS, and NMR.. Scientific Reports, 6 (31000-31000).
11. Shufang Wang, Lulin Chen, Jing Leng, Pinghong Chen, Xiaohui Fan, Yiyu Cheng. (2014) Fragment ion diagnostic strategies for the comprehensive identification of chemical profile of Gui-Zhi-Tang by integrating high-resolution MS, multiple-stage MS and UV information. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 98 (22).
12. Jingyi Hu,Hai Huang,Yuan Che,Chujie Ding,Lu Zhang,Yun Wang,Haiping Hao,Hong Shen,Lijuan Cao. (2020-09-18) Qingchang Huashi Formula attenuates DSS-induced colitis in mice by restoring gut microbiota-metabolism homeostasis and goblet cell function.. Journal of ethnopharmacology, 266 (113394-113394).
13. 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).
14. 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, (155740).

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Paeoniflorin - 10mM in DMSO, high purity , CAS No.23180-57-6