Ammothamnine - analytical standard,Moligand™ , CAS No.16837-52-8

CAS: 16837-52-8 Cat. No.: A111285 Molecular Weight: 264.36 EC Number: 605-514-4

GRADE & PURITY Analytical standard, Moligand™

Synonyms

Pachycarpidine | BDBM50597716 | Oxymatrine | BBL030371 | MLS001215101 | rel-(41S,7aS,13aR,13bR)-10-Oxohexadecahydrodipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine 4-oxide | Matrine 1beta-oxide | Ammothamnine | SCHEMBL13394285 | Oxysophoridine | DTXSID409374

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Alkaloid isolated from Sophora flavescens. Antifribotic. Neuroprotective.

Specifications

Synonyms

Pachycarpidine | BDBM50597716 | Oxymatrine | BBL030371 | MLS001215101 | rel-(41S, 7aS, 13aR, 13bR)-10-Oxohexadecahydrodipyrido[2, 1-f:3', 2', 1'-ij][1, 6]naphthyridine 4-oxide | Matrine 1beta-oxide | Ammothamnine | SCHEMBL13394285 | Oxysophoridine | DTXSID409374

Specifications & Purity

analytical standard, Moligand™

Biochemical and Physiological Mechanisms

Natural antiproliferative and apoptotic compound. Inhibits iNOS expression and TGF-β/Smad pathway in bleomycin-induced pulmonary fibrosis. Antitumor, antiviral and anti-arrhythmia agent. Active in vivo and in vitro .

Storage

Store at 2-8°C, Protected from light, Argon charged

Shipped In

Wet ice

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

Grade

Analytical standard, Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

• Canonical Smiles: C1CC2C3CCC[N+]4(C3C(CCC4)CN2C(=O)C1)[O-]
• IUPAC Name: (1R,2R,9S,17S)-13-oxido-7-aza-13-azoniatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one
• InChIKey: XVPBINOPNYFXID-LHDUFFHYSA-N
• INCHI: 1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-,17?/m0/s1
• Isomeric SMILES: C1C[C@@H]2[C@H]3CCC[N+]4([C@H]3[C@@H](CCC4)CN2C(=O)C1)[O-]
• Molecular Weight: 264.36
• Reaxy-Rn: 753307
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=753307&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Lupin alkaloids
      • Subclass Matrine alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Lupin alkaloids
• Subclass: Matrine alkaloids
• Intermediate Tree Nodes: Not available
• Direct Parent: Matrine alkaloids
• Alternative Parents: Quinolizidinones Naphthyridines Piperidinones Delta lactams Trialkyl amine oxides Tertiary carboxylic acid amides Trisubstituted amine oxides and derivatives Azacyclic compounds Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Matrine - Quinolizidinone - Diazanaphthalene - Naphthyridine - Quinolizidine - Delta-lactam - Piperidinone - Piperidine - Trialkyl amine oxide - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Organoheterocyclic compound - Azacycle - N-oxide - Carboxylic acid derivative - Trisubstituted n-oxide - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic zwitterion - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one skeleton.
• External Descriptors: Quinolizidine alkaloids

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)

MAOA Tclin Monoamine oxidase A (11911 Activities)

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HepG2 (196354 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Hepatitis B virus (7925 Activities)

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Coxsackievirus B3 (1096 Activities)

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Influenza A virus (11224 Activities)

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Enterovirus A71 (1246 Activities)

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MDCK (10148 Activities)

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Blood (6 Activities)

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Tgfbr1 TGF-beta receptor type-1 (52 Activities)

Discover Target: Tgfbr1

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light & air & heat sensitive
• Melt Point(°C): 206℃
• Molecular Weight: 264.360 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 264.184 Da
• Monoisotopic Mass: 264.184 Da
• Topological Polar Surface Area: 38.400 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 400.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 1
• 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 He, Wenjing Wang, Guoli Wei, Yuqing Wang, Yingjie Wei, Jing Wang, Zhenhai Zhang.  (2023)  Sodium alginate combined with oxymatrine ameliorates CCl4-induced chemical hepatic fibrosis in mice.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:37922569] [10.1016/j.intimp.2023.111144]

2. Fa-Li Zhang, Liu Yang, Wei-Hao He, Ling-Jun Xie, Fei Yang, Ying-Hui Wang, Ai-Guo Huang.  (2023)  In vivo antibacterial activity of medicinal plant Sophora flavescens against Streptococcus agalactiae infection.  JOURNAL OF FISH DISEASES,  46  (9): (977-986).  [PMID:37294673] [10.1111/jfd.13818]

3. Shengwei Li, Guangqing Feng, Min Zhang, Xing Zhang, Jihong Lu, Chenyahui Feng, Fangshi Zhu.  (2022)  Oxymatrine attenuates TNBS-induced colinutis in rats through TLR9/Myd88/NF-κB signal pathway.  HUMAN & EXPERIMENTAL TOXICOLOGY,      [PMID:35290143] [10.1177/09603271221078866]

4. Jin Yinshan, Liu Jiannan, Liu Yadong, Liu Yang, Guo Guiying, Yu Shiliang, An Ruihua.  (2020)  Oxymatrine Inhibits Renal Cell Carcinoma Progression by Suppressing β-Catenin Expression.  Frontiers in Pharmacology,      [PMID:32581789] [10.3389/fphar.2020.00808]

5. Yu-Mei Zhao, Lv-Huan Wang, Si-Fan Luo, Qi-Qin Wang, Ruin Moaddel, Ting-Ting Zhang, Zheng-Jin Jiang.  (2018)  Magnetic beads-based neuraminidase enzyme microreactor as a drug discovery tool for screening inhibitors from compound libraries and fishing ligands from natural products.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:30005943] [10.1016/j.chroma.2018.07.031]

6. Haiping Li, Bo Zhang, Fanping Meng, Siyuan Shao, Yufan Xia, Yu Yao.  (2024)  Adsorption, natural attenuation, and microbial community response of ofloxacin and oxolinic acid in marine sediments.  ENVIRONMENTAL POLLUTION,      [PMID:38458522] [10.1016/j.envpol.2024.123738]

7. Huifang Li, Yu Yue, Xiao Wang, Dahuan Liu.  (2025)  An environmentally friendly lithium extraction system utilizing Cyanex 272 as iron-fixed reagent.  DESALINATION,      [PMID:] [10.1016/j.desal.2025.118574]

8. Fan Luo, Changchao Zhang, Yuyang Zhang, Jie Han, Ziteng Wang, Wenge Yang, Yonghong Hu.  (2024)  Determination and analysis of 4-hydroxyphenylacetamide solubility in different solvents by Hansen solubility parameters, solvent effect and thermodynamic properties.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.125673]

9. Siyu Gan, Zhenxing Wang, Chunli Zheng, Zishen Lin, Ai-bin Zhu, Bo Lai.  (2024)  Enhanced Treatment of Antimony Mine Wastewater by Sulfidated Micro Zerovalent Iron (S-mZVI).  LANGMUIR,      [PMID:39358310] [10.1021/acs.langmuir.4c02741]

10. Qingsheng Wang, Wen Huang, Qian Sun, Mengqi Le, Lili Cai, Yong-Guang Jia.  (2025)  Facially amphiphilic skeleton-derived antibacterial crown ether/silver ion complexes.  Soft Matter,      [PMID:39989433] [10.1039/D4SM01192A]

11. Wenjun Rao, Xin Li, Linghua Ouyang, Shuilan Zhu, Shuai Hu, Linfeng Yuan, Jinying Zhou.  (2024)  Investigation of the quality of rapeseed oil derived from different varieties and growth periods based on GC-IMS technique.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.111357]

12. Yinfeng Li, Huaiyuan Cao, Zixiao Xue, Ran Luo, Xuejie Lin, Yuhua Xue, Long Zhang, Jin He.  (2024)  Optical bonding utilizing aqueous Al2O3–P2O5-lactate sol-gel adhesives.  CERAMICS INTERNATIONAL,      [PMID:] [10.1016/j.ceramint.2024.06.169]

13. Qiuyan Lin, Na Zheng, Qirui An, Zhifei Xiu, Xiaoqian Li, Huicheng Zhu, Changcheng Chen, Yunyang Li, Sujing Wang.  (2024)  Phthalate monoesters accumulation in residential indoor dust and influence factors.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:39047842] [10.1016/j.scitotenv.2024.174900]

14. Runzhe Liu, Zihao Wang, Wenbo Yang, Jinzhe Cao, Shengyang Tao.  (2024)  Self-optimizing Bayesian for continuous flow synthesis process.  Digital Discovery,  3  (10): (1958-1966).  [PMID:] [10.1039/D4DD00223G]

15. Xue Tiange, Huang Zeya, Zhang Xiaotian, Meng Meng, Yu Shixiang, Chen Tian, Fu Renli.  (2024)  Study on high temperature reliability of electrical interconnection material of SiC pressure sensor.  JOURNAL OF MATERIALS SCIENCE-MATERIALS IN ELECTRONICS,  35  (10): (1-12).  [PMID:] [10.1007/s10854-024-12308-x]

16. Wanyu Li, Jiamin Ye, Zhiwen Jia, Haipeng Yu, Linghao Li, Hong Wang, Enchen Jiang, Yan Sun, Xiwei Xu.  (2024)  The full utilization of bagasse via deep eutectic solvent pretreatment for low-condensed lignin and cellulose smart indicator film.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.151653]

17. Yanshi Wang, Shaojie Yang, Shanshan Zhang, Xin Wu.  (2020)  Oxymatrine Inhibits Proliferation and Migration of Vulvar Squamous Cell Carcinoma Cells via Attenuation of the RAS/RAF/MEK/ERK Pathway.  Cancer Management and Research,      [PMID:32256113] [10.2147/CMAR.S245696]

18. Wei Zhou, Yikun Liu, Xiaoyan Liao, Zilin Chen.  (2019)  Capillary electrophoresis-mass spectrometry using robust poly(ether ether ketone) capillary for tolerance to high content of organic solvents.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:30718059] [10.1016/j.chroma.2019.01.070]

19. Juan Zhang, Zilin Chen.  (2013)  Determination of Matrine and Oxymatrine in Sophora Flavescens by Nonaqueous Capillary Electrophoresis-Electrospray Ionization-Ion Trap-Mass Spectrometry.  ANALYTICAL LETTERS,      [PMID:] [10.1080/00032719.2012.726684]

20. Liyun Ma, Si-Min Liu, Lin Yao, Li Xu.  (2014)  Preparation and chromatographic performance evaluation of cucurbit[7]uril immobilized silica.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:25528071] [10.1016/j.chroma.2014.12.002]

21. Di Sun, Wenze Cheng, Zheng Li, Hui Yao, Mafeng Liu, Mingshu Wang, Shun Chen, Yukun Zhu, Jingming Wang, Yuan Deng, Funeng Xu, Xumin Ou, Renyong Jia, Dekang Zhu, Xinxin Zhao, Qiao Yang, Ying Wu, Shaqiu Zhang, Juan Huang, Bin Tian, Yu He, Zhen Wu, Anchun Cheng.  (2025)  Targeting the Pan-Viral Host Protein HSPA8 with Oxymatrine as a Novel Therapy against Duck Hepatitis A Virus Infection.  POULTRY SCIENCE,      [PMID:41455214] [10.1016/j.psj.2025.106336]