(-)-Huperzine A - Moligand™, ≥98% , CAS No.102518-79-6

CAS: 102518-79-6 Cat. No.: H107336 Molecular Weight: 242.32 EC Number: 600-320-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

(2S)-2-Amino-3-((((R)-2,3-bis(stearoyloxy)propoxy)-(hydroxy)phosphoryl)oxy)propanoicacid | Fordine | SCHEMBL16789797 | Isoselagine | HB0001 | Selagine | Spectrum3_001074 | (-)-huperzine A | (1R,9R,13Z)-1-Amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Acetylcholinesterase inhibitor; active enantiomer.

Specifications

Synonyms

(2S)-2-Amino-3-((((R)-2, 3-bis(stearoyloxy)propoxy)-(hydroxy)phosphoryl)oxy)propanoicacid | Fordine | SCHEMBL16789797 | Isoselagine | HB0001 | Selagine | Spectrum3_001074 | (-)-huperzine A | (1R, 9R, 13Z)-1-Amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Huperzine A, an active Lycopodium alkaloid extracted from traditional Chinese herb, is a potent, selective and reversible acetylcholinesterase (AChE) inhibitor and has been widely used in China for the treatment of Alzheimer's disease

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504758882
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758882
• Canonical Smiles: CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3
• IUPAC Name: (1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
• InChIKey: ZRJBHWIHUMBLCN-ZUZCIYMTSA-N
• INCHI: 1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/t10-,15+/m0/s1
• Isomeric SMILES: CC=C1[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3
• WGK Germany: 3
• RTECS: PB9185700
• UN Number: 1544
• Molecular Weight: 242.32
• Reaxy-Rn: 24107487
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24107487&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass Quinolones and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Quinolones and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Quinolones and derivatives
• Alternative Parents: Pyridinones Aralkylamines Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinolone - Pyridinone - Aralkylamine - Pyridine - Heteroaromatic compound - Lactam - Azacycle - Amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as quinolones and derivatives. These are compounds containing a quinoline moiety which bears a ketone group.
• External Descriptors: Not available

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)

ACHE Tclin Acetylcholinesterase (0 Activities)

Discover Target: ACHE

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

Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Easily soluble in chloroform, soluble in methanol and ethanol, slightly soluble in water
• Sensitivity: Heat Sensitive
• Specific Rotation[α]: -147° (C=0.5,MeOH)
• Melt Point(°C): 232 °C
• Molecular Weight: 242.320 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 242.142 Da
• Monoisotopic Mass: 242.142 Da
• Topological Polar Surface Area: 55.100 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 551.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 1
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Jianjin GUO, Lu BAI, Chi-Tang HO, Sen GUO, Naisheng BAI.  (2023)  Chemical characterization, multivariate analysis and in vitro bioactivity evaluation of the roots of Fraxinus mandshurica.  CHINESE JOURNAL OF ANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.cjac.2023.100303]

2. Nan Zhao, Dan Liu, Yi Wang, Xiaozhe Zhang, Lihua Zhang.  (2022)  Screening and identification of anti-acetylcholinesterase ingredients from Tianzhi granule based on ultrafiltration combined with ultra-performance liquid chromatography-mass spectrometry and in silico analysis.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:35973628] [10.1016/j.jep.2022.115641]

3. Peiqi Luo, Liping Wang, Lixia Jiang, Jie Sun, Yafeng Li, Huihui Liu, Caiqiao Xiong, Zongxiu Nie.  (2020)  Application of Graphdiyne in Surface-Assisted Laser Desorption Ionization Mass Spectrometry.  ACS Applied Materials & Interfaces,      [PMID:33378159] [10.1021/acsami.0c18280]

4. Liping Zhao, Ge Yang, Linsen Li, Chao Zhu, Yao Ma, Feng Qu.  (2020)  Aptamer-functionalized magnetic nanoparticles conjugated organic framework for immobilization of acetylcholinesterase and its application in inhibitors screening.  ANALYTICA CHIMICA ACTA,      [PMID:33218485] [10.1016/j.aca.2020.10.024]

5. Xiao Tian, Sen Guo, Shanshan Zhang, Peisheng Li, Tianyi Wang, Chi-Tang Ho, Min-Hsiung Pan, Naisheng Bai.  (2019)  Chemical characterization of main bioactive constituents in Paeonia ostii seed meal and GC-MS analysis of seed oil.  JOURNAL OF FOOD BIOCHEMISTRY,  44  (1): (e13088).  [PMID:31646682] [10.1111/jfbc.13088]

6. Sen Guo, Li Liu, Shanshan Zhang, Chuang Yang, Wenping Yue, Haoan Zhao, Chi-Tang Ho, Junfeng Du, Hai Zhang, Naisheng Bai.  (2019)  Chemical characterization of the main bioactive polyphenols from the roots of Morus australis (mulberry).  Food & Function,  10  (10): (6915-6926).  [PMID:31588440] [10.1039/C9FO01457H]

7. Wei Li, Qian Liu, Shimian Cheng, Shanren Li, Yongbiao Zheng.  (2019)  New Sesquiterpenoids from the Fermented Broth of Termitomyces albuminosus and Their Anti-Acetylcholinesterase Activity.  MOLECULES,  24  (16): (2980).  [PMID:31426402] [10.3390/molecules24162980]

8. Jiqing Yang, Xiaotong Hu, Jia Xu, Xin Liu, Li Yang.  (2018)  Single-Step In Situ Acetylcholinesterase-Mediated Alginate Hydrogelation for Enzyme Encapsulation in CE.  ANALYTICAL CHEMISTRY,      [PMID:29469571] [10.1021/acs.analchem.7b05353]

9. Qiang Fu, Jun Tang, Meng Cui, Zhong Zheng, Zhiqiang Liu, Shuying Liu.  (2015)  Development of ESI-MS-based continuous enzymatic assay for real-time monitoring of enzymatic reactions of acetylcholinesterase.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:25875590] [10.1016/j.jchromb.2015.03.022]

10. Yong-Hao Ye, Cong Li, Jun Yang, Liang Ma, Yu Xiao, Jun Hu, Nasir Ahmed Rajput, Cong-Fen Gao, Ying-Ying Zhang, Ming-Hua Wang.  (2014)  Construction of an immobilised acetylcholinesterase column and its application in screening insecticidal constituents from Magnolia officinalis.  PEST MANAGEMENT SCIENCE,  71  (4): (607-615).  [PMID:25228142] [10.1002/ps.3908]

11. Min Wenao, Wang Weiping, Chen Jianrong, Wang Aijun, Hu Zhide.  (2012)  On-line immobilized acetylcholinesterase microreactor for screening of inhibitors from natural extracts by capillary electrophoresis.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,  404  (8): (2397-2405).  [PMID:22932810] [10.1007/s00216-012-6333-8]

12. Jianjin Guo, Jing Gao, Yan Guo, Lu Bai, Chi-Tang Ho, Naisheng Bai.  (2024)  Characterization, multivariate analysis and bioactivity evaluation of coumarins in the bark of Fraxinus mandshurica.  FITOTERAPIA,      [PMID:38382892] [10.1016/j.fitote.2024.105865]

13. Jianjin Guo, Shaojing Liu, Yan Guo, Lu Bai, Chi-Tang Ho, Naisheng Bai.  (2024)  Chemical characterization, multivariate analysis and comparison of biological activities of different parts of Fraxinus mandshurica.  BIOMEDICAL CHROMATOGRAPHY,  38  (6): (e5861).  [PMID:38501361] [10.1002/bmc.5861]

14. Zhao Fengju, Guo Hui, Yang Wei, Guo Lili, Li Jiaxin, Chen Hanqi.  (2024)  Determination of Acetylcholinesterase Activity Based on Ratiometric Fluorescence Signal Sensing.  JOURNAL OF FLUORESCENCE,      [PMID:38613708] [10.1007/s10895-024-03703-y]

15. Lv Jie, He Chengcai, Cao Jingcheng, Shuai Qiuyan, Liu Xifang, Li Meng, Lin Yulong.  (2024)  Gold nanoclusters/manganese dioxide nanosheets hybrid nanozyme with fluorescence and oxidase-like activity for dual-mode detection of acetylcholinesterase and inhibitors screening.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:39733176] [10.1007/s00216-024-05712-z]

16. Dai-Xu Wei, Duanfang Cai, Youguo Tan, Kezhi Liu, Jin-Wei Dao, Xiang Li, Aikeremujiang Muheremu.  (2024)  Poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxyhexanoate)-based microspheres as a sustained platform for Huperzine A delivery for alzheimer's disease therapy.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39447780] [10.1016/j.ijbiomac.2024.136582]

17. Xin Liu, Irfan Azhar, Habib Khan, Qishu Qu, Miaomiao Tian, Li Yang.  (2019)  Capillary electrophoresis-immobilized enzyme microreactors for acetylcholinesterase assay with surface modification by highly-homogeneous microporous layer.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:31443966] [10.1016/j.chroma.2019.460454]