Coptisine - Moligand™,≥98% , CAS No.3486-66-6

CAS: 3486-66-6 Cat. No.: C664260 Molecular Weight: 320.32

GRADE & PURITY Moligand™, ≥98%

Synonyms

6,7-Dihydro-[1,3]dioxolo[4',5':7,8]isoquinolino[3,2-a][1,3]dioxolo[4,5-g]isoquinolin-5-ium | 5,6-Dihydro-2,3:9,10-bis(methylenedioxy)dibenzo[a,g]quinolizinium

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Coptisine is an alkaloid from Chinese goldthread, and acts as an efficient uncompetitive IDO inhibitor with a Ki value of 5.8 μM and an IC50 value of 6.3 μM.

Specifications

Synonyms

6, 7-Dihydro-[1, 3]dioxolo[4', 5':7, 8]isoquinolino[3, 2-a][1, 3]dioxolo[4, 5-g]isoquinolin-5-ium | 5, 6-Dihydro-2, 3:9, 10-bis(methylenedioxy)dibenzo[a, g]quinolizinium

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6
• IUPAC Name: 5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene
• InChIKey: XYHOBCMEDLZUMP-UHFFFAOYSA-N
• INCHI: 1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1
• Isomeric SMILES: C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6
• Molecular Weight: 320.32

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Protoberberine alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Protoberberine alkaloids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Protoberberine alkaloids and derivatives
• Alternative Parents: Isoquinolines and derivatives Benzodioxoles Pyridinium derivatives Benzenoids Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Acetals Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Protoberberine skeleton - Isoquinoline - Benzodioxole - Benzenoid - Pyridine - Pyridinium - Heteroaromatic compound - Acetal - Oxacycle - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic cation - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
• External Descriptors: alkaloid

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)

Panel NCI-60 (60 carcinoma cell lines) (1088 Activities)

Explore this target

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

HaCaT (4069 Activities)

Explore this target

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

Associated Targets(non-human)

NA Neuraminidase (1107 Activities)

Discover Target: NA

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

Calf thymus DNA (4845 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 320.300 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 320.092 Da
• Monoisotopic Mass: 320.092 Da
• Topological Polar Surface Area: 40.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 1
• Complexity: 502.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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. Jin Pian, Zhu Fucheng, Zhou Wen, Liu Chen, Li Na, Liu Houmei.  (2023)  Developing magnetic functionalized dendritic fibrous mesoporous silica as advanced adsorbent for quaternary ammonium alkaloids.  MICROCHIMICA ACTA,  190  (12): (1-12).  [PMID:37999777] [10.1007/s00604-023-06053-x]

2. Yang Gao, Shi-Qiao Liu, Jia-Long Wang, Han-Ming Cui, Qiu-Yan Zhang, Lei Wang, Yi-Xin Zhang, Jian Li, Yu Dong, Yuan-Hui Hu.  (2023)  Vitro UPLC analysis and mass method identification, and in vivo or cellular immune anti-inflammatory function of Sanhuang Xiexin Decoction (SHXD).  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:37544343] [10.1016/j.jep.2023.117002]

3. Longlong Gao, Rui Tian, Yong Shao.  (2023)  Photocatalytic Duplex-Based DNAzymes Switched by an Abasic Site.  Chemistry-Switzerland,  5  (3): (1497-1507).  [PMID:] [10.3390/chemistry5030102]

4. Huanyu Guan, Pengfei Li, Qian Wang, Fanli Zeng, Jiashuo Wu, Fangqing Zhang, Shanggao Liao, Yue Shi.  (2022)  Deciphering the chemical constituents of Shengjiang Xiexin decoction by ultrahigh-performance liquid chromatography-quadrupole/orbitrap high-resolution mass spectrometry and the impact of 20 characteristic components on multidrug resistance-associated protein 2 in the vesicular transport assay.  JOURNAL OF SEPARATION SCIENCE,  45  (18): (3459-3479).  [PMID:35838583] [10.1002/jssc.202200370]

5. Lu Shao Hua, Zhang Ming Cai, Zhai Hong Lin, Bi Ke Xin, Zhao Bing Qiang.  (2022)  Rapid Determination in the Quality Control of Chinese Patent Medicine.  Journal of Pharmaceutical Innovation,  17  (4): (1305-1313).  [PMID:] [10.1007/s12247-021-09608-8]

6. Kun Yan, Lancheng Wang, Huimin Zhou, Zhendong Hua, Peng Xu, Hui Xu, Youmei Wang, Bin Di, Chi Hu.  (2021)  Cucurbituril-mediated AIE: An unconventional indicator displacement assay for ketamine detection.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2021.109875]

7. Hanzhi Zhang, Chunli Lou, Jing Li, Jingwu Kang.  (2020)  A gold foil covered fused silica capillary tip as a sheathless interface for coupling capillary electrophoresis-mass spectrometry.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:32540065] [10.1016/j.chroma.2020.461215]

8. Yuehua Hu, Fan Lin, Tao Wu, Ying Wang, Xiao-Shun Zhou, Yong Shao.  (2016)  Fluorescently Sensing of DNA Triplex Assembly Using an Isoquinoline Alkaloid as Selector, Stabilizer, Inducer, and Switch-On Emitter.  Chemistry-An Asian Journal,  11  (14): (2041-2048).  [PMID:27252050] [10.1002/asia.201600459]

9. Jiajia Zhai, Zeping Li, Huifeng Zhang, Zuowei Lu, Yi Zhang, Mo Li, Jian Kang, Zelong Yang, Louyan Ma, Li Ma, Zhengquan Ma, Xiaorui Ma, Fanghong Zhao, Xiaoqing Ma, Yuan Gao, Yuanyuan Zhang, Xiaomiao Li.  (2023)  Coptisine mitigates diabetic nephropathy via repressing the NRLP3 inflammasome.  Open Life Sciences,  18  (1):   [PMID:37197172] [10.1515/biol-2022-0568]