Nuciferine - analytical standard , CAS No.475-83-2

CAS: 475-83-2 Cat. No.: N115702 Molecular Weight: 295.376 EC Number: 842-235-9

GRADE & PURITY Analytical standard

Synonyms

D-(-)-NUCIFERINE | (-)-Nucipherine | Q7067904 | 1,2-Dimethoxy-6abeta-aporphine | l-Nuciferine | s3821 | VLT 049 | MFCD01664592 | BS-42200 | HY-N0049 | (R)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline | 6a-beta-APORPHINE, 1,2-DIMETH

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

D-(-)-NUCIFERINE | (-)-Nucipherine | Q7067904 | 1, 2-Dimethoxy-6abeta-aporphine | l-Nuciferine | s3821 | VLT 049 | MFCD01664592 | BS-42200 | HY-N0049 | (R)-1, 2-dimethoxy-6-methyl-5, 6, 6a, 7-tetrahydro-4H-dibenzo[de, g]quinoline | 6a-beta-APORPHINE, 1, 2-DIMETH

Specifications & Purity

analytical standard

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard

Names and Identifiers

• Canonical Smiles: CN1CCC2=CC(=C(C3=C2C1CC4=CC=CC=C43)OC)OC
• IUPAC Name: (6aR)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• InChIKey: ORJVQPIHKOARKV-OAHLLOKOSA-N
• INCHI: 1S/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/t15-/m1/s1
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@H]1CC4=CC=CC=C43)OC)OC
• Molecular Weight: 295.376
• Reaxy-Rn: 91203
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=91203&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Aporphines

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Aporphines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Aporphines
• Alternative Parents: Phenanthrenes and derivatives Benzoquinolines Tetrahydroisoquinolines Naphthalenes Anisoles Aralkylamines Alkyl aryl ethers Trialkylamines Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Aporphine - Benzoquinoline - Phenanthrene - Naphthalene - Quinoline - Tetrahydroisoquinoline - Anisole - Aralkylamine - Alkyl aryl ether - Benzenoid - Tertiary aliphatic amine - Tertiary amine - Organoheterocyclic compound - Azacycle - Ether - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Organopnictogen compound - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
• 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)

TYR Tclin Tyrosinase (717 Activities)

Discover Target: TYR

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

ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

Discover Target: ADRA1D

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

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

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

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

Discover Target: HTR2C

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

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

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

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

Discover Target: ADRA1B

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

HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

Discover Target: HTR2B

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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 295.400 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 295.157 Da
• Monoisotopic Mass: 295.157 Da
• Topological Polar Surface Area: 21.700 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 401.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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. Yuhuan Chen, Qiwen Chen, Xiaozhong Wang, Fan Sun, Yawei Fan, Xiaoru Liu, Hongyan Li, Zeyuan Deng.  (2019)  Hemostatic action of lotus leaf charcoal is probably due to transformation of flavonol aglycons from flavonol glycosides in traditional Chinses medicine.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:31678413] [10.1016/j.jep.2019.112364]

2. Li Zizhuo, Chen Yaodong, An Tingting, Liu Pengfei, Zhu Jiyuan, Yang Haichao, Zhang Wei, Dong Tianxiu, Jiang Jian, Zhang Yu, Jiang Maitao, Yang Xiuhua.  (2019)  RETRACTED ARTICLE: Nuciferine inhibits the progression of glioblastoma by suppressing the SOX2-AKT/STAT3-Slug signaling pathway.  JOURNAL OF EXPERIMENTAL & CLINICAL CANCER RESEARCH,  38  (1): (1-15).  [PMID:30922391] [10.1186/s13046-019-1134-y]

3. Lina Zhang, Jinghua Gao, Peng Tang, Li Chong, Yue Liu, Peng Liu, Xin Zhang, Li Chen, Chen Hou.  (2018)  Nuciferine inhibits LPS-induced inflammatory response in BV2 cells by activating PPAR-γ.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:30056259] [10.1016/j.intimp.2018.07.015]

4. Shixiang Chen, Bochen Wei, Lili Wen, Penglian Wei, Yunlin Fu.  (2024)  Metabolomics analysis of bioactive compositions of Michelia macclurei Dany and its antioxidant and enzyme inhibitory activities.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  105  (1): (635-648).  [PMID:39230063] [10.1002/jsfa.13860]