Asimilobine , CAS No.6871-21-2

CAS: 6871-21-2 Cat. No.: A647685 Molecular Weight: 267.32 EC Number: 881-576-8 PubChem CID: 160875

Synonyms

CHEBI:70637 | 6abeta-Noraporphin-2-ol, 1-methoxy- | DTXSID00988410 | Q4H26TGS8S | R-(-)-asimilobine | FS-8822 | UNII-Q4H26TGS8S | (6AR)-5,6,6A,7-TETRAHYDRO-1-METHOXY-4H-DIBENZO(DE,G)QUINOLIN-2-OL | 4H-Dibenzo(de,g)quinolin-2-ol, 5,6,6a,7-tetrahydro-1-meth

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Asimilobine is an aporphine isoquinoline alkaloid isolated from plant species of Magnolia obobata Thun. Asimilobine is a dopamine biosynthesis inhibitor and a serotonergic receptor antagonist. Asimilobine shows an antimalarial and anti-cancer activity

In Vitro

Asimilobine (0.05-0.2 μM; for 24 h) shows a significant inhibition of intracellular dopamine levels in a concentration-dependent manner with an IC 50 value of 0.13 μM. Asimilobine (0.15 μM) inhibits tyrosine hydroxylase (TH) and aromatic L-amino acid decarboxylase (AADC) activities at 24 h. Asimilobine also decreases TH mRNA levels and intracellular cyclic AMP levels. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

IC50& Target:Plasmodium|Dopamine Receptor|serotonergic receptor

Specifications

Synonyms

CHEBI:70637 | 6abeta-Noraporphin-2-ol, 1-methoxy- | DTXSID00988410 | Q4H26TGS8S | R-(-)-asimilobine | FS-8822 | UNII-Q4H26TGS8S | (6AR)-5, 6, 6A, 7-TETRAHYDRO-1-METHOXY-4H-DIBENZO(DE, G)QUINOLIN-2-OL | 4H-Dibenzo(de, g)quinolin-2-ol, 5, 6, 6a, 7-tetrahydro-1-meth

Biochemical and Physiological Mechanisms

Asimilobine is an aporphine isoquinoline alkaloid isolated from plant species of Magnolia obobata Thun. Asimilobine is a dopamine biosynthesis inhibitor and a serotonergic receptor antagonist. Asimilobine shows an antimalarial and anti-cancer activity

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.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: COC1=C(C=C2CCNC3C2=C1C4=CC=CC=C4C3)O
• IUPAC Name: (6aR)-1-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
• InChIKey: NBDNEUOVIJYCGZ-CYBMUJFWSA-N
• INCHI: 1S/C17H17NO2/c1-20-17-14(19)9-11-6-7-18-13-8-10-4-2-3-5-12(10)16(17)15(11)13/h2-5,9,13,18-19H,6-8H2,1H3/t13-/m1/s1
• Isomeric SMILES: COC1=C(C=C2CCN[C@H]3C2=C1C4=CC=CC=C4C3)O
• PubChem CID: 160875
• Molecular Weight: 267.32

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 Naphthols and derivatives Tetrahydroisoquinolines Anisoles Aralkylamines Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Dialkylamines Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Aporphine - Benzoquinoline - Phenanthrene - 2-naphthol - Naphthalene - Quinoline - Tetrahydroisoquinoline - Anisole - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Aralkylamine - Benzenoid - Azacycle - Ether - Secondary aliphatic amine - Secondary amine - Organoheterocyclic compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen 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: isoquinoline 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)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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HT-1080 (3966 Activities)

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SK-MEL-2 (46422 Activities)

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ZR-75-1 (953 Activities)

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A-431 (6446 Activities)

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KB (17409 Activities)

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LNCaP (8286 Activities)

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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P388 (20296 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 267.320 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 267.126 Da
• Monoisotopic Mass: 267.126 Da
• Topological Polar Surface Area: 41.500 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 361.000
• 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