Mitraphylline - Moligand™,≥98% , CAS No.509-80-8

CAS: 509-80-8 Cat. No.: M695130 Molecular Weight: 368.43 EC Number: 208-106-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

Methyl (1'S,3R,4a'S,5a'S,10a'R)-1'-methyl-2-oxo-4a',5',5a',7',8',10a'-hexahydro-1'H,10'H-spiro[indoline-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate | Rubradinine‌ | Ajmalicine oxindole B‌

Storage

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

Shipped In

Wet ice

Overview

Mitraphylline is the major pentacyclic oxindolic alkaloid presented in Uncaria tomentosa. Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils. Mitraphylline exhibits antiproliferative activity in human glioma and neuroblastoma cell lines. Mitraphylline can inhibit interleukin release in vivo.

Specifications

Synonyms

Methyl (1'S, 3R, 4a'S, 5a'S, 10a'R)-1'-methyl-2-oxo-4a', 5', 5a', 7', 8', 10a'-hexahydro-1'H, 10'H-spiro[indoline-3, 6'-pyrano[3, 4-f]indolizine]-4'-carboxylate | Rubradinine‌ | Ajmalicine oxindole B‌

Specifications & Purity

Moligand™, ≥98%

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

Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1C2CN3CCC4(C3CC2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
• IUPAC Name: methyl (1S,4aS,5aS,6R,10aR)-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate
• InChIKey: JMIAZDVHNCCPDM-DAFCLMLCSA-N
• INCHI: 1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1
• Isomeric SMILES: C[C@H]1[C@H]2CN3CC[C@]4([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
• Alternate CAS: 509-80-8
• NSC Number: 717700
• MeSH Entry Terms: methyl (19alpha)-19-methyl-2-oxoformosanan-16-carboxylate;mitraphylline
• Molecular Weight: 368.43
• Reaxy-Rn: 631943
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=631943&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indolizidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indolizidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolizidines
• Alternative Parents: Indolines Aralkylamines Piperidines N-alkylpyrrolidines Benzenoids Vinylogous esters Methyl esters Enoate esters Trialkylamines Secondary carboxylic acid amides Amino acids and derivatives Lactams Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indole or derivatives - Dihydroindole - Indolizidine - Aralkylamine - Piperidine - N-alkylpyrrolidine - Benzenoid - Pyrrolidine - Methyl ester - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Vinylogous ester - Carboxamide group - Amino acid or derivatives - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Carboxylic acid ester - Lactam - Azacycle - Oxacycle - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.
• External Descriptors: indolizines

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)

GAMG (120 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

• Sensitivity: light sensitive；Moisture sensitive
• Molecular Weight: 368.400 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 368.174 Da
• Monoisotopic Mass: 368.174 Da
• Topological Polar Surface Area: 67.900 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 692.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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