Maytansine - Moligand™, ≥98% , CAS No.35846-53-8

CAS: 35846-53-8 Cat. No.: M647545 Molecular Weight: 692.2 EC Number: 252-754-7

GRADE & PURITY Moligand™, ≥98%

Synonyms

Maitansine | Maytansin | NSC 153858 | MTS | N-Acetyl-N-methyl-L-alanine [1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*)]-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Maytansine is a highly potent microtubule-targeted compound that induces mitotic arrest and kills tumor cells at subnanomolar concentrations.

In Vitro

Maytansine, at 6x10 -8 M, irreversibly inhibits cell division in eggs of sea urchins and clams. Maytansine causes the disappearance of a mitotic apparatus or prevents one from forming if added at early stages. Maytansine inhibits in vitro polymerization of tubulin. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

Maitansine | Maytansin | NSC 153858 | MTS | N-Acetyl-N-methyl-L-alanine [1S-(1R*, 2S*, 3R*, 5R*, 6R*, 16E, 18E, 20S*, 21R*)]-11-chloro-21-hydroxy-12, 20-dimethoxy-2, 5, 9, 16-tetramethyl-8, 23-dioxo-4, 24-dioxa-9, 22-diazatetracyclo[19.3.1.110, 14.03, 5]hexacosa-10, 12, 14(

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Maytansine is a highly potent microtubule-targeted compound that induces mitotic arrest and kills tumor cells at subnanomolar concentrations.

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: O[C@]([C@@H](/C=C/C=C(CC1=CC2=C(C(OC)=C1)Cl)\C)OC)(C[C@H](O3)[C@H]([C@H]4[C@](C)([C@H](CC(N2C)=O)OC([C@@H](N(C)C(C)=O)C)=O)O4)C)NC3=O
• IUPAC Name: [(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate
• InChIKey: WKPWGQKGSOKKOO-RSFHAFMBSA-N
• INCHI: 1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11+/t19-,20+,25+,26-,27+,30+,33+,34+/m1/s1
• Isomeric SMILES: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)\C)OC)(NC(=O)O2)O
• Molecular Weight: 692.2

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Macrolactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Macrolactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolactams
• Alternative Parents: Alpha amino acid esters Alanine and derivatives Anisoles Alkyl aryl ethers 1,3-oxazinanes Aryl chlorides Tertiary carboxylic acid amides Acetamides Carbamate esters Organic carbonic acids and derivatives Lactams Carboxylic acid esters Azacyclic compounds Monocarboxylic acids and derivatives Oxacyclic compounds Alkanolamines Dialkyl ethers Epoxides Carbonyl compounds Hydrocarbon derivatives Organopnictogen compounds Organic oxides Organochlorides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Macrolactam - Alpha-amino acid ester - Alanine or derivatives - Alpha-amino acid or derivatives - Anisole - Alkyl aryl ether - 1,3-oxazinane - Oxazinane - Benzenoid - Aryl halide - Aryl chloride - Carbamic acid ester - Tertiary carboxylic acid amide - Acetamide - Lactam - Carboxamide group - Carboxylic acid ester - Carbonic acid derivative - Alkanolamine - Oxacycle - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Monocarboxylic acid or derivatives - Organopnictogen compound - Carbonyl group - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Organonitrogen compound - Organochloride - Organic oxygen compound - Organohalogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
• External Descriptors: Macrolides and lactone polyketides

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)

A-375 (9258 Activities)

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CCRF-CEM (65223 Activities)

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MCF7 (126967 Activities)

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OVCAR-3 (48710 Activities)

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SK-BR-3 (5175 Activities)

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A549 (127892 Activities)

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A-431 (6446 Activities)

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HEK293 (82097 Activities)

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KB (17409 Activities)

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SW-620 (52400 Activities)

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HCT-15 (51914 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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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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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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L1210 (27553 Activities)

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P388 (20296 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (144.47 mM; Need ultrasonic)
• Molecular Weight: 692.200 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 691.287 Da
• Monoisotopic Mass: 691.287 Da
• Topological Polar Surface Area: 156.000 Ų
• Heavy Atom Count: 48
• Formal Charge: 0
• Complexity: 1300.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1