Structure via PubChem · Public domain (PubChem)
maytansine
Sign in to saveAlso known as NSC-153858, NSC 153858
Maitansine (INN), or maytansine (USAN), is a cytotoxic agent. It inhibits the assembly of microtubules by binding to tubulin at the rhizoxin binding site. The maytansine binding site and binding mode has been characterized.
Chemical data
- Formula
- C34H46ClN3O10
- Molecular weight
- 692.2 g/mol
- 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
- 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
- InChIKey
- WKPWGQKGSOKKOO-RSFHAFMBSA-N
- XLogP
- 2
- Polar surface area
- 156 Ų
- H-bond donors
- 2
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,444 papers- Maytansine.Cancer treatment reviews · 1978
- Biomimetic Nanoerythrosome-Coated Aptamer-DNA Tetrahedron/Maytansine Conjugates: pH-Responsive and Targeted Cytotoxicity for HER2-Positive Breast Cancer.Advanced materials (Deerfield Beach, Fla.) · 2022
- New insights into the anticancer therapeutic potential of maytansine and its derivatives.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2023
- Strategies and challenges for the next generation of antibody-drug conjugates.Nature reviews. Drug discovery · 2017
- Bridging the maytansine and vinca sites: Cryptophycins target β-tubulin's T5-loop.The Journal of biological chemistry · 2024
via PubMed
Wikidata facts
- Mass
- 691.287
Show 6 more facts
- chemical formula
- C₃₄H₄₆ClN₃O₁₀
- canonical SMILES
- CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)C)C)C)OC)(NC(=O)O2)O
- found in taxon
- Gymnosporia emarginata
- 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
- World Health Organisation international non-proprietary name
- maitansine
- Commons category
- Maitansine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Maytansinoids
- See also
- References
Maitansine (INN), or maytansine (USAN), is a cytotoxic agent. It inhibits the assembly of microtubules by binding to tubulin at the rhizoxin binding site. The maytansine binding site and binding mode has been characterized.
It is a macrolide of the ansamycin type and can be isolated from plants of the genus Maytenus.
Excerpted from Wikipedia’s “maytansine” article, available under the CC BY-SA 4.0 licence.