Structure Database (LMSD)

Common Name
Maytansine
Systematic Name
Synonyms
LM ID
LMPK04000017
Formula
C34H46N3O10Cl
Exact Mass
Calculate m/z
691.287175
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Macrolides and lactone polyketides [PK04]

Biological Context

Maytansine is an ansa macrolide originally isolated from M. serrata that has anticancer activity.1 It inhibits the growth of L1210, L-5178-Y, and P388 murine leukemia cells (EC50s = 0.6, 12, and 1.5 nM, respectively). Maytansine (20 µM) inhibits erythrocyte and brain tubulin polymerization.2 In vivo, maytansine (0.025-0.1 mg/kg) increases survival in a P388 murine leukemia model.1 It has also been used in the synthesis of cytotoxic payload moieties of antibody-drug conjugates (ADCs).3

This information has been provided by Cayman Chemical

References

1. Wolpert-Defilippes, M.K., Adamson, R.H., Cysyk, R.L., et al. Initial studies on the cytotoxic action of maytansine, a novel ansa macrolide. Biochem. Pharmacol. 24(6), 751-754 (1975).
2. Luduena, R.F., Anderson, W.H., Prasad, V., et al. Interactions of vinblastine and maytansine with tubulin. Ann. N. Y. Acad. Sci. 466, 718-732 (1986).
3. Yaghoubi, S., Karimi, M.H., Lotfinia, M., et al. Potential drugs used in the antibody-drug conjugate (ADC) architecture for cancer therapy. J. Cell Physiol. 235(1), 31-64 (2020).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Maytenus (#123430)
Magnoliopsida (#3398)
Maytansine, a novel antileukemic ansa macrolide from Maytenus ovatus.,
J Am Chem Soc, 1972
Pubmed ID: 5062169

String Representations

InChiKey (Click to copy)
WKPWGQKGSOKKOO-RSFHAFMBSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@@]12(C)O[C@@]1([H])[C@H](C)[C@@]1([H])OC(N[C@@](O)([C@H](OC)C=CC=C(C)CC3=CC(OC)=C(Cl)C(=C3)N(C)C(=O)C[C@@H]2OC(=O)[C@H](C)N(C)C(=O)C)C1)=O

Other Databases

Wikipedia
Maytansine
KEGG ID
C10606
CHEBI ID
6701
PubChem CID
5281828
Cayman ID
36062
PDB ID
3GT

Calculated Physicochemical Properties

Heavy Atoms 48
Rings 4
Aromatic Rings 1
Rotatable Bonds 6
Van der Waals Molecular Volume 648.77
Topological Polar Surface Area 158.54
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 13
logP 5.54
Molar Refractivity 180.21

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Created at
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Updated at
12th Dec 2023