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Compound Detail

CHEMBL292702

MAYTANSINE
🧪 Phase II
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🧪 Phase II
COc1cc2cc(c1Cl)N(C)C(=O)C[C@H](OC(=O)[C@H](C)N(C)C(C)=O)[C@]1(C)O[C@H]1[C@H](C)[C@@H]1C[C@@](O)(NC(=O)O1)[C@H](OC)/C=C/C=C(\C)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL292702
Name MAYTANSINE
Phase Phase II
Structure Type MOL
InChI Key WKPWGQKGSOKKOO-RSFHAFMBSA-N

Known Names

Maitansina Maitansine Maytansine NSC-153858
12
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
4
Known Names

Molecular Properties

692.2
MW (Da)
3.53
ALogP
10
HBA
2
HBD
156.5
PSA (Ų)
0.35
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -tansine
USAN Year 1978

Extended Properties

Molecular Formula C34H46ClN3O10
MW 692.21
Aromatic Rings 1
Heavy Atoms 48
NP-Likeness 2.42

Activity Summary

IC50 13 meas. best 10.52
Kd 1 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SK-BR-3
CHEMBL613834
 IC50 10.52 10.52 0.0 1
KB
CHEMBL398
 IC50 10.47 10.47 0.0 1
A-375
CHEMBL613859
 IC50 10.43 10.43 0.0 1
A-431
CHEMBL614069
 IC50 10.4 10.4 0.0 1
MCF7
CHEMBL387
 IC50 10.36 10.36 0.0 1
OVCAR-3
CHEMBL614213
 IC50 10.0 10.0 0.1 1
A549
CHEMBL392
 IC50 9.8 9.515 0.2 2
HeLa
CHEMBL399
 IC50 9.48 9.22 0.3 2
A2780
CHEMBL614004
 IC50 9.13 9.13 0.7 1
HCT-15
CHEMBL612263
 IC50 9.12 9.12 0.8 1
Tubulin
CHEMBL2095182
 Kd 7.85 7.85 14.0 1
Unchecked
CHEMBL612545
 IC50 7.72 7.72 19.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SK-BR-3 IC50 = 0.03 nM 10.52 Cytotoxicity against human SK-Br-3 cell line by clonogenic plating efficiency as... 16821799
KB IC50 = 0.034 nM 10.47 Cytotoxicity against human KB cell line by clonogenic plating efficiency assay a... 16821799
A-375 IC50 = 0.037 nM 10.43 Cytotoxicity against human A375 cell line by clonogenic plating efficiency assay... 16821799
A-431 IC50 = 0.04 nM 10.4 Cytotoxicity against human A431 cell line by clonogenic plating efficiency assay... 16821799
MCF7 IC50 = 0.044 nM 10.36 Cytotoxicity against human MCF7 cell line by clonogenic plating efficiency assay... 16821799
OVCAR-3 IC50 = 0.1 nM 10.0 Cytotoxicity against human Ovcar3 cell line by clonogenic plating efficiency ass... 16821799
A549 IC50 = 0.16 nM 9.8 Cytotoxicity against human A549 cell line by clonogenic plating efficiency assay... 16821799
HeLa IC50 = 0.33 nM 9.48 Antiproliferative activity against human HeLa cells assessed as inhibition of ce... 38294341
A549 IC50 = 0.59 nM 9.23 Antiproliferative activity against human A549 cells assessed as inhibition of ce... 38294341
A2780 IC50 = 0.74 nM 9.13 Antiproliferative activity against human A2780 cells assessed as inhibition of c... 38294341
HCT-15 IC50 = 0.75 nM 9.12 Cytotoxicity against human HCT15 cell line by clonogenic plating efficiency assa... 16821799
HeLa IC50 = 1.1 nM 8.96 Antiproliferative activity against human HeLa cells expressing tubulin betaIII a... 38294341
Tubulin Kd = 14.0 nM 7.85 Displacement of fluorescent Maytansine probe from tubulin (unknown origin) asses... 39068862
Unchecked IC50 = 19.0 nM 7.72 Antiproliferative activity against human A2780AD cells overexpressing P-gp asses... 38294341

Literature References

PubMed DOI Target Context # Activities
563462 10.1021/jm00199a006 Mus musculus 18
563462 10.1021/jm00199a006 P388 9
8277312 10.1021/np50100a011 NON-PROTEIN TARGET 8
38294341 10.1021/acs.jmedchem.3c01775 Unchecked 3
38294341 10.1021/acs.jmedchem.3c01775 HeLa 2
16821799 10.1021/jm060319f SK-BR-3 1
563462 10.1021/jm00199a006 KB 1
563462 10.1021/jm00199a006 Tubulin 1
39068862 10.1016/j.ejmech.2024.116709 Tubulin 1
1710653 10.1021/np50073a012 Human immunodeficiency virus type 1 reverse transcriptase 1
16821799 10.1021/jm060319f KB 1
2362268 10.1021/jm00169a014 No relevant target 1
16821799 10.1021/jm060319f A-431 1
16821799 10.1021/jm060319f A549 1
16821799 10.1021/jm060319f OVCAR-3 1
16821799 10.1021/jm060319f SW-620 1
16821799 10.1021/jm060319f HCT-15 1
16821799 10.1021/jm060319f MCF7 1
16821799 10.1021/jm060319f A-375 1
2362268 10.1021/jm00169a014 CCRF-CEM 1

Data from ChEMBL 36 via Core Engine