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Compound Detail

CHEMBL435191

EDOTECARIN
🧪 Phase III
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🧪 Phase III
O=C1c2c(c3c4ccc(O)cc4n([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3c3[nH]c4cc(O)ccc4c23)C(=O)N1NC(CO)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL435191
Name EDOTECARIN
Phase Phase III
Structure Type MOL
InChI Key QMVPQBFHUJZJCS-NTKFZFFISA-N

Known Names

Edotecarin Edotecarina Edotecarine J-107088 PF-804950
10
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names
3
Indications
1
Mechanisms

Molecular Properties

608.6
MW (Da)
-0.73
ALogP
13
HBA
10
HBD
241.2
PSA (Ų)
0.11
QED
3
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -tecarin
USAN Year 2005

Extended Properties

Molecular Formula C29H28N4O11
MW 608.56
Aromatic Rings 5
Heavy Atoms 44
NP-Likeness 0.87

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA topoisomerase I inhibitor INHIBITOR DNA topoisomerase 1 ✓ ✓

Indications

Glioblastoma Breast Neoplasms Stomach Neoplasms

Activity Summary

IC50 10 meas. best 9.1
EC50 4 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.1 9.1 0.8 1
DNA topoisomerase 1
CHEMBL2814
 EC50 8.82 8.82 1.5 1
P388
CHEMBL389
 IC50 8.82 8.82 1.5 1
P388/S
CHEMBL614220
 IC50 8.32 8.32 4.8 1
MKN-45
CHEMBL614354
 IC50 8.32 7.74 4.8 2
A2780
CHEMBL614004
 IC50 8.19 8.19 6.5 1
DNA topoisomerase 1
CHEMBL1781
 EC50 7.29 7.1933 51.0 3
NCI-H460
CHEMBL396
 IC50 6.71 6.71 193.0 1
DLD-1
CHEMBL614285
 IC50 6.08 6.08 840.0 1
Unchecked
CHEMBL612545
 IC50 4.75 4.75 18000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 0.8 nM 9.1 Cytotoxicity against human GLC4 cells after 72 hrs by sulforhodamine B assay 22749423
DNA topoisomerase 1 EC50 = 1.5 nM 8.82 Inhibition of DNA topoisomerase 1 in mouse P388/S cells assessed as formation of... 19397324
P388 IC50 = 1.5 nM 8.82 The compound was tested for the cytotoxic activity against murine leukemia cells... 10743939
MKN-45 IC50 = 4.8 nM 8.32 Tested for cytotoxic activity against human stomach cancer cells (MKN-45) 10743939
P388/S IC50 = 4.8 nM 8.32 Cytotoxicity against mouse P388/S cells after 72 hrs by colorimetric tetrazolium... 19397324
A2780 IC50 = 6.5 nM 8.19 Cytotoxicity against human A2780 cells after 72 hrs by sulforhodamine B assay 22749423
DNA topoisomerase 1 EC50 = 51.0 nM 7.29 Inhibitory effect on topoisomerase-1 mediated DNA cleavage using supercoiled pBR... 10743939
DNA topoisomerase 1 EC50 = 51.0 nM 7.29 Inhibition of topoisomerase-1 (unknown origin) using pBR 322 DNA as substrate 27687971
MKN-45 IC50 = 70.0 nM 7.16 Cytotoxicity against human MKN45 cells after 72 hrs 19397324
DNA topoisomerase 1 EC50 = 100.0 nM 7.0 Inhibition of human DNA topoisomerase 1-mediated DNA cleavage assessed as relaxa... 19397324
NCI-H460 IC50 = 193.0 nM 6.71 Cytotoxicity against human NCI-H460 cells after 72 hrs by sulforhodamine B assay 22749423
DLD-1 IC50 = 840.0 nM 6.08 Cytotoxicity against human DLD1 cells after 72 hrs 19397324
Unchecked IC50 = 18000.0 nM 4.75 Inhibition of PKC 19397324

Literature References

PubMed DOI Target Context # Activities
10743939 10.1016/s0960-894x(00)00004-4 MKN-45 3
10743939 10.1016/s0960-894x(00)00004-4 P388 2
19397324 10.1021/jm801641t DNA topoisomerase 1 2
19397324 10.1021/jm801641t MKN-45 2
22749423 10.1016/j.bmcl.2012.06.016 A2780 2
19397324 10.1021/jm801641t Mus musculus 2
19397324 10.1021/jm801641t NON-PROTEIN TARGET 2
19397324 10.1021/jm801641t Unchecked 1
27687971 10.1016/j.bmc.2016.09.045 DNA topoisomerase 1 1
11306452 - Broad substrate specificity ATP-binding cassette transporter ABCG2 1
22749423 10.1016/j.bmcl.2012.06.016 Mus musculus 1
22749423 10.1016/j.bmcl.2012.06.016 NON-PROTEIN TARGET 1
22749423 10.1016/j.bmcl.2012.06.016 NCI-H460 1
19397324 10.1021/jm801641t MX1 1
19397324 10.1021/jm801641t Epidermal growth factor receptor 1
10743939 10.1016/s0960-894x(00)00004-4 DNA topoisomerase 1 1
19397324 10.1021/jm801641t DLD-1 1
19397324 10.1021/jm801641t P388/S 1
10743939 10.1016/s0960-894x(00)00004-4 Mus sp. 1
10743939 10.1016/s0960-894x(00)00004-4 Protein kinase C (PKC) 1

Data from ChEMBL 36 via Core Engine