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Compound Detail

CHEMBL1237054

PLICAMYCIN
💊 Approved Drug
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💊 Approved Drug
CO[C@H](C(=O)[C@@H](O)[C@@H](C)O)[C@@H]1Cc2cc3cc(O[C@H]4C[C@@H](O[C@@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@H](O)[C@@H](C)O4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@H]1C[C@@H](O[C@@H]2C[C@@H](O)[C@@H](O[C@@H]3C[C@](C)(O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@H](O)[C@@H](C)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1237054
Name PLICAMYCIN
Phase Approved
Structure Type MOL
InChI Key XDKMHMINQXATOR-RCFLUEAHSA-N
Therapeutic ✓ Yes

Known Names

A-2371 ANTIBIOTIC LA-7017 Aureolic acid LA-7017 Mithracin Mithramycin Mithramycin a NSC-24559 PA-144 Plicamicina Plicamycin Plicamycine
7
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
12
Known Names
3
Indications
1
Mechanisms

Molecular Properties

1085.2
MW (Da)

Drug Information

Molecule Type Small molecule
First Approval 1970
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -mycin
USAN Year 1965

Extended Properties

Molecular Formula C52H76O24
MW 1085.16

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Neoplasms Sarcoma Sarcoma, Ewing

ATC Classification

L01DC02
plicamycin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 12 meas. best 7.9
EC50 5 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.9 7.86 12.5 2
HT-29
CHEMBL384
 IC50 7.48 7.0333 33.0 3
P388
CHEMBL389
 EC50 7.3 7.3 50.0 1
P388
CHEMBL389
 IC50 7.22 7.06 60.0 3
A549
CHEMBL392
 EC50 7.22 7.22 60.0 1
HT-29
CHEMBL384
 EC50 7.16 7.16 70.0 1
A549
CHEMBL392
 IC50 6.7 6.7 200.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL2146315
 EC50 6.5 6.5 320.0 1
Plasmodium berghei
CHEMBL612653
 IC50 6.08 6.08 833.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
 EC50 4.8 4.8 15800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 12.5 nM 7.9 HARVARD: Inhibition of blood stage Plasmodium falciparum Dd2 infection 22586124
Plasmodium falciparum IC50 = 15.0 nM 7.82 HARVARD: Inhibition of blood stage Plasmodium falciparum 3D7 infection 22586124
HT-29 IC50 = 33.0 nM 7.48 Antiproliferative activity against human HT-29 cells after 96 hrs by MTT assay 2778449
P388 EC50 = 50.0 nM 7.3 Cytotoxicity against mouse P388 cells by MTT assay 24529868
A549 EC50 = 60.0 nM 7.22 Cytotoxicity against human A549 cells by MTT assay 24529868
P388 IC50 = 60.0 nM 7.22 Cytotoxicity against mouse P388 cells after 3 days by MTT assay 16643054
HT-29 EC50 = 70.0 nM 7.16 Cytotoxicity against human HT-29 cells by MTT assay 24529868
HT-29 IC50 = 80.0 nM 7.1 Cytotoxicity against human HT29 cells after 6 days by MTT assay 16643054
P388 IC50 = 100.0 nM 7.0 Cytotoxicity against mouse P388 cells 15387641
P388 IC50 = 111.0 nM 6.96 Antiproliferative activity against mouse P388 cells after 48 hrs by MTT assay 2778449
A549 IC50 = 200.0 nM 6.7 Cytotoxicity against human A549 cells 15387641
HT-29 IC50 = 300.0 nM 6.52 Cytotoxicity against human HT29 cells 15387641
Nuclear receptor subfamily 1 group I member 2 EC50 = 320.0 nM 6.5 Activation of rat PXR expressed in human HepG2 cells after 24 hrs by luciferase ... 20966043
Plasmodium berghei IC50 = 833.0 nM 6.08 HARVARD: Inhibition of liver stage Plasmodium berghei infection in HepG2 cells 22586124
Nuclear receptor subfamily 1 group I member 2 EC50 = 15800.0 nM 4.8 Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay 20966043

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
10560743 10.1016/s0960-894x(99)00547-8 K562 6
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 6
2778449 10.1021/np50063a010 P388 4
2778449 10.1021/np50063a010 HT-29 4
22578073 10.1021/jm300234t Mus musculus 4
20014752 10.1021/tx900326k Hepatotoxicity 3
22578073 10.1021/jm300234t Plasma 3
21807523 10.1016/j.bmc.2011.07.013 NIH3T3 2
22931300 10.1021/tx300075j Liver microsomes 2
22586124 10.1073/pnas.1118370109 Plasmodium falciparum 2
18571290 10.1016/j.ejmech.2008.05.001 K562 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
19072686 10.1021/jm800982q K562 1
15387641 10.1021/np0400858 P388 1
8594142 10.1021/np50125a002 P388 1
20966043 10.1124/dmd.110.035105 ADMET 1
18197601 10.1021/np0705763 MDA-MB-231 1
3746824 10.1021/jm00159a041 Homo sapiens 1

Data from ChEMBL 36 via Core Engine