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Compound Detail

CHEMBL441441

ALPHA-LAPACHONE
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CC1(C)CCC2=C(O1)C(=O)c1ccccc1C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL441441
Name ALPHA-LAPACHONE
Phase Preclinical
Structure Type MOL
InChI Key PJWHOPKRRBUSDH-UHFFFAOYSA-N
21
Targets
27
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

242.3
MW (Da)
2.91
ALogP
3
HBA
0
HBD
43.4
PSA (Ų)
0.70
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H14O3
MW 242.27
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 1.55

Activity Summary

IC50 27 meas. best 6.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
 IC50 6.68 6.09 210.0 2
P388
CHEMBL389
 IC50 6.1 6.1 800.0 1
Leptomonas seymouri
CHEMBL612917
 IC50 5.39 5.39 4100.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 5.36 5.36 4340.0 1
Leishmania infantum
CHEMBL612848
 IC50 5.23 5.045 5850.0 2
SK-MEL-2
CHEMBL614917
 IC50 5.1 5.1 7900.0 1
HL-60
CHEMBL383
 IC50 5.09 4.98 8180.0 2
HaCaT
CHEMBL614392
 IC50 5.0 5.0 10000.0 1
SW626
CHEMBL1075593
 IC50 4.91 4.91 12400.0 1
OVCAR-8
CHEMBL612555
 IC50 4.83 4.83 14790.0 1
Leishmania amazonensis
CHEMBL612877
 IC50 4.82 4.805 15150.0 2
Plasmodium falciparum
CHEMBL364
 IC50 4.8 4.8 15800.0 1
SF-295
CHEMBL614908
 IC50 4.73 4.73 18770.0 1
HCT-116
CHEMBL394
 IC50 4.72 4.72 19110.0 1
Lu1
CHEMBL613290
 IC50 4.66 4.66 21900.0 1
Crithidia fasciculata
CHEMBL612650
 IC50 4.57 4.57 27000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.56 4.52 27700.0 3
LNCaP
CHEMBL612518
 IC50 4.53 4.53 29300.0 1
MCF7
CHEMBL387
 IC50 4.42 4.42 38000.0 1
Col2
CHEMBL614462
 IC50 4.39 4.39 40900.0 1
KB
CHEMBL398
 IC50 4.27 4.27 53700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 210.0 nM 6.68 Growth inhibition of Trypanosoma cruzi Tulahuen epimastigotes assessed as drug l... 18029184
P388 IC50 = 800.0 nM 6.1 Cytotoxicity against mouse P388 cells after 72 hrs by SRB assay 12088425
Trypanosoma cruzi IC50 = 3190.0 nM 5.5 Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes after 72 hrs... 22795899
Leptomonas seymouri IC50 = 4100.0 nM 5.39 Antitrypanosomal activity against Leptomonas seymouri 18276039
Indoleamine 2,3-dioxygenase 1 IC50 = 4340.0 nM 5.36 Inhibition of purified human recombinant IDO 18318466
Leishmania infantum IC50 = 5850.0 nM 5.23 Antileishmanial activity against antimony-resistant Leishmania infantum MCAN/BR/... 23535320
SK-MEL-2 IC50 = 7900.0 nM 5.1 Cytotoxicity against human SK-MEL-2 cells after 72 hrs by SRB assay 12088425
HL-60 IC50 = 8180.0 nM 5.09 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay -
HaCaT IC50 = 10000.0 nM 5.0 Antiproliferative activity against human HaCaT cells 10479319
SW626 IC50 = 12400.0 nM 4.91 Cytotoxicity against human SW626 cells after 72 hrs by SRB assay 12088425
HL-60 IC50 = 13460.0 nM 4.87 Cytotoxicity against human promyelocytic leukemia HL60 cell line by MTT assay 17249647
Leishmania infantum IC50 = 13880.0 nM 4.86 Antileishmanial activity against antimony-sensitive Leishmania infantum MCAN/BR/... 23535320
OVCAR-8 IC50 = 14790.0 nM 4.83 Cytotoxicity against human OVCAR8 cells after 72 hrs by MTT assay -
Leishmania amazonensis IC50 = 15150.0 nM 4.82 Antileishmanial activity against antimony-resistant Leishmania amazonensis MHOM/... 23535320
Plasmodium falciparum IC50 = 15800.0 nM 4.8 Antimalarial activity against Plasmodium falciparum W2 incubated for 24 hrs 33333397
Leishmania amazonensis IC50 = 16080.0 nM 4.79 Antileishmanial activity against antimony-sensitive Leishmania amazonensis MHOM/... 23535320
SF-295 IC50 = 18770.0 nM 4.73 Cytotoxicity against human SF295 cells after 72 hrs by MTT assay -
HCT-116 IC50 = 19110.0 nM 4.72 Cytotoxicity against human HCT116 cells after 72 hrs by MTT assay -
Lu1 IC50 = 21900.0 nM 4.66 Cytotoxicity against human Lu1 cells after 72 hrs by SRB assay 12088425
Crithidia fasciculata IC50 = 27000.0 nM 4.57 Antitrypanosomal activity against Crithidia fasciculata 18276039

Literature References

PubMed DOI Target Context # Activities
35436747 10.1016/j.bmc.2022.116749 Saccharomyces cerevisiae 12
23535320 10.1016/j.ejmech.2013.02.038 Unchecked 4
18029184 10.1016/j.bmc.2007.10.038 Trypanosoma cruzi 4
10785421 10.1021/np990528l NON-PROTEIN TARGET 4
22819765 10.1016/j.bmcl.2012.06.073 NON-PROTEIN TARGET 4
12088425 10.1021/np010322w SW626 3
31378595 10.1016/j.bmc.2019.07.045 Unchecked 3
31378595 10.1016/j.bmc.2019.07.045 Mycobacterium tuberculosis 3
12088425 10.1021/np010322w NON-PROTEIN TARGET 2
22795899 10.1016/j.bmc.2012.06.027 Trypanosoma cruzi 2
18276039 10.1016/j.ejmech.2007.12.023 No relevant target 2
22819765 10.1016/j.bmcl.2012.06.073 Jurkat 2
23535320 10.1016/j.ejmech.2013.02.038 Leishmania infantum 2
32044231 10.1016/j.bmc.2020.115347 Signal transducer and activator of transcription 3 2
10479319 10.1021/np990139r HaCaT 2
23535320 10.1016/j.ejmech.2013.02.038 Leishmania amazonensis 2
10785421 10.1021/np990528l SK-N-SH 1
18378461 10.1016/j.bmc.2008.03.032 Trypanosoma cruzi 1
10785421 10.1021/np990528l M109 1
18318466 10.1021/jm7014155 Indoleamine 2,3-dioxygenase 1 1

Data from ChEMBL 36 via Core Engine