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Compound Detail

CHEMBL15192

LAPACHONE
🧪 Phase II
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🧪 Phase II
CC1(C)CCC2=C(O1)c1ccccc1C(=O)C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL15192
Name LAPACHONE
Phase Phase II
Structure Type MOL
InChI Key QZPQTZZNNJUOLS-UHFFFAOYSA-N

Known Names

.beta.-lapachone Arq 501 ARQ-501 Beta lapachone Beta-lap-wj Beta-lapachone Lapachone Lapachone, beta- MB-12066 NSC-26326 NSC-629749
47
Targets
137
Activities
3
Assay Types
4
PK Parameters
20
Publications
11
Known Names
3
Indications

Molecular Properties

242.3
MW (Da)
2.75
ALogP
3
HBA
0
HBD
43.4
PSA (Ų)
0.66
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C15H14O3
MW 242.27
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 1.52

Indications

Neoplasms Neoplasms Carcinoma

Activity Summary

IC50 129 meas. best 8.13
Ki 5 meas. best 7.0
EC50 3 meas. best 5.95

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DU-145
CHEMBL613508
 IC50 8.13 8.13 7.4 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 7.0 7.0 100.0 2
Cocaine esterase
CHEMBL3180
 Ki 6.96 6.96 109.0 1
Thiosulfate sulfurtransferase
CHEMBL4295835
 IC50 6.92 6.92 120.0 1
MDA-MB-435
CHEMBL614697
 IC50 6.6 6.6 250.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.6 5.9325 250.0 16
HL-60
CHEMBL383
 IC50 6.57 5.942 270.0 5
LoVo
CHEMBL614721
 IC50 6.52 6.52 300.0 1
Leptomonas seymouri
CHEMBL612917
 IC50 6.4 6.4 400.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 6.36 6.216 440.0 5
RAW264.7
CHEMBL612557
 IC50 6.33 5.86 470.0 2
MCF7
CHEMBL387
 IC50 6.3 6.1833 500.0 3
GroEL/GroES
CHEMBL4106139
 IC50 6.23 6.06 590.0 2
SK-MEL-28
CHEMBL614919
 IC50 6.22 6.22 600.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 6.21 6.21 610.0 1
Leishmania infantum
CHEMBL612848
 IC50 6.17 6.06 670.0 2
HaCaT
CHEMBL614392
 IC50 6.16 6.0775 700.0 4
MOLT-4
CHEMBL614177
 IC50 6.11 6.11 780.0 1
1A9
CHEMBL614075
 IC50 6.1 6.1 800.0 1
A549
CHEMBL392
 IC50 6.1 5.3327 800.0 15
HCT-8
CHEMBL613510
 IC50 6.08 6.08 830.0 2
HCT-116
CHEMBL394
 IC50 6.06 6.035 870.0 2
SF-295
CHEMBL614908
 IC50 6.04 6.035 910.0 4
Tyrosyl-DNA phosphodiesterase 2
CHEMBL2169736
 IC50 6.01 6.01 970.0 1
KB
CHEMBL398
 IC50 6.0 5.89 1000.0 3
PC-3
CHEMBL390
 EC50 5.95 5.95 1130.0 1
OVCAR-8
CHEMBL612555
 IC50 5.94 5.94 1160.0 2
Mucosa-associated lymphoid tissue lymphoma translocation protein 1
CHEMBL3632452
 IC50 5.92 5.82 1200.0 2
Liver carboxylesterase 1
CHEMBL2265
 Ki 5.91 5.91 1220.0 1
Leishmania amazonensis
CHEMBL612877
 IC50 5.86 5.7 1390.0 2
MDA-MB-231
CHEMBL400
 IC50 5.86 5.6967 1390.0 3
HOS
CHEMBL614736
 IC50 5.85 5.85 1400.0 1
K562
CHEMBL385
 IC50 5.8 5.8 1600.0 1
PC-3
CHEMBL390
 IC50 5.78 5.78 1650.0 1
PC-3M
CHEMBL4296484
 IC50 5.74 5.74 1820.0 1
A549/TR
CHEMBL4483226
 IC50 5.72 5.34 1900.0 2
OVCAR-3
CHEMBL614213
 IC50 5.72 5.72 1900.0 1
HSP60/HSP10
CHEMBL4106131
 IC50 5.68 5.68 2100.0 1
PBMC
CHEMBL613107
 IC50 5.68 5.68 2100.0 1
HepG2
CHEMBL395
 IC50 5.55 5.55 2830.0 1
Lysine-specific demethylase 4E
CHEMBL1293226
 IC50 5.52 5.52 3000.0 2
NAD(P)H dehydrogenase [quinone] 1
CHEMBL3623
 IC50 5.52 5.495 3000.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.5 5.0988 3162.3 8
Lysine-specific demethylase 4E
CHEMBL1293226
 Ki 5.45 5.45 3550.0 1
Nuclear factor NF-kappa-B complex
CHEMBL2094258
 IC50 5.4 5.4 4000.0 1
A549
CHEMBL392
 EC50 5.38 5.38 4210.0 1
L02
CHEMBL4296457
 IC50 5.34 5.0933 4540.0 3
NCI-H596
CHEMBL612256
 IC50 5.3 4.8367 5060.0 3
MCF7
CHEMBL387
 EC50 5.0 5.0 9960.0 1
NADPH--cytochrome P450 reductase
CHEMBL2169731
 IC50 4.96 4.96 11000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 114.0 L/hr/m2 Homo sapiens
F 15.5 % Homo sapiens
T1/2 0.4 hr Mus musculus
T1/2 2.45 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DU-145 IC50 = 7.4 nM 8.13 Anticancer activity against human DU145 cells after 72 hrs by XTT assay 18829316
Indoleamine 2,3-dioxygenase 1 Ki = 100.0 nM 7.0 Noncompetitive inhibition of human recombinant IDO1 expressed in Escherichia col... 25970480
Indoleamine 2,3-dioxygenase 1 Ki = 100.0 nM 7.0 Inhibition of IDO1 (unknown origin) 33215494
Cocaine esterase Ki = 109.0 nM 6.96 Inhibition of human intestinal CES2 expressed in baculovirus infected sf9 cells ... 28112927
Thiosulfate sulfurtransferase IC50 = 120.0 nM 6.92 Inhibition of native rhodanese (unknown origin) assessed as reduction in rhodane... 30852084
MDA-MB-435 IC50 = 250.0 nM 6.6 Cytotoxicity against human MDA-MB-435 cells after 72 hrs by MTT assay 19947600
MDA-MB-435 IC50 = 250.0 nM 6.6 Cytotoxicity against human MDA-MB-435 cells after 72 hrs by MTT assay 21115213
MDA-MB-435 IC50 = 250.0 nM 6.6 Cytotoxicity against human MDA-MB-435 cells assessed as cell viability after 72 ... 26142490
NON-PROTEIN TARGET IC50 = 250.0 nM 6.6 Cytotoxicity against human MDA-MB-435 cells overexpressing NQO1 assessed as redu... 27341379
HL-60 IC50 = 270.0 nM 6.57 Cytotoxicity against human promyelocytic leukemia HL60 cell line by MTT assay 17249647
NON-PROTEIN TARGET IC50 = 300.0 nM 6.52 Antiproliferative activity against apoptosis sensitive mouse B16F10 cells after ... 26883150
LoVo IC50 = 300.0 nM 6.52 Antiproliferative activity against human LoVo cells after 72 hrs by MTT assay 26883150
NON-PROTEIN TARGET IC50 = 400.0 nM 6.4 Antiproliferative activity against apoptosis sensitive human Hs683 cells after 7... 26883150
Leptomonas seymouri IC50 = 400.0 nM 6.4 Antitrypanosomal activity against Leptomonas seymouri 18276039
NON-PROTEIN TARGET IC50 = 400.0 nM 6.4 Antiproliferative activity against apoptosis resistant human U373 cells after 72... 26883150
Indoleamine 2,3-dioxygenase 1 IC50 = 440.0 nM 6.36 Inhibition of purified human recombinant IDO1 expressed in Escherichia coli asse... 31525930
Indoleamine 2,3-dioxygenase 1 IC50 = 440.0 nM 6.36 Inhibition of human recombinant IDO1 expressed in Escherichia coli 33341650
Indoleamine 2,3-dioxygenase 1 IC50 = 440.0 nM 6.36 Inhibition of recombinant human IDO1 expressed in Escherichia coli assessed as r... 32055299
RAW264.7 IC50 = 470.0 nM 6.33 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 23232148
MCF7 IC50 = 500.0 nM 6.3 Antiproliferative activity against apoptosis sensitive human MCF7 cells after 72... 26883150

Literature References

PubMed DOI Target Context # Activities
35436747 10.1016/j.bmc.2022.116749 Nakaseomyces glabratus 32
30003778 10.1021/acs.jnatprod.8b00247 MDA-MB-231 30
17609380 10.1073/pnas.0702176104 A549 19
35436747 10.1016/j.bmc.2022.116749 Saccharomyces cerevisiae 18
17609380 10.1073/pnas.0702176104 NCI-H596 14
35436747 10.1016/j.bmc.2022.116749 Unchecked 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
31525930 10.1021/acs.jmedchem.9b00942 Indoleamine 2,3-dioxygenase 1 7
23232148 10.1016/j.bmc.2012.10.047 RAW264.7 7
27341379 10.1016/j.ejmech.2016.06.019 NON-PROTEIN TARGET 7
19674905 10.1016/j.bmc.2009.07.039 Unchecked 5
17950604 10.1016/j.bmcl.2007.10.005 Human gammaherpesvirus 4 5
26883150 10.1016/j.bmcl.2016.02.015 NON-PROTEIN TARGET 5
33158575 10.1016/j.ejmech.2020.112962 ADMET 5
21115213 10.1016/j.ejmech.2010.11.006 HL-60 5
21115213 10.1016/j.ejmech.2010.11.006 MDA-MB-435 5
21115213 10.1016/j.ejmech.2010.11.006 HCT-8 5
30508483 10.1021/acs.jmedchem.8b01424 NAD(P)H dehydrogenase [quinone] 1 5
6205152 10.1021/jm00374a010 Gallus gallus 5
21115213 10.1016/j.ejmech.2010.11.006 SF-295 5

Data from ChEMBL 36 via Core Engine