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Compound Detail

CHEMBL221630

DEHYDROISO-ALPHA-LAPACHONE
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C=C(C)C1CC2=C(O1)C(=O)c1ccccc1C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL221630
Name DEHYDROISO-ALPHA-LAPACHONE
Phase Preclinical
Structure Type MOL
InChI Key ZDMOREUAQLXRCQ-UHFFFAOYSA-N
9
Targets
13
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

240.3
MW (Da)
2.68
ALogP
3
HBA
0
HBD
43.4
PSA (Ų)
0.71
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H12O3
MW 240.26
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 1.83

Activity Summary

IC50 13 meas. best 7.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DU-145
CHEMBL613508
 IC50 7.93 7.93 11.7 1
MCF7
CHEMBL387
 IC50 5.92 5.92 1200.0 1
HL-60
CHEMBL383
 IC50 5.84 5.84 1460.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.58 5.41 2600.0 2
1A9
CHEMBL614075
 IC50 5.58 5.565 2600.0 2
KB
CHEMBL398
 IC50 5.5 5.45 3200.0 3
HOS
CHEMBL614736
 IC50 5.4 5.4 4000.0 1
HaCaT
CHEMBL614392
 IC50 5.37 5.37 4300.0 1
A549
CHEMBL392
 IC50 5.19 5.19 6400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DU-145 IC50 = 11.67 nM 7.93 Anticancer activity against human DU145 cells after 72 hrs by XTT assay 18829316
MCF7 IC50 = 1200.0 nM 5.92 Cytotoxicity against human MCF7 cells after 3 days by SRB assay 15217280
HL-60 IC50 = 1460.0 nM 5.84 Cytotoxicity against human promyelocytic leukemia HL60 cell line by MTT assay 17249647
1A9 IC50 = 2600.0 nM 5.58 Cytotoxicity against human 1A9 cells after 3 days by SRB assay 15217280
NON-PROTEIN TARGET IC50 = 2600.0 nM 5.58 Cytotoxicity against human U87MG cells after 3 days by SRB assay 15217280
1A9 IC50 = 2800.0 nM 5.55 Cytotoxicity against paclitaxel-resistant human 1A9 cells after 3 days by SRB as... 15217280
KB IC50 = 3200.0 nM 5.5 Cytotoxicity against camptothecin-resistant human KB cells after 3 days by SRB a... 15217280
KB IC50 = 3500.0 nM 5.46 Cytotoxicity against etoposide-resistant human KB cells after 3 days by SRB assa... 15217280
HOS IC50 = 4000.0 nM 5.4 Cytotoxicity against human HOS cells after 3 days by SRB assay 15217280
KB IC50 = 4100.0 nM 5.39 Cytotoxicity against human KB cells after 3 days by SRB assay 15217280
HaCaT IC50 = 4300.0 nM 5.37 Antiproliferative activity against human HaCaT cells 10479319
NON-PROTEIN TARGET IC50 = 5700.0 nM 5.24 Cytotoxicity against vincristine-resistant human KBVIN cells after 3 days by SRB... 15217280
A549 IC50 = 6400.0 nM 5.19 Cytotoxicity against human A549 cells after 3 days by SRB assay 15217280

Literature References

PubMed DOI Target Context # Activities
10785421 10.1021/np990528l NON-PROTEIN TARGET 4
15217280 10.1021/np030450f KB 3
15217280 10.1021/np030450f NON-PROTEIN TARGET 2
- 10.1007/s00044-011-9788-9 Mycobacterium tuberculosis 2
10479319 10.1021/np990139r HaCaT 2
18829316 10.1016/j.bmcl.2008.09.053 DU-145 2
15217280 10.1021/np030450f CAKI-1 2
15217280 10.1021/np030450f 1A9 2
10785421 10.1021/np990528l M109 1
10785421 10.1021/np990528l SK-N-SH 1
17249647 10.1021/jm060849b HL-60 1
15217280 10.1021/np030450f A549 1
10785421 10.1021/np990528l SW626 1
15217280 10.1021/np030450f MCF7 1
15217280 10.1021/np030450f HOS 1
10785421 10.1021/np990528l LNCaP 1
10785421 10.1021/np990528l KB 1
10785421 10.1021/np990528l Col2 1
20304655 10.1016/j.bmc.2010.02.032 A2780 1
33333397 10.1016/j.ejmech.2020.113084 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine