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Compound Detail

CHEMBL324162

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C=CCN(C)CCCCCCOc1ccc(C(=O)c2ccc(Br)cc2)c(F)c1.O=C(O)/C=C/C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL324162
Phase Preclinical
Structure Type MOL
InChI Key XCYAYLWZCRGKDS-WLHGVMLRSA-N
Parent Compound CHEMBL304858
Active Moiety CHEMBL304858
11
Targets
16
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

448.4
MW (Da)
5.88
ALogP
3
HBA
0
HBD
29.5
PSA (Ų)
0.23
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H31BrFNO6
MW 564.45
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -1.13

Activity Summary

IC50 16 meas. best 8.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lanosterol synthase
CHEMBL3593
 IC50 8.24 7.7333 5.7 3
Lanosterol synthase ERG7
CHEMBL5355
 IC50 6.68 6.68 210.0 1
Unchecked
CHEMBL612545
 IC50 6.47 6.26 340.0 2
Cycloartenol synthase
CHEMBL5356
 IC50 5.76 5.76 1750.0 1
KB
CHEMBL398
 IC50 5.54 5.54 2880.0 1
HeLa
CHEMBL399
 IC50 5.54 5.54 2890.0 1
Caco-2
CHEMBL614058
 IC50 5.52 5.52 2990.0 1
ADMET
CHEMBL612558
 IC50 5.42 5.42 3800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.28 5.1833 5260.0 3
MCF7
CHEMBL387
 IC50 5.17 5.17 6770.0 1
A549
CHEMBL392
 IC50 4.95 4.95 11300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lanosterol synthase IC50 = 5.7 nM 8.24 Inhibition of human liver microsome 2,3-OSC after 1 hr by Silica gel plate phosp... 22533316
Lanosterol synthase IC50 = 6.5 nM 8.19 In vitro inhibition of human 2,3-oxidosqualene cyclase. 12852766
Lanosterol synthase IC50 = 170.0 nM 6.77 Inhibition of human OSC expressed in Saccharomyces cerevisiae SMY8 19119009
Lanosterol synthase ERG7 IC50 = 210.0 nM 6.68 Inhibition of yeast OSC expressed in Saccharomyces cerevisiae SMY8 19119009
Unchecked IC50 = 340.0 nM 6.47 Inhibition of Pneumocystis carinii OSC expressed in Saccharomyces cerevisiae SMY... 19119009
Unchecked IC50 = 900.0 nM 6.05 Inhibition of Trypanosoma cruzi OSC expressed in Saccharomyces cerevisiae SMY8 19119009
Cycloartenol synthase IC50 = 1750.0 nM 5.76 Inhibition of Arabidopsis thaliana cycloartenol synthase expressed in Saccharomy... 19119009
KB IC50 = 2880.0 nM 5.54 Cytotoxicity against human KB cells after 72 hrs by MTT assay 22533316
HeLa IC50 = 2890.0 nM 5.54 Cytotoxicity against human HeLa cells after 72 hrs by MTT assay 22533316
Caco-2 IC50 = 2990.0 nM 5.52 Cytotoxicity against human Caco2 cells after 72 hrs by MTT assay 22533316
ADMET IC50 = 3800.0 nM 5.42 Cytotoxicity against human HCEC cells assessed as reduction in cell survival aft... 22533316
NON-PROTEIN TARGET IC50 = 5260.0 nM 5.28 Cytotoxicity against human LNZ308 cells after 72 hrs by MTT assay 22533316
NON-PROTEIN TARGET IC50 = 6100.0 nM 5.21 Cytotoxicity against human LN18 cells assessed as reduction in cell survival aft... 22533316
MCF7 IC50 = 6770.0 nM 5.17 Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay 22533316
NON-PROTEIN TARGET IC50 = 8800.0 nM 5.06 Cytotoxicity against human LN229 cells assessed as reduction in cell survival af... 22533316
A549 IC50 = 11300.0 nM 4.95 Cytotoxicity against human A549 cells after 72 hrs by MTT assay 22533316

Literature References

PubMed DOI Target Context # Activities
19119009 10.1016/j.bmcl.2008.12.040 Unchecked 22
22533316 10.1021/jm300256z NON-PROTEIN TARGET 8
22533316 10.1021/jm300256z ADMET 6
12852766 10.1021/jm021120f Lanosterol synthase 4
22533316 10.1021/jm300256z No relevant target 3
22533316 10.1021/jm300256z LN-18 3
22533316 10.1021/jm300256z LN-229 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
12852766 10.1021/jm021120f Cricetinae gen. sp. 2
19119009 10.1016/j.bmcl.2008.12.040 Cycloartenol synthase 1
19119009 10.1016/j.bmcl.2008.12.040 Lanosterol synthase ERG7 1
19119009 10.1016/j.bmcl.2008.12.040 Lanosterol synthase 1
22533316 10.1021/jm300256z OVCAR 1
22533316 10.1021/jm300256z MCF7 1
22533316 10.1021/jm300256z LNCaP 1
22533316 10.1021/jm300256z KB 1
22533316 10.1021/jm300256z HeLa 1
22533316 10.1021/jm300256z Caco-2 1
22533316 10.1021/jm300256z A549 1
22533316 10.1021/jm300256z Lanosterol synthase 1

Data from ChEMBL 36 via Core Engine