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Compound Detail

CHEMBL228286

(-)-ANTOFINE
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COc1ccc2c3c(c4cc(OC)c(OC)cc4c2c1)C[C@H]1CCCN1C3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL228286
Name (-)-ANTOFINE
Phase Preclinical
Structure Type MOL
InChI Key NCVWJDISIZHFQS-CQSZACIVSA-N
14
Targets
40
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

363.5
MW (Da)
4.54
ALogP
4
HBA
0
HBD
30.9
PSA (Ų)
0.64
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H25NO3
MW 363.46
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.42

Activity Summary

IC50 40 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 8.22 8.1067 6.0 3
MDA-MB-231
CHEMBL400
 IC50 8.22 8.07 6.0 2
CAKI-1
CHEMBL614067
 IC50 8.21 8.21 6.2 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.2 7.8686 6.3 7
Unchecked
CHEMBL612545
 IC50 8.14 7.3525 7.3 4
A549
CHEMBL392
 IC50 8.1 7.554 8.0 10
ZR-75-1
CHEMBL614393
 IC50 8.1 8.1 8.0 1
SK-HEP1
CHEMBL614912
 IC50 8.1 8.1 8.0 1
DU-145
CHEMBL613508
 IC50 8.05 7.7125 9.0 4
HT-1080
CHEMBL614580
 IC50 8.02 8.02 9.6 1
SNU-638
CHEMBL614935
 IC50 8.0 8.0 10.0 1
PC-3
CHEMBL390
 IC50 7.91 7.91 12.3 1
KB
CHEMBL398
 IC50 7.89 7.59 13.0 3
HCT-15
CHEMBL612263
 IC50 7.89 7.89 13.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 6.03 nM 8.22 Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 h... 26393416
MDA-MB-231 IC50 = 6.04 nM 8.22 Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after ... 26393416
CAKI-1 IC50 = 6.23 nM 8.21 Cytotoxicity against human Caki1 cells assessed as growth inhibition after 72 hr... 26393416
NON-PROTEIN TARGET IC50 = 6.32 nM 8.2 Cytotoxicity against human SKHEP1 cells assessed as growth inhibition after 72 h... 26393416
Unchecked IC50 = 7.3 nM 8.14 Inhibition of NF-kappaB-mediated transcription in human HepG cells 18077159
A549 IC50 = 8.0 nM 8.1 Cytotoxicity against human A549 cells by SRB microtiter plate assay 17585747
ZR-75-1 IC50 = 8.0 nM 8.1 Cytotoxicity against human ZR751cells by SRB microtiter plate assay 17585747
HCT-116 IC50 = 8.0 nM 8.1 Cytotoxicity against human HCT116 cells after 72 hrs by SRB assay 23294831
SK-HEP1 IC50 = 8.0 nM 8.1 Cytotoxicity against human SKHEP1 cells after 72 hrs by SRB assay 23294831
A549 IC50 = 8.52 nM 8.07 Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs... 26393416
NON-PROTEIN TARGET IC50 = 9.0 nM 8.05 Cytotoxicity against multidrug resistant human KB-Vin cells by SRB microtiter pl... 17585747
DU-145 IC50 = 9.0 nM 8.05 Cytotoxicity against human DU145 cells by SRB microtiter plate assay 17585747
HT-1080 IC50 = 9.6 nM 8.02 Cytotoxicity against human HT1080 cells by SRB assay 17049857
HCT-116 IC50 = 9.9 nM 8.0 Cytotoxicity against human HCT116 cells by SRB assay 17049857
SNU-638 IC50 = 10.0 nM 8.0 Cytotoxicity against human SNU638 cells after 72 hrs by SRB assay 23294831
A549 IC50 = 10.0 nM 8.0 Antiproliferative activity against human A549 cells after 72 hrs by ATPlite assa... 25499434
A549 IC50 = 10.4 nM 7.98 Cytotoxicity against human A549 cells by SRB assay 17049857
NON-PROTEIN TARGET IC50 = 10.38 nM 7.98 Cytotoxicity against human SNU638 cells assessed as growth inhibition after 72 h... 26393416
A549 IC50 = 11.0 nM 7.96 Cytotoxicity against human A549 cells after 72 hrs by SRB assay 23294831
MDA-MB-231 IC50 = 12.0 nM 7.92 Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay 28431881

Literature References

PubMed DOI Target Context # Activities
18077159 10.1016/j.bmcl.2007.11.054 Unchecked 11
23035814 10.1021/jf303550a Tobacco mosaic virus 8
23320928 10.1021/jf304905k Tobacco mosaic virus 8
21668000 10.1021/jm200330s Molecular identity unknown 6
16190646 10.1021/jf051050w Tobacco mosaic virus 2
23294831 10.1016/j.bmc.2012.11.039 A549 2
26393416 10.1021/acs.jmedchem.5b00764 NON-PROTEIN TARGET 2
23294831 10.1016/j.bmc.2012.11.039 No relevant target 2
12350151 10.1021/np0106384 NON-PROTEIN TARGET 2
18077159 10.1016/j.bmcl.2007.11.054 PANC-1 1
21668000 10.1021/jm200330s A549 1
19645447 10.1021/jm9009263 DU-145 1
19645447 10.1021/jm9009263 KB 1
18077159 10.1016/j.bmcl.2007.11.054 CCRF-CEM 1
17822295 10.1021/np0702077 Tobacco mosaic virus 1
17049857 10.1016/j.bmcl.2006.09.080 A549 1
17049857 10.1016/j.bmcl.2006.09.080 HCT-116 1
17585747 10.1021/jm061366a NON-PROTEIN TARGET 1
35033884 10.1016/j.bmc.2022.116614 A549 1
17585747 10.1021/jm061366a DU-145 1

Data from ChEMBL 36 via Core Engine