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Compound Detail

CHEMBL3039217

TRIPTOPHENOLIDE
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CC(C)c1ccc2c(c1O)CC[C@H]1C3=C(CC[C@]21C)C(=O)OC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3039217
Name TRIPTOPHENOLIDE
Phase Preclinical
Structure Type MOL
InChI Key KPXIBWGPZSPABK-FXAWDEMLSA-N
7
Targets
9
Activities
1
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

312.4
MW (Da)
3.98
ALogP
3
HBA
1
HBD
46.5
PSA (Ų)
0.80
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 C20H24O3
MW 312.41
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 2.41

Activity Summary

IC50 9 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 IC50 6.58 6.4367 260.0 3
Unchecked
CHEMBL612545
 IC50 6.36 6.36 437.0 1
Androgen receptor
CHEMBL3072
 IC50 6.33 6.33 467.0 1
HepG2
CHEMBL395
 IC50 4.77 4.77 17010.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.65 4.65 22210.0 1
Bcap37
CHEMBL613842
 IC50 4.65 4.65 22400.0 1
A549
CHEMBL392
 IC50 4.37 4.37 42880.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor IC50 = 260.0 nM 6.58 Antagonist activity at wild type AR in human PC3 cells assessed as suppression o... 27994731
Androgen receptor IC50 = 388.0 nM 6.41 Antagonist activity at AR T877A mutant (unknown origin) transfected in human PC3... 27994731
Unchecked IC50 = 437.0 nM 6.36 Antagonist activity at AR W741C/T877A double mutant (unknown origin) transfected... 27994731
Androgen receptor IC50 = 467.0 nM 6.33 Displacement of fluormone-DHT green from His/GST-tagged rat AR ligand binding do... 27994731
Androgen receptor IC50 = 480.0 nM 6.32 Antagonist activity at AR F876L mutant (unknown origin) expressed in human PC3 c... 27994731
HepG2 IC50 = 17010.0 nM 4.77 Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay 27133593
NON-PROTEIN TARGET IC50 = 22210.0 nM 4.65 Cytotoxicity against human Hep3B cells after 48 hrs by MTT assay 27133593
Bcap37 IC50 = 22400.0 nM 4.65 Cytotoxicity against human Bcap37 cells after 48 hrs by MTT assay 27133593
A549 IC50 = 42880.0 nM 4.37 Cytotoxicity against human A549 cells after 48 hrs by MTT assay 27133593

Literature References

PubMed DOI Target Context # Activities
27994731 10.1021/acsmedchemlett.6b00180 Androgen receptor 18
27994731 10.1021/acsmedchemlett.6b00180 Unchecked 3
27994731 10.1021/acsmedchemlett.6b00180 NON-PROTEIN TARGET 2
38964974 10.1016/j.bmc.2024.117788 A2780 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
29153424 10.1016/j.bmcl.2017.11.014 Pseudomonas fluorescens 1
29153424 10.1016/j.bmcl.2017.11.014 Escherichia coli 1
29153424 10.1016/j.bmcl.2017.11.014 Bacillus subtilis 1
29153424 10.1016/j.bmcl.2017.11.014 Staphylococcus aureus 1
28011223 10.1016/j.bmcl.2016.12.032 A549 1
28011223 10.1016/j.bmcl.2016.12.032 PC-3 1
28011223 10.1016/j.bmcl.2016.12.032 SK-OV-3 1
27133593 10.1016/j.bmcl.2016.04.026 A549 1
27133593 10.1016/j.bmcl.2016.04.026 MCF7 1
27133593 10.1016/j.bmcl.2016.04.026 U-251 1
27133593 10.1016/j.bmcl.2016.04.026 HepG2 1
27133593 10.1016/j.bmcl.2016.04.026 Bcap37 1
27133593 10.1016/j.bmcl.2016.04.026 NON-PROTEIN TARGET 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1

Data from ChEMBL 36 via Core Engine