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Compound Detail

CHEMBL2333561

THAILANSTATIN A
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CC(=O)O[C@@H](C)/C=C\C(=O)N[C@@H]1C[C@H](C)[C@H](C/C=C(C)/C=C/[C@H]2O[C@H](CC(=O)O)C[C@@]3(CO3)[C@@H]2O)O[C@@H]1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2333561
Name THAILANSTATIN A
Phase Preclinical
Structure Type MOL
InChI Key GJKQDOMCDFJANR-FUDLAKRJSA-N
8
Targets
9
Activities
1
Assay Types
1
PK Parameters
16
Publications
0
Known Names

Molecular Properties

535.6
MW (Da)
2.45
ALogP
8
HBA
3
HBD
143.9
PSA (Ų)
0.17
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H41NO9
MW 535.63
Aromatic Rings 0
Heavy Atoms 38
NP-Likeness 2.57

Activity Summary

IC50 9 meas. best 7.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCI-N87
CHEMBL614197
 IC50 7.23 7.23 59.0 1
MDA-MB-468
CHEMBL614335
 IC50 6.85 6.85 142.0 1
BT-474
CHEMBL614529
 IC50 6.84 6.84 145.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.79 6.79 161.0 1
HEK-293T
CHEMBL3706568
 IC50 6.53 6.53 296.2 1
NCI-H1975
CHEMBL614348
 IC50 6.5 6.5 320.0 1
MES-SA
CHEMBL614343
 IC50 6.38 6.38 418.6 2
HEK293
CHEMBL614818
 IC50 6.19 6.19 650.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 78.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCI-N87 IC50 = 59.0 nM 7.23 Cytotoxicity against human NCI-N87 cells after 4 days by MTS/cell proliferation ... 25098528
MDA-MB-468 IC50 = 142.0 nM 6.85 Cytotoxicity against human MDA-MB-468 cells after 4 days by MTS/cell proliferati... 25098528
BT-474 IC50 = 145.0 nM 6.84 Cytotoxicity against human BT474 cells after 4 days by MTS/cell proliferation as... 25098528
NON-PROTEIN TARGET IC50 = 161.0 nM 6.79 Cytotoxicity against human MDA-MB-DYT2 cells after 4 days by MTS/cell proliferat... 25098528
HEK-293T IC50 = 296.2 nM 6.53 Cytotoxicity against HEK293T cells assessed as inhibition in cell growth 33974423
NCI-H1975 IC50 = 320.0 nM 6.5 Cytotoxicity against human NCI-H1975 cells after 4 days by MTS/cell proliferatio... 25098528
MES-SA IC50 = 418.6 nM 6.38 Cytotoxicity against human MES-SA cells assessed as inhibition in cell growth 33974423
MES-SA IC50 = 419.0 nM 6.38 Cytotoxicity against human MES-SA cells 39068862
HEK293 IC50 = 650.0 nM 6.19 Inhibition of Pre-mRNA splicing in human HEK293 cells using p32-labeled CDC14-15... 23517093

Literature References

PubMed DOI Target Context # Activities
23517093 10.1021/np300913h No relevant target 2
23517093 10.1021/np300913h SK-OV-3 1
23517093 10.1021/np300913h MDA-MB-231 1
23517093 10.1021/np300913h NON-PROTEIN TARGET 1
23517093 10.1021/np300913h DU-145 1
23517093 10.1021/np300913h HEK293 1
25098528 10.1021/np500342m No relevant target 1
25098528 10.1021/np500342m NCI-N87 1
25098528 10.1021/np500342m MDA-MB-468 1
25098528 10.1021/np500342m BT-474 1
25098528 10.1021/np500342m NON-PROTEIN TARGET 1
25098528 10.1021/np500342m NCI-H1975 1
33974423 10.1021/acs.jnatprod.1c00100 MES-SA/Dx5 1
33974423 10.1021/acs.jnatprod.1c00100 MES-SA 1
33974423 10.1021/acs.jnatprod.1c00100 HEK-293T 1
39068862 10.1016/j.ejmech.2024.116709 MES-SA 1

Data from ChEMBL 36 via Core Engine