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Compound Detail

CHEMBL404116

LATRUNCULIN A
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C/C1=C/C(=O)O[C@@H]2C[C@@H](CC[C@H](C)/C=C\C=C\CC1)O[C@@](O)([C@@H]1CSC(=O)N1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL404116
Name LATRUNCULIN A
Phase Preclinical
Structure Type MOL
InChI Key DDVBPZROPPMBLW-IZGXTMSKSA-N
6
Targets
10
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

421.6
MW (Da)
3.86
ALogP
6
HBA
2
HBD
84.9
PSA (Ų)
0.63
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 C22H31NO5S
MW 421.56
Aromatic Rings 0
Heavy Atoms 29
NP-Likeness 3.14

Activity Summary

IC50 8 meas. best 6.55
Kd 2 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 6.77 6.735 170.0 2
Unchecked
CHEMBL612545
 IC50 6.55 6.55 284.0 1
MCF7
CHEMBL387
 IC50 6.32 6.32 480.0 1
HCT-116
CHEMBL394
 IC50 5.96 5.96 1100.0 1
MDA-MB-435
CHEMBL614697
 IC50 5.55 5.55 2800.0 1
MDA-MB-231
CHEMBL400
 IC50 5.38 5.38 4190.0 1
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha
CHEMBL2221345
 IC50 5.17 4.885 6700.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 170.0 nM 6.77 Binding affinity to rabbit skeletal muscle monomeric actin by isothermal calorim... 16372404
Unchecked Kd = 200.0 nM 6.7 Inhibition of actin polymerization 16372404
Unchecked IC50 = 284.0 nM 6.55 Inhibition of actin (unknown origin) polymerization incubated for 20 mins in pre... 33940466
MCF7 IC50 = 480.0 nM 6.32 Anticancer activity against human MCF7 cells assessed as inhibition of cell grow... 33940466
HCT-116 IC50 = 1100.0 nM 5.96 Cytotoxicity against human HCT116 cells after 3 days by trypan blue assay 18942825
MDA-MB-435 IC50 = 2800.0 nM 5.55 Cytotoxicity against human MDA-MB-435 cells 48 hrs by SRB assay 18942825
MDA-MB-231 IC50 = 4190.0 nM 5.38 Anticancer activity against human MDA-MB-231 cells assessed as inhibition of cel... 33940466
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha IC50 = 6700.0 nM 5.17 Inhibition of hypoxia-induced HIF1 activation in human T47D cells by cell based ... 18298079
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha IC50 = 25000.0 nM 4.6 Inhibition of 1,10-phenanthroline-induced HIF1 activation in human T47D cells by... 18298079

Literature References

PubMed DOI Target Context # Activities
18298079 10.1021/np070587w NON-PROTEIN TARGET 7
33940466 10.1016/j.ejmech.2021.113491 Unchecked 3
18298079 10.1021/np070587w Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha 2
16372404 10.1038/nchembio748 Unchecked 2
18622389 10.1038/nchembio.100 Saccharomyces cerevisiae 2
18942825 10.1021/jm8008585 MDA-MB-435 2
22129061 10.1021/np200673b HeLa 2
27161875 10.1016/j.bmc.2016.04.049 Unchecked 2
30904782 10.1016/j.ejmech.2019.03.024 NIH3T3 2
8350092 10.1021/np50096a015 A549 2
17897956 10.1074/jbc.m706923200 Proto-oncogene tyrosine-protein kinase LCK 2
8350092 10.1021/np50096a015 NON-PROTEIN TARGET 1
8350092 10.1021/np50096a015 Mus musculus 1
- 10.1021/np50082a019 P388 1
- 10.1021/np50082a019 Candida albicans 1
- 10.1021/np50082a019 Unchecked 1
15217296 10.1021/np0340753 A10 1
8350092 10.1021/np50096a015 HT-29 1
18942825 10.1021/jm8008585 A10 1
19800245 10.1016/j.bmc.2009.09.012 Saccharomyces cerevisiae 1

Data from ChEMBL 36 via Core Engine