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Compound Detail

CHEMBL96926

THAPSIGARGIN
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C/C=C(/C)C(=O)O[C@H]1C(C)=C2[C@H]([C@@H]1OC(=O)CCCCCCC)[C@@](C)(OC(C)=O)C[C@H](OC(=O)CCC)[C@@]1(O)[C@H]2OC(=O)[C@@]1(C)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL96926
Name THAPSIGARGIN
Phase Preclinical
Structure Type MOL
InChI Key IXFPJGBNCFXKPI-FSIHEZPISA-N
669
Targets
698
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

650.8
MW (Da)
3.93
ALogP
12
HBA
2
HBD
172.0
PSA (Ų)
0.10
QED
2
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C34H50O12
MW 650.76
Aromatic Rings 0
Heavy Atoms 46
NP-Likeness 2.33

Activity Summary

IC50 694 meas. best 10.71
Kd 2 meas. best 9.7
Ki 2 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCCIT
CHEMBL1075511
 IC50 10.71 10.71 0.0 1
CGTH-W-1
CHEMBL2366300
 IC50 10.68 10.68 0.0 1
Capan-2
CHEMBL1075417
 IC50 10.66 10.66 0.0 1
MC116
CHEMBL2366256
 IC50 10.61 10.61 0.0 1
786-0
CHEMBL613102
 IC50 10.61 10.61 0.0 1
MES-SA
CHEMBL614343
 IC50 10.57 10.57 0.0 1
ES1
CHEMBL2366146
 IC50 10.44 10.44 0.0 1
A4-Fuk
CHEMBL2366356
 IC50 10.29 10.29 0.1 1
IGROV-1
CHEMBL613984
 IC50 10.22 10.22 0.1 1
PSN1
CHEMBL614241
 IC50 10.17 10.17 0.1 1
8505C
CHEMBL1075387
 IC50 10.12 10.12 0.1 1
NOS-1
CHEMBL2366141
 IC50 10.08 10.08 0.1 1
D283 Med
CHEMBL614476
 IC50 10.08 10.08 0.1 1
A-375
CHEMBL613859
 IC50 10.05 10.05 0.1 1
PANC-03-27
CHEMBL1075557
 IC50 10.04 10.04 0.1 1
KYSE-140
CHEMBL1075484
 IC50 10.03 10.03 0.1 1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
CHEMBL3136
 Ki 10.0 10.0 0.1 1
COLO-679
CHEMBL1075426
 IC50 9.96 9.96 0.1 1
NALM-6
CHEMBL614187
 IC50 9.95 9.95 0.1 1
HT-1080
CHEMBL614580
 IC50 9.95 9.95 0.1 1
KYSE-410
CHEMBL1075487
 IC50 9.92 9.92 0.1 1
CAL-12T
CHEMBL1075406
 IC50 9.89 9.89 0.1 1
HCC 2998
CHEMBL613855
 IC50 9.89 9.89 0.1 1
HGC-27
CHEMBL1075463
 IC50 9.88 9.88 0.1 1
ES4
CHEMBL2366118
 IC50 9.88 9.88 0.1 1
MCF7
CHEMBL387
 IC50 9.88 7.03 0.1 3
LCLC-97TM1
CHEMBL1075489
 IC50 9.86 9.86 0.1 1
BL-41
CHEMBL2366173
 IC50 9.85 9.85 0.1 1
ES6
CHEMBL2366373
 IC50 9.85 9.85 0.1 1
NY
CHEMBL1075552
 IC50 9.84 9.84 0.1 1
SW1710
CHEMBL1075590
 IC50 9.82 9.82 0.1 1
MZ1-PC
CHEMBL2366204
 IC50 9.82 9.82 0.2 1
CAL-27
CHEMBL1075408
 IC50 9.77 9.77 0.2 1
Bos taurus
CHEMBL613489
 IC50 9.77 9.675 0.2 2
LCLC-103H cell line
CHEMBL614066
 IC50 9.76 9.76 0.2 1
KYSE-70 cell line
CHEMBL614012
 IC50 9.74 9.74 0.2 1
DMS-273
CHEMBL614034
 IC50 9.74 9.74 0.2 1
MEL-JUSO
CHEMBL1075501
 IC50 9.73 9.73 0.2 1
NCI-H520
CHEMBL614099
 IC50 9.72 9.72 0.2 1
A2780
CHEMBL614004
 IC50 9.71 9.71 0.2 1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
CHEMBL4693
 IC50 9.7 9.055 0.2 2
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
CHEMBL4693
 Kd 9.7 9.7 0.2 2
TGBC24TKB
CHEMBL2366093
 IC50 9.69 9.69 0.2 1
AN3-CA
CHEMBL1075392
 IC50 9.66 9.66 0.2 1
OPM-2
CHEMBL2366353
 IC50 9.66 9.66 0.2 1
SK-LMS-1
CHEMBL2366096
 IC50 9.65 9.65 0.2 1
KGN
CHEMBL2366154
 IC50 9.65 9.65 0.2 1
Huh-7
CHEMBL614039
 IC50 9.62 9.62 0.2 1
A 172
CHEMBL614512
 IC50 9.6 9.6 0.3 1
OVCAR-3
CHEMBL614213
 IC50 9.56 9.56 0.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCCIT IC50 = 0.01961 nM 10.71 SANGER: Inhibition of human NCCIT cell growth in a cell viability assay. -
CGTH-W-1 IC50 = 0.02088 nM 10.68 SANGER: Inhibition of human CGTH-W-1 cell growth in a cell viability assay. -
Capan-2 IC50 = 0.02163 nM 10.66 SANGER: Inhibition of human Capan-2 cell growth in a cell viability assay. -
786-0 IC50 = 0.02478 nM 10.61 SANGER: Inhibition of human 786-0 cell growth in a cell viability assay. -
MC116 IC50 = 0.02451 nM 10.61 SANGER: Inhibition of human MC116 cell growth in a cell viability assay. -
MES-SA IC50 = 0.02681 nM 10.57 SANGER: Inhibition of human MES-SA cell growth in a cell viability assay. -
ES1 IC50 = 0.03648 nM 10.44 SANGER: Inhibition of human ES1 cell growth in a cell viability assay. -
A4-Fuk IC50 = 0.05177 nM 10.29 SANGER: Inhibition of human A4-Fuk cell growth in a cell viability assay. -
IGROV-1 IC50 = 0.0607 nM 10.22 SANGER: Inhibition of human IGROV-1 cell growth in a cell viability assay. -
PSN1 IC50 = 0.06693 nM 10.17 SANGER: Inhibition of human PSN1 cell growth in a cell viability assay. -
8505C IC50 = 0.0762 nM 10.12 SANGER: Inhibition of human 8505C cell growth in a cell viability assay. -
D283 Med IC50 = 0.084 nM 10.08 SANGER: Inhibition of human D-283MED cell growth in a cell viability assay. -
NOS-1 IC50 = 0.08247 nM 10.08 SANGER: Inhibition of human NOS-1 cell growth in a cell viability assay. -
A-375 IC50 = 0.08921 nM 10.05 SANGER: Inhibition of human A375 cell growth in a cell viability assay. -
PANC-03-27 IC50 = 0.09108 nM 10.04 SANGER: Inhibition of human PANC-03-27 cell growth in a cell viability assay. -
KYSE-140 IC50 = 0.09243 nM 10.03 SANGER: Inhibition of human KYSE-140 cell growth in a cell viability assay. -
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 Ki = 0.1 nM 10.0 Inhibition of SERCA1a (unknown origin) ATPase activity 29292225
COLO-679 IC50 = 0.1093 nM 9.96 SANGER: Inhibition of human COLO-679 cell growth in a cell viability assay. -
NALM-6 IC50 = 0.1121 nM 9.95 SANGER: Inhibition of human NALM-6 cell growth in a cell viability assay. -
HT-1080 IC50 = 0.112 nM 9.95 SANGER: Inhibition of human HT-1080 cell growth in a cell viability assay. -

Literature References

PubMed DOI Target Context # Activities
29636219 10.1016/j.bmcl.2018.03.065 Unchecked 11
17698618 10.1128/aac.00582-07 Toxoplasma gondii 10
18391949 10.1038/nchembio.79 COS-7 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
22582991 10.1021/jm300515q HL-60 5
18024584 10.1073/pnas.0709695104 H4 4
20813948 10.1126/science.1193225 Plasmodium falciparum 4
22582991 10.1021/jm300515q CCRF-CEM 4
18256683 10.1038/leu.2008.9 J.gamma1 4
11741487 10.1021/jm010985a Unchecked 4
- 10.1584/jpestics.G08-29 Ryanodien receptor 3
18256683 10.1038/leu.2008.9 Jurkat 3
22582991 10.1021/jm300515q K562 3
- 10.1016/S0960-894X(01)80174-8 Bos taurus 2
17339374 10.1128/aac.01544-06 Trypanosoma brucei rhodesiense 2
26428873 10.1016/j.bmcl.2015.09.044 HeLa 2
17339374 10.1128/aac.01544-06 Trypanosoma cruzi 2
16124763 10.1021/np050115m Unchecked 2
25951057 10.1021/np500836y ADMET 2
30528127 10.1016/j.bmc.2018.11.011 Unchecked 2

Data from ChEMBL 36 via Core Engine