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Compound Detail

CHEMBL563939

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C=C1C(=O)O[C@H]2[C@H]1CC/C(CO)=C\CC[C@@]1(C)O[C@@H]21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL563939
Phase Preclinical
Structure Type MOL
InChI Key BAURYGOYSLZFPX-OOCKOLEWSA-N
21
Targets
27
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

264.3
MW (Da)
1.73
ALogP
4
HBA
1
HBD
59.1
PSA (Ų)
0.34
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 C15H20O4
MW 264.32
Aromatic Rings 0
Heavy Atoms 19
NP-Likeness 3.76

Activity Summary

IC50 24 meas. best 5.8
EC50 3 meas. best 4.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
T-cell
CHEMBL614309
 IC50 5.8 5.8 1590.0 1
FHC
CHEMBL614654
 IC50 5.55 5.55 2810.0 1
MDA-MB-231
CHEMBL400
 IC50 5.42 5.2967 3840.0 3
HCT-116
CHEMBL394
 IC50 5.31 5.215 4930.0 2
SW480
CHEMBL612544
 IC50 5.23 5.23 5870.0 1
4T1
CHEMBL612589
 IC50 5.23 5.23 5880.0 1
U-87 MG
CHEMBL614247
 IC50 5.2 5.2 6280.0 1
MCF7
CHEMBL387
 IC50 5.17 5.17 6760.0 1
KG-1a
CHEMBL4296453
 IC50 5.17 5.17 6800.0 1
HT-29
CHEMBL384
 IC50 5.16 5.16 6950.0 1
A549
CHEMBL392
 IC50 5.13 5.065 7490.0 2
SUM-159-PT
CHEMBL4483269
 IC50 5.13 5.13 7450.0 1
HL-60
CHEMBL383
 IC50 4.99 4.99 10300.0 1
Bel-7402
CHEMBL614279
 IC50 4.98 4.98 10500.0 1
U2OS
CHEMBL615023
 IC50 4.97 4.97 10700.0 1
PANC-1
CHEMBL614139
 IC50 4.96 4.96 10860.0 1
HepG2
CHEMBL395
 IC50 4.92 4.92 11970.0 1
NIH3T3
CHEMBL614822
 IC50 4.92 4.92 12000.0 1
Unchecked
CHEMBL612545
 EC50 4.85 4.735 14000.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.81 4.81 15500.0 1
MDA-MB-468
CHEMBL614335
 IC50 4.7 4.7 19970.0 1
Unchecked
CHEMBL612545
 IC50 4.63 4.63 23170.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 868.3 umol/l.min Mus musculus
CL 0.07 L/min Mus musculus
Cmax 4500.0 nM Mus musculus
F 6.7 % Mus musculus
T1/2 1.03 hr Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
T-cell IC50 = 1590.0 nM 5.8 Antiproliferative activity against concanavalin A-stimulated C57BL/6 mouse T cel... 38718622
FHC IC50 = 2810.0 nM 5.55 Cytotoxicity against human FHC cells 30006167
MDA-MB-231 IC50 = 3840.0 nM 5.42 Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition... 38104376
HCT-116 IC50 = 4930.0 nM 5.31 Antiproliferative activity against human HCT116 cells after 72 hrs by MTT assay 30006167
MDA-MB-231 IC50 = 5590.0 nM 5.25 Antiproliferative activity against human MDA-MB-231 cells measured after 72 hrs ... 30739826
SW480 IC50 = 5870.0 nM 5.23 Cytotoxicity against human SW480 cells assessed as reduction in cell viability i... 34847663
4T1 IC50 = 5880.0 nM 5.23 Antiproliferative activity against mouse 4T1 cells assessed as inhibition of cel... 38104376
MDA-MB-231 IC50 = 6010.0 nM 5.22 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 34847663
U-87 MG IC50 = 6280.0 nM 5.2 Antiproliferative activity against human U87 cells after 72 hrs by MTT assay 30006167
KG-1a IC50 = 6800.0 nM 5.17 Cytotoxicity against human KG1a cells assessed as decrease in cell proliferation... 28068601
MCF7 IC50 = 6760.0 nM 5.17 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 38104376
HT-29 IC50 = 6950.0 nM 5.16 Cytotoxicity against human HT-29 cells assessed as reduction in cell viability i... 34847663
SUM-159-PT IC50 = 7450.0 nM 5.13 Antiproliferative activity against human SUM159 cells assessed as inhibition of ... 38104376
A549 IC50 = 7490.0 nM 5.13 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 34847663
HCT-116 IC50 = 7500.0 nM 5.12 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 34847663
A549 IC50 = 9940.0 nM 5.0 Antiproliferative activity against human A549 cells after 72 hrs by MTT assay 30006167
HL-60 IC50 = 10300.0 nM 4.99 Cytotoxicity against human HL60 cells assessed as decrease in cell proliferation... 28068601
Bel-7402 IC50 = 10500.0 nM 4.98 Antiproliferative activity against human Bel7402 cells after 72 hrs by MTT assay 30006167
U2OS IC50 = 10700.0 nM 4.97 Cytotoxicity against human U2OS cells assessed as reduction in cell viability in... 34847663
PANC-1 IC50 = 10860.0 nM 4.96 Antiproliferative activity against human PANC1 cells after 72 hrs by MTT assay 30006167

Literature References

PubMed DOI Target Context # Activities
28049618 10.1016/j.bmc.2016.12.036 ADMET 6
30006167 10.1016/j.ejmech.2018.06.058 HCT-116 5
30121494 10.1016/j.ejmech.2018.08.010 Unchecked 3
30006167 10.1016/j.ejmech.2018.06.058 Unchecked 3
28049618 10.1016/j.bmc.2016.12.036 NON-PROTEIN TARGET 2
38718622 10.1016/j.ejmech.2024.116426 Pyruvate kinase PKM 1
19505822 10.1016/j.bmcl.2009.05.092 NON-PROTEIN TARGET 1
34847663 10.1021/acs.jmedchem.1c01380 A549 1
34847663 10.1021/acs.jmedchem.1c01380 HCT-116 1
34847663 10.1021/acs.jmedchem.1c01380 SW480 1
34847663 10.1021/acs.jmedchem.1c01380 HT-29 1
30739826 10.1016/j.ejmech.2019.01.058 MDA-MB-231 1
30006167 10.1016/j.ejmech.2018.06.058 NIH3T3 1
30006167 10.1016/j.ejmech.2018.06.058 FHC 1
30006167 10.1016/j.ejmech.2018.06.058 U-87 MG 1
30006167 10.1016/j.ejmech.2018.06.058 A549 1
30006167 10.1016/j.ejmech.2018.06.058 PANC-1 1
30006167 10.1016/j.ejmech.2018.06.058 Bel-7402 1
28525840 10.1016/j.ejmech.2017.05.031 Unchecked 1
28068601 10.1016/j.ejmech.2016.12.044 KG-1a 1

Data from ChEMBL 36 via Core Engine