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Compound Detail

CHEMBL2437258

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COC(=O)CNC(=O)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2437258
Phase Preclinical
Structure Type MOL
InChI Key KQRHXJLBAGJUFU-VZUCSPMQSA-N
8
Targets
10
Activities
3
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

391.4
MW (Da)
1.94
ALogP
7
HBA
2
HBD
111.2
PSA (Ų)
0.51
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H25NO7
MW 391.42
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness 1.11

Activity Summary

IC50 6 meas. best 7.04
EC50 2 meas. best 8.16
Ki 2 meas. best 6.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PBMC
CHEMBL613107
 EC50 8.16 8.16 6.9 1
PBMC
CHEMBL613107
 IC50 7.04 7.04 92.0 1
Inosine-5'-monophosphate dehydrogenase 2
CHEMBL2002
 Ki 6.31 6.31 487.0 1
Inosine-5'-monophosphate dehydrogenase 1
CHEMBL1822
 Ki 6.28 6.28 522.0 1
DU-145
CHEMBL613508
 IC50 5.51 5.51 3100.0 1
K562
CHEMBL385
 IC50 4.8 4.8 16000.0 1
HL-60
CHEMBL383
 IC50 4.66 4.66 22000.0 1
Jurkat
CHEMBL397
 EC50 4.61 4.61 24580.0 1
Jurkat
CHEMBL397
 IC50 4.18 4.18 65280.0 1
PC-3
CHEMBL390
 IC50 4.1 4.1 79000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PBMC EC50 = 6.9 nM 8.16 Antiproliferative activity against human PBMC assessed as incorporation of [3H]t... 24121309
PBMC IC50 = 92.0 nM 7.04 Cytotoxicity against human PBMC after 72 hrs by MTT assay 24121309
Inosine-5'-monophosphate dehydrogenase 2 Ki = 487.0 nM 6.31 Inhibition of IMPDH2 (unknown origin) 24269162
Inosine-5'-monophosphate dehydrogenase 1 Ki = 522.0 nM 6.28 Inhibition of IMPDH1 (unknown origin) 24269162
DU-145 IC50 = 3100.0 nM 5.51 Antiproliferative activity against human DU145 cells 24269162
K562 IC50 = 16000.0 nM 4.8 Antiproliferative activity against human K562 cells 24269162
HL-60 IC50 = 22000.0 nM 4.66 Antiproliferative activity against human HL60 cells 24269162
Jurkat EC50 = 24580.0 nM 4.61 Antiproliferative activity against human Jurkat cells assessed as incorporation ... 24121309
Jurkat IC50 = 65280.0 nM 4.18 Cytotoxicity against human Jurkat cells after 48 hrs by MTT assay 24121309
PC-3 IC50 = 79000.0 nM 4.1 Antiproliferative activity against human PC3 cells 24269162

Literature References

PubMed DOI Target Context # Activities
24121309 10.1016/j.ejmech.2013.09.026 PBMC 3
24121309 10.1016/j.ejmech.2013.09.026 Jurkat 3
24121309 10.1016/j.ejmech.2013.09.026 Unchecked 1
24269162 10.1016/j.bmcl.2013.11.005 PC-3 1
24269162 10.1016/j.bmcl.2013.11.005 DU-145 1
24269162 10.1016/j.bmcl.2013.11.005 HL-60 1
24269162 10.1016/j.bmcl.2013.11.005 K562 1
24269162 10.1016/j.bmcl.2013.11.005 Inosine-5'-monophosphate dehydrogenase 2 1
24269162 10.1016/j.bmcl.2013.11.005 Inosine-5'-monophosphate dehydrogenase 1 1

Data from ChEMBL 36 via Core Engine