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Compound Detail

CHEMBL4470997

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CC(C)=CCc1ccc(/C=C/C(=O)O)cc1NC(=O)CCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4470997
Phase Preclinical
Structure Type MOL
InChI Key SMYHHZFAWOLAAX-RVDMUPIBSA-N
4
Targets
12
Activities
1
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

363.5
MW (Da)
4.86
ALogP
2
HBA
2
HBD
66.4
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H25NO3
MW 363.46
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.38

Activity Summary

IC50 12 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HL-60
CHEMBL383
 IC50 8.0 7.525 10.0 2
THP-1
CHEMBL614245
 IC50 7.52 7.26 30.0 2
Aldo-keto reductase family 1 member C3
CHEMBL4681
 IC50 7.2 6.67 63.1 6
Aldo-keto reductase family 1 member C2
CHEMBL5847
 IC50 5.14 5.12 7200.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HL-60 IC50 = 10.0 nM 8.0 Potentiation of daunorubicin-induced cytotoxicity against human HL60 cells asses... 30836001
THP-1 IC50 = 30.0 nM 7.52 Potentiation of daunorubicin-induced cytotoxicity against human THP1 cells asses... 30836001
Aldo-keto reductase family 1 member C3 IC50 = 63.1 nM 7.2 Inhibition of recombinant AKR1C3 (unknown origin) assessed as reduction in S-tet... 27563402
Aldo-keto reductase family 1 member C3 IC50 = 66.0 nM 7.18 Inhibition of recombinant human AKR1C3 expressed in Escherichia coli BL21 (D3) u... 30836001
Aldo-keto reductase family 1 member C3 IC50 = 66.0 nM 7.18 Inhibition of recombinant human AKR1C3 expressed in Escherichia coli BL21 measur... 30836001
HL-60 IC50 = 90.0 nM 7.05 Potentiation of AraC-induced cytotoxicity against human HL60 cells assessed as A... 30836001
THP-1 IC50 = 100.0 nM 7.0 Potentiation of AraC-induced cytotoxicity against human THP1 cells assessed as A... 30836001
Aldo-keto reductase family 1 member C3 IC50 = 270.0 nM 6.57 Inhibition of AKR1C3 in human HL60 cells assessed as potentiation of etoposide-i... 27563402
Aldo-keto reductase family 1 member C3 IC50 = 530.0 nM 6.28 Inhibition of AKR1C3 in human HL60 cells assessed as potentiation of etoposide-i... 27563402
Aldo-keto reductase family 1 member C3 IC50 = 2470.0 nM 5.61 Inhibition of AKR1C3 in human KG1a cells assessed as potentiation of etoposide-i... 27563402
Aldo-keto reductase family 1 member C2 IC50 = 7200.0 nM 5.14 Inhibition of recombinant human AKR1C2 expressed in Escherichia coli BL21 (D3) u... 30836001
Aldo-keto reductase family 1 member C2 IC50 = 7943.28 nM 5.1 Inhibition of recombinant AKR1C2 (unknown origin) assessed as reduction in S-tet... 27563402

Literature References

PubMed DOI Target Context # Activities
27563402 10.1021/acsmedchemlett.6b00163 Aldo-keto reductase family 1 member C3 14
30836001 10.1021/acs.jmedchem.9b00090 HL-60 9
30836001 10.1021/acs.jmedchem.9b00090 KG-1a 9
30836001 10.1021/acs.jmedchem.9b00090 THP-1 9
27563402 10.1021/acsmedchemlett.6b00163 HL-60 4
30836001 10.1021/acs.jmedchem.9b00090 Aldo-keto reductase family 1 member C3 2
27563402 10.1021/acsmedchemlett.6b00163 KG-1a 2
30836001 10.1021/acs.jmedchem.9b00090 Aldo-keto reductase family 1 member C2 1
30836001 10.1021/acs.jmedchem.9b00090 Unchecked 1
27563402 10.1021/acsmedchemlett.6b00163 Aldo-keto reductase family 1 member C2 1
27563402 10.1021/acsmedchemlett.6b00163 Unchecked 1

Data from ChEMBL 36 via Core Engine