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Compound Detail

CHEMBL511708

BACCHARIN
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CC(C)=CCc1cc(/C=C/C(=O)O)ccc1OC(=O)CCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL511708
Name BACCHARIN
Phase Preclinical
Structure Type MOL
InChI Key BJIVLGIZOMJQRT-GXDHUFHOSA-N
6
Targets
32
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

364.4
MW (Da)
4.83
ALogP
3
HBA
1
HBD
63.6
PSA (Ų)
0.32
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 C23H24O4
MW 364.44
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.81

Activity Summary

IC50 22 meas. best 7.7
Ki 10 meas. best 7.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
THP-1
CHEMBL614245
 IC50 7.7 7.2 20.0 2
Aldo-keto reductase family 1 member C3
CHEMBL4681
 Ki 7.34 6.767 46.0 10
HL-60
CHEMBL383
 IC50 7.16 7.16 70.0 1
Aldo-keto reductase family 1 member C3
CHEMBL4681
 IC50 7.0 6.3267 100.0 9
Aldo-keto reductase family 1 member C4
CHEMBL4999
 IC50 4.68 4.68 21000.0 1
Aldo-keto reductase family 1 member C2
CHEMBL5847
 IC50 4.3 4.295 50118.7 2
Unchecked
CHEMBL612545
 IC50 4.11 4.11 77400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
THP-1 IC50 = 20.0 nM 7.7 Potentiation of daunorubicin-induced cytotoxicity against human THP1 cells asses... 30836001
Aldo-keto reductase family 1 member C3 Ki = 46.0 nM 7.34 Competitive inhibition of human recombinant AKR1C3 Phe306Leu mutant expressed in... 22506594
Aldo-keto reductase family 1 member C3 Ki = 56.0 nM 7.25 Competitive inhibition of human recombinant AKR1C3 expressed in Escherichia coli... 22506594
Aldo-keto reductase family 1 member C3 Ki = 56.0 nM 7.25 Noncompetitive inhibition of human recombinant AKR1C3 expressed in Escherichia c... 22506594
Aldo-keto reductase family 1 member C3 Ki = 56.0 nM 7.25 Competitive inhibition of human recombinant AKR1C3 expressed in Escherichia coli... 22506594
HL-60 IC50 = 70.0 nM 7.16 Potentiation of AraC-induced cytotoxicity against human HL60 cells assessed as A... 30836001
Aldo-keto reductase family 1 member C3 IC50 = 100.0 nM 7.0 Inhibition of recombinant AKR1C3 (unknown origin) assessed as reduction in S-tet... 27563402
Aldo-keto reductase family 1 member C3 IC50 = 100.0 nM 7.0 Inhibition of recombinant human AKR1C3 expressed in Escherichia coli BL21 (D3) u... 30836001
Aldo-keto reductase family 1 member C3 Ki = 105.0 nM 6.98 Competitive inhibition of human recombinant AKR1C3 Ser129Ile mutant expressed in... 22506594
Aldo-keto reductase family 1 member C3 IC50 = 110.0 nM 6.96 Inhibition of AKR1C3 (unknown origin) assessed as dehydrogenase activity of enzy... 25182963
Aldo-keto reductase family 1 member C3 IC50 = 110.0 nM 6.96 Inhibition of recombinant human AKR1C3 expressed in Escherichia coli BL21 measur... 30836001
Aldo-keto reductase family 1 member C3 IC50 = 110.0 nM 6.96 Inhibition of human recombinant AKR1C3 expressed in Escherichia coli JM109 cells... 22506594
Aldo-keto reductase family 1 member C3 Ki = 148.0 nM 6.83 Competitive inhibition of human recombinant AKR1C3 Trp227Tyr mutant expressed in... 22506594
THP-1 IC50 = 200.0 nM 6.7 Potentiation of AraC-induced cytotoxicity against human THP1 cells assessed as A... 30836001
Aldo-keto reductase family 1 member C3 IC50 = 280.0 nM 6.55 Inhibition of AKR1C3 in human HL60 cells assessed as potentiation of etoposide-i... 27563402
Aldo-keto reductase family 1 member C3 Ki = 300.0 nM 6.52 Competitive inhibition of human recombinant AKR1C3 Gln222His mutant expressed in... 22506594
Aldo-keto reductase family 1 member C3 IC50 = 510.0 nM 6.29 Inhibition of AKR1C3 in human HL60 cells assessed as potentiation of etoposide-i... 27563402
Aldo-keto reductase family 1 member C3 Ki = 550.0 nM 6.26 Competitive inhibition of human recombinant AKR1C3 Met120Val mutant expressed in... 22506594
Aldo-keto reductase family 1 member C3 Ki = 850.0 nM 6.07 Competitive inhibition of human recombinant AKR1C3 Ser118Phe mutant expressed in... 22506594
Aldo-keto reductase family 1 member C3 Ki = 1200.0 nM 5.92 Competitive inhibition of human recombinant AKR1C3 Phe311Leu mutant expressed in... 22506594

Literature References

PubMed DOI Target Context # Activities
22506594 10.1021/np201002x Aldo-keto reductase family 1 member C3 15
30836001 10.1021/acs.jmedchem.9b00090 KG-1a 9
30836001 10.1021/acs.jmedchem.9b00090 THP-1 9
30836001 10.1021/acs.jmedchem.9b00090 HL-60 9
27563402 10.1021/acsmedchemlett.6b00163 Aldo-keto reductase family 1 member C3 9
21865046 10.1016/j.bmc.2011.07.060 HCT-116 5
30836001 10.1021/acs.jmedchem.9b00090 Unchecked 3
25182963 10.1016/j.bmc.2014.08.007 Unchecked 3
25182963 10.1016/j.bmc.2014.08.007 Aldo-keto reductase family 1 member C3 3
22506594 10.1021/np201002x Unchecked 3
22506594 10.1021/np201002x PC-3 3
21865046 10.1016/j.bmc.2011.07.060 Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha 3
34454129 10.1016/j.bmc.2021.116372 ADMET 2
30836001 10.1021/acs.jmedchem.9b00090 Aldo-keto reductase family 1 member C3 2
21865046 10.1016/j.bmc.2011.07.060 Unchecked 2
34454129 10.1016/j.bmc.2021.116372 Unchecked 2
22506594 10.1021/np201002x Aldo-keto reductase family 1 member C2 1
22506594 10.1021/np201002x Aldo-keto reductase family 1 member C1 1
34454129 10.1016/j.bmc.2021.116372 PNT2 1
21865046 10.1016/j.bmc.2011.07.060 NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine