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Compound Detail

CHEMBL472250

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CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)Cc3ccc(-c4cn(CCCCCCC(=O)NO)nn4)cc3)[C@H]2O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL472250
Phase Preclinical
Structure Type MOL
InChI Key OBRCETUNWRJYOJ-RNYCIUTISA-N
6
Targets
8
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

876.1
MW (Da)
3.80
ALogP
16
HBA
6
HBD
235.3
PSA (Ų)
0.06
QED
3
Ro5 Violations
15
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C45H73N5O12
MW 876.10
Aromatic Rings 2
Heavy Atoms 62
NP-Likeness 0.79

Activity Summary

IC50 5 meas. best 8.72
EC50 3 meas. best 5.98

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase (HDAC1 and HDAC2)
CHEMBL2111429
 IC50 8.72 8.72 1.9 2
Histone deacetylase 6
CHEMBL1865
 IC50 6.83 6.83 148.5 1
DU-145
CHEMBL613508
 EC50 5.98 5.98 1050.0 1
SK-MES-1
CHEMBL614923
 EC50 5.89 5.89 1280.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.86 5.86 1390.0 2
NCI-H69
CHEMBL614805
 EC50 5.83 5.83 1490.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase (HDAC1 and HDAC2) IC50 = 1.9 nM 8.72 Inhibition of HDAC1/2 from human HeLa cells nuclear extract by cell free fluorim... 19093884
Histone deacetylase (HDAC1 and HDAC2) IC50 = 1.9 nM 8.72 Inhibition of HDAC1/2 (unknown origin) 31499358
Histone deacetylase 6 IC50 = 148.5 nM 6.83 Inhibition of HDAC6 from human HeLa cells nuclear extract by cell free fluorimet... 19093884
DU-145 EC50 = 1050.0 nM 5.98 Cytotoxicity against human DU145 cells after 72 hrs by trypan blue exclusion ass... 19093884
SK-MES-1 EC50 = 1280.0 nM 5.89 Cytotoxicity against human SKMES1 cells after 72 hrs by trypan blue exclusion as... 19093884
Histone deacetylase 8 IC50 = 1390.0 nM 5.86 Inhibition of HDAC8 from human HeLa cells nuclear extract by cell free fluorimet... 19093884
Histone deacetylase 8 IC50 = 1390.0 nM 5.86 Inhibition of HDAC8 (unknown origin) 31499358
NCI-H69 EC50 = 1490.0 nM 5.83 Cytotoxicity against human NCI-H69 cells after 72 hrs by trypan blue exclusion a... 19093884

Literature References

PubMed DOI Target Context # Activities
19093884 10.1021/jm801128g Unchecked 2
19093884 10.1021/jm801128g Histone deacetylase (HDAC1 and HDAC2) 1
19093884 10.1021/jm801128g Histone deacetylase 8 1
19093884 10.1021/jm801128g Histone deacetylase 6 1
19093884 10.1021/jm801128g SK-MES-1 1
19093884 10.1021/jm801128g DU-145 1
19093884 10.1021/jm801128g ADMET 1
19093884 10.1021/jm801128g HMEC 1
19093884 10.1021/jm801128g Histone deacetylase 1
19093884 10.1021/jm801128g NCI-H69 1
31499358 10.1016/j.ejmech.2019.111662 Histone deacetylase (HDAC1 and HDAC2) 1
31499358 10.1016/j.ejmech.2019.111662 Histone deacetylase 8 1
31499358 10.1016/j.ejmech.2019.111662 Unchecked 1

Data from ChEMBL 36 via Core Engine