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Compound Detail

CHEMBL4573938

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COc1ccc(-c2c(Nc3ccccn3)[nH]c3c(C4=CCCCC4)c(-c4ccccc4)nn3c2=O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4573938
Phase Preclinical
Structure Type MOL
InChI Key HSVRUECLQUGTDS-UHFFFAOYSA-N
5
Targets
10
Activities
1
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

489.6
MW (Da)
6.46
ALogP
6
HBA
2
HBD
84.3
PSA (Ų)
0.29
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C30H27N5O2
MW 489.58
Aromatic Rings 5
Heavy Atoms 37
NP-Likeness -0.76

Activity Summary

IC50 10 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
S-adenosylmethionine synthase isoform type-2
CHEMBL3313835
 IC50 9.4 7.992 0.4 5
HCT-116
CHEMBL394
 IC50 6.61 6.6 244.0 2
UDP-glucuronosyltransferase 1A1
CHEMBL1287617
 IC50 5.96 5.96 1100.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
 IC50 5.68 5.68 2100.0 1
Unchecked
CHEMBL612545
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 31.0 % Macaca mulatta
F 48.0 % Canis lupus familiaris
F 92.0 % Rattus norvegicus
Fu 0.015 - Homo sapiens
Fu 0.011 - Macaca mulatta
Fu 0.028 - Canis lupus familiaris
Fu 0.016 - Rattus norvegicus
Fu 0.0028 - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
S-adenosylmethionine synthase isoform type-2 IC50 = 0.3981 nM 9.4 Inhibition of MAT2a (unknown origin) using methionine and ATP as substrate asses... 38466661
S-adenosylmethionine synthase isoform type-2 IC50 = 10.0 nM 8.0 Inhibition of MAT2a in human HCT116- MTAP null cells assessed as reduction in sy... 38466661
S-adenosylmethionine synthase isoform type-2 IC50 = 14.0 nM 7.85 Inhibition of recombinant human MAT2A expressed in baculovirus infected Sf9 cell... 33829783
S-adenosylmethionine synthase isoform type-2 IC50 = 43.0 nM 7.37 Inhibition of human MAT2A 37591318
S-adenosylmethionine synthase isoform type-2 IC50 = 46.0 nM 7.34 Inhibition of recombinant MAT2A (unknown origin) expressed in baculovirus infect... 36961373
HCT-116 IC50 = 244.0 nM 6.61 Antiproliferative activity against human HCT-116 cells expressing MTAP-/- assess... 36961373
HCT-116 IC50 = 257.0 nM 6.59 Antiproliferative activity against MATP-null human HCT-116 cells isogenic cell m... 33829783
UDP-glucuronosyltransferase 1A1 IC50 = 1100.0 nM 5.96 Inhibition of UGT1A1 (unknown origin) 33829783
Solute carrier organic anion transporter family member 1B1 IC50 = 2100.0 nM 5.68 Inhibition of OATP1B1 (unknown origin) 33829783
Unchecked IC50 = 20000.0 nM 4.7 Inhibition of SAM production in human HCT-116 cells isogenic cell model measured... 33829783

Literature References

PubMed DOI Target Context # Activities
33829783 10.1021/acs.jmedchem.0c01895 ADMET 21
33829783 10.1021/acs.jmedchem.0c01895 KP-4 8
38466661 10.1021/acs.jmedchem.3c01860 S-adenosylmethionine synthase isoform type-2 4
33829783 10.1021/acs.jmedchem.0c01895 S-adenosylmethionine synthase isoform type-2 2
36961373 10.1021/acs.jmedchem.2c02006 HCT-116 2
37591318 10.1016/j.bmcl.2023.129450 S-adenosylmethionine synthase isoform type-1 2
37591318 10.1016/j.bmcl.2023.129450 S-adenosylmethionine synthase isoform type-2 2
33829783 10.1021/acs.jmedchem.0c01895 Cytochrome P450 2D6 2
33829783 10.1021/acs.jmedchem.0c01895 Cytochrome P450 2C19 2
33829783 10.1021/acs.jmedchem.0c01895 Cytochrome P450 2C9 2
33829783 10.1021/acs.jmedchem.0c01895 Cytochrome P450 3A4 2
33829783 10.1021/acs.jmedchem.0c01895 Nuclear receptor subfamily 1 group I member 2 2
33829783 10.1021/acs.jmedchem.0c01895 No relevant target 2
33829783 10.1021/acs.jmedchem.0c01895 HCT-116 2
33829783 10.1021/acs.jmedchem.0c01895 Solute carrier organic anion transporter family member 1B1 1
33829783 10.1021/acs.jmedchem.0c01895 Cytochrome P450 2B6 1
33829783 10.1021/acs.jmedchem.0c01895 UDP-glucuronosyltransferase 1A1 1
33829783 10.1021/acs.jmedchem.0c01895 Unchecked 1
36961373 10.1021/acs.jmedchem.2c02006 S-adenosylmethionine synthase isoform type-2 1
38116423 10.1021/acsmedchemlett.3c00488 HCT-116 1

Data from ChEMBL 36 via Core Engine