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Compound Detail

CHEMBL289159

TRYPROSTATIN A
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COc1ccc2c(C[C@@H]3NC(=O)[C@@H]4CCCN4C3=O)c(CC=C(C)C)[nH]c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL289159
Name TRYPROSTATIN A
Phase Preclinical
Structure Type MOL
InChI Key XNRPVPHNDQHWLJ-PMACEKPBSA-N
4
Targets
6
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

381.5
MW (Da)
2.72
ALogP
3
HBA
2
HBD
74.4
PSA (Ų)
0.78
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H27N3O3
MW 381.48
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 1.20

Activity Summary

IC50 4 meas. best 5.47
Kd 1 meas. best 7.99
Ki 1 meas. best 6.84

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Oxysterols receptor LXR-alpha
CHEMBL2808
 Kd 7.99 7.99 10.2 1
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
 Ki 6.84 6.84 145.0 1
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
 IC50 5.47 5.47 3387.0 1
K562
CHEMBL385
 IC50 4.39 4.39 41000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.17 4.17 68000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Oxysterols receptor LXR-alpha Kd = 10.2 nM 7.99 Binding affinity to full length human LXRalpha assessed as dissociation constant... 38334086
CDGSH iron-sulfur domain-containing protein 1 Ki = 145.0 nM 6.84 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
CDGSH iron-sulfur domain-containing protein 1 IC50 = 3387.0 nM 5.47 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
K562 IC50 = 41000.0 nM 4.39 Cytotoxicity against human K562 cells after 48 hrs by MTT assay 19256529
NON-PROTEIN TARGET IC50 = 68000.0 nM 4.17 Antiproliferative activity against mouse tsFT210 cells after 48 hrs by WST-8 ass... 18321710

Literature References

PubMed DOI Target Context # Activities
38334086 10.1021/acs.jnatprod.3c01029 Mus musculus 32
18321710 10.1016/j.bmc.2008.02.050 NON-PROTEIN TARGET 5
38334086 10.1021/acs.jnatprod.3c01029 Oxysterols receptor LXR-alpha 5
38334086 10.1021/acs.jnatprod.3c01029 HepG2 4
18321710 10.1016/j.bmc.2008.02.050 MCF7 3
18321710 10.1016/j.bmc.2008.02.050 PC-3 3
11931609 10.1021/jm0155953 MCF7 2
27687671 10.1016/j.bmcl.2016.09.009 CDGSH iron-sulfur domain-containing protein 1 2
27865702 10.1016/j.bmcl.2016.11.013 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
30953881 10.1016/j.ejmech.2019.03.025 Unchecked 2
38334086 10.1021/acs.jnatprod.3c01029 Unchecked 2
11931609 10.1021/jm0155953 PC-3 2
11931609 10.1021/jm0155953 NCI-H520 2
18321710 10.1016/j.bmc.2008.02.050 SR 1
18321710 10.1016/j.bmc.2008.02.050 HOP-92 1
18321710 10.1016/j.bmc.2008.02.050 EKVX 1
18321710 10.1016/j.bmc.2008.02.050 COLO 205 1
18321710 10.1016/j.bmc.2008.02.050 MOLT-4 1
18321710 10.1016/j.bmc.2008.02.050 K562 1
18321710 10.1016/j.bmc.2008.02.050 IGROV-1 1

Data from ChEMBL 36 via Core Engine