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Compound Detail

CHEMBL34241

ROTTLERIN
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CC(=O)c1c(O)c(C)c(O)c(Cc2c(O)c3c(c(C(=O)/C=C/c4ccccc4)c2O)OC(C)(C)C=C3)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL34241
Name ROTTLERIN
Phase Preclinical
Structure Type MOL
InChI Key DEZFNHCVIZBHBI-ZHACJKMWSA-N
17
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

516.5
MW (Da)
5.40
ALogP
8
HBA
5
HBD
144.5
PSA (Ų)
0.22
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C30H28O8
MW 516.55
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness 1.72

Activity Summary

IC50 28 meas. best 6.6
EC50 1 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hep 3B2
CHEMBL4296437
 IC50 6.6 6.6 250.0 1
Huh-7
CHEMBL614039
 IC50 6.24 6.24 570.0 1
Malate dehydrogenase
CHEMBL4255
 IC50 6.16 6.16 700.0 1
Lyssavirus rabies
CHEMBL4513192
 EC50 6.0 6.0 1000.0 1
Beta-lactamase
CHEMBL2026
 IC50 5.92 5.1175 1200.0 4
Unchecked
CHEMBL612545
 IC50 5.92 5.92 1200.0 1
MAP kinase-activated protein kinase 5
CHEMBL3094
 IC50 5.72 5.72 1900.0 2
Protein kinase C delta type
CHEMBL2996
 IC50 5.52 5.52 3000.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.5 5.3143 3162.3 7
Eukaryotic elongation factor 2 kinase
CHEMBL5026
 IC50 5.28 5.28 5300.0 1
MAP kinase-activated protein kinase 2
CHEMBL2208
 IC50 5.27 5.27 5400.0 1
MIA PaCa-2
CHEMBL614725
 IC50 5.1 5.1 8000.0 1
Ubiquitin carboxyl-terminal hydrolase 1/WD repeat-containing protein 48
CHEMBL3430885
 IC50 5.1 5.1 8000.0 1
HL-60
CHEMBL383
 IC50 5.05 5.05 9000.0 1
RuvB-like 1
CHEMBL3259467
 IC50 5.0 5.0 10000.0 1
Chymotrypsinogen B
CHEMBL4796
 IC50 4.6 4.6 25000.0 1
Beta-lactamase
CHEMBL2725
 IC50 4.02 4.02 96000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hep 3B2 IC50 = 250.0 nM 6.6 Anticancer activity against human Hep3B cells assessed as inhibition of cell pro... 33873056
Huh-7 IC50 = 570.0 nM 6.24 Anticancer activity against human Huh-7 cells assessed as inhibition of cell pro... 33873056
Malate dehydrogenase IC50 = 700.0 nM 6.16 Inhibitory activity against malate dehydrogenase (MDH) from Thermus flavus 12672248
Lyssavirus rabies EC50 = 1000.0 nM 6.0 Antiviral activity against RABV 33539089
Beta-lactamase IC50 = 1200.0 nM 5.92 Inhibitory activity against Amp C beta-Lactamase 13678405
Unchecked IC50 = 1200.0 nM 5.92 Inhibition of beta-lactamase from Escherichia coli 12672248
Beta-lactamase IC50 = 1800.0 nM 5.75 Inhibition of 1 nM AmpC beta lactamase 17149857
MAP kinase-activated protein kinase 5 IC50 = 1900.0 nM 5.72 Inhibition of p38-regulated activated kinase (PRAK) 12672248
MAP kinase-activated protein kinase 5 IC50 = 1900.0 nM 5.72 Inhibition of His-tagged human PRAK expressed in Sf9 cells 10998351
Protein kinase C delta type IC50 = 3000.0 nM 5.52 Inhibition of Protein kinase C delta (PKCdelta) 12672248
Protein kinase C delta type IC50 = 3000.0 nM 5.52 Inhibition of PKCdelta (unknown origin) by IMAP kinase assay 35167283
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 3981.07 nM 5.4 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Eukaryotic elongation factor 2 kinase IC50 = 5300.0 nM 5.28 Inhibition of eEF2K (unknown origin) 32717479
MAP kinase-activated protein kinase 2 IC50 = 5400.0 nM 5.27 Inhibition of His-tagged human MAPKAPK2 expressed in Escherichia coli at 10 uM 10998351
MIA PaCa-2 IC50 = 8000.0 nM 5.1 Cytotoxicity against human MIAPaCa2 cells after 48 hrs by MTT assay 24041234
Ubiquitin carboxyl-terminal hydrolase 1/WD repeat-containing protein 48 IC50 = 8000.0 nM 5.1 Inhibition of human USP1/UAF1 complex using Ub-Rho as substrate by qHTS assay 27362876

Literature References

PubMed DOI Target Context # Activities
19281222 10.1021/jm801605r AmpC 40
24041234 10.1021/np400433g HL-60 28
31017784 10.1021/acs.jnatprod.8b00917 No relevant target 15
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
10998351 10.1042/0264-6021:3510095 Unchecked 5
31223449 10.1021/acsmedchemlett.9b00093 Beta-lactamase 4
17149857 10.1021/jm061103g Beta-lactamase 4
13678405 10.1021/jm030266r Beta-lactamase 3
18223646 10.1038/nchembio.65 Eukaryotic peptide chain release factor GTP-binding subunit 3
18223646 10.1038/nchembio.65 Unchecked 3
18157122 10.1038/nchembio.2007.59 Janus Kinase (JAK) 2
17850214 10.1042/bj20070797 Unchecked 2
31223449 10.1021/acsmedchemlett.9b00093 Chymotrypsinogen A 2
18328716 10.1016/j.bmc.2008.02.054 Tyrosine-protein kinase SYK 2
12672248 10.1021/jm020427b Beta-lactamase 2
10998351 10.1042/0264-6021:3510095 MAP kinase-activated protein kinase 2 2
10998351 10.1042/0264-6021:3510095 MAP kinase-activated protein kinase 5 2
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 2
17850214 10.1042/bj20070797 Ribosomal protein S6 kinase alpha-1 1
17850214 10.1042/bj20070797 Rho-associated protein kinase 2 1

Data from ChEMBL 36 via Core Engine