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Compound Detail

CHEMBL437964

11-KETO BOSWELLIC ACID
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C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC(=O)[C@@H]4[C@@]5(C)CC[C@@H](O)[C@](C)(C(=O)O)[C@@H]5CC[C@]43C)[C@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL437964
Name 11-KETO BOSWELLIC ACID
Phase Preclinical
Structure Type MOL
InChI Key YIMHGPSYDOGBPI-YZCVQEKWSA-N
10
Targets
16
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

470.7
MW (Da)
6.27
ALogP
3
HBA
2
HBD
74.6
PSA (Ų)
0.47
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C30H46O4
MW 470.69
Aromatic Rings 0
Heavy Atoms 34
NP-Likeness 3.14

Activity Summary

IC50 16 meas. best 5.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 5.52 5.035 3000.0 2
Prostaglandin E synthase
CHEMBL5658
 IC50 5.52 5.26 3000.0 2
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 5.09 5.09 8040.0 3
Tyrosine-protein phosphatase non-receptor type 2
CHEMBL3807
 IC50 5.03 5.03 9450.0 1
HL-60
CHEMBL383
 IC50 4.5 4.5 32000.0 1
Prolyl endopeptidase
CHEMBL3202
 IC50 4.44 4.44 36320.0 1
A2780
CHEMBL614004
 IC50 4.42 4.42 37900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.35 4.31 44600.0 3
HeLa
CHEMBL399
 IC50 4.3 4.3 50000.0 1
HT-29
CHEMBL384
 IC50 4.14 4.14 71900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 3000.0 nM 5.52 Inhibition of lipoxygenase 5 product formation from endogenous substrate in Calc... 10978197
Prostaglandin E synthase IC50 = 3000.0 nM 5.52 Inhibition of microsomal PGES1 isolated from IL-1beta-stimulated human A549 cell... 24844534
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 8040.0 nM 5.09 Inhibition of PTP1B by pNPP assay 18707891
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 8040.0 nM 5.09 Inhibition of PTP1B (unknown origin) -
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 8040.0 nM 5.09 Inhibition of PTP1B (unknown origin) -
Tyrosine-protein phosphatase non-receptor type 2 IC50 = 9450.0 nM 5.03 Inhibition of TCPTP by pNPP assay 18707891
Prostaglandin E synthase IC50 = 10000.0 nM 5.0 Inhibition of mPGES1 in human A549 cell microsomal membrane using pGH2 as substr... 29329790
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 28300.0 nM 4.55 Inhibition of human recombinant 5-LOX expressed in insect cells assessed as decr... 31774676
HL-60 IC50 = 32000.0 nM 4.5 Cytotoxicity against human HL60 cells after 48 hrs by MTT assay 21334793
Prolyl endopeptidase IC50 = 36320.0 nM 4.44 Inhibition of prolyl endopeptidase 15730241
A2780 IC50 = 37900.0 nM 4.42 Cytotoxicity against human A2780 cells assessed as cell survival after 96 hrs by... 25618017
NON-PROTEIN TARGET IC50 = 44600.0 nM 4.35 Cytotoxicity against human HCT8 cells assessed as cell survival after 96 hrs by ... 25618017
NON-PROTEIN TARGET IC50 = 45900.0 nM 4.34 Cytotoxicity against human A253 cells assessed as cell survival after 96 hrs by ... 25618017
HeLa IC50 = 50000.0 nM 4.3 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 21334793
NON-PROTEIN TARGET IC50 = 57700.0 nM 4.24 Cytotoxicity against human DLD1 cells assessed as cell survival after 96 hrs by ... 25618017
HT-29 IC50 = 71900.0 nM 4.14 Cytotoxicity against human HT-29 cells assessed as cell survival after 96 hrs by... 25618017

Literature References

PubMed DOI Target Context # Activities
23013292 10.1021/np300009w Caco-2 23
23013292 10.1021/np300009w No relevant target 19
26010018 10.1016/j.ejmech.2015.05.001 Rattus norvegicus 3
25618017 10.1016/j.ejmech.2015.01.039 NON-PROTEIN TARGET 3
31774676 10.1021/acs.jnatprod.9b00538 Prostaglandin G/H synthase 2 2
26711891 10.1016/j.bmcl.2015.11.035 PBMC 2
17481895 10.1016/j.bmcl.2007.04.034 Rattus norvegicus 2
23013292 10.1021/np300009w Plasma 2
31774676 10.1021/acs.jnatprod.9b00538 Prostaglandin G/H synthase 1 2
- 10.1007/s00044-010-9529-5 Tyrosine-protein phosphatase non-receptor type 1 2
31774676 10.1021/acs.jnatprod.9b00538 Polyunsaturated fatty acid lipoxygenase ALOX15B 2
23013292 10.1021/np300009w Brain 2
26711891 10.1016/j.bmcl.2015.11.035 Mus musculus 2
31774676 10.1021/acs.jnatprod.9b00538 Polyunsaturated fatty acid 5-lipoxygenase 2
20100662 10.1016/j.bmc.2010.01.010 11-beta-hydroxysteroid dehydrogenase 1 1
21334793 10.1016/j.ejmech.2011.01.061 HeLa 1
21334793 10.1016/j.ejmech.2011.01.061 HL-60 1
20100662 10.1016/j.bmc.2010.01.010 11-beta-hydroxysteroid dehydrogenase type 2 1
35500202 10.1021/acs.jnatprod.1c01166 Sentrin-specific protease 1 1
17950603 10.1016/j.bmcl.2007.10.011 HT-29 1

Data from ChEMBL 36 via Core Engine