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Compound Detail

CHEMBL237111

AKBA
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CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2C(=O)C=C2[C@@H]4[C@@H](C)[C@H](C)CC[C@]4(C)CC[C@]23C)[C@@]1(C)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL237111
Name AKBA
Phase Preclinical
Structure Type MOL
InChI Key HMMGKOVEOFBCAU-BCDBGHSCSA-N

Known Names

3-acetyl-11-keto-beta-boswellic acid Akba
11
Targets
16
Activities
1
Assay Types
0
PK Parameters
20
Publications
2
Known Names

Molecular Properties

512.7
MW (Da)
6.84
ALogP
4
HBA
1
HBD
80.7
PSA (Ų)
0.41
QED
2
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C32H48O5
MW 512.73
Aromatic Rings 0
Heavy Atoms 37
NP-Likeness 3.12

Activity Summary

IC50 16 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 5.57 5.01 2700.0 2
Prostaglandin E synthase
CHEMBL5658
 IC50 5.52 5.52 3000.0 2
HUVEC
CHEMBL613979
 IC50 5.13 5.13 7450.0 1
Prolyl endopeptidase
CHEMBL3202
 IC50 5.1 5.1 7890.0 1
HL-60
CHEMBL383
 IC50 4.96 4.96 11000.0 1
A2780
CHEMBL614004
 IC50 4.85 4.85 14100.0 1
RAW264.7
CHEMBL612557
 IC50 4.81 4.81 15600.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.77 4.7367 16900.0 3
HT-29
CHEMBL384
 IC50 4.71 4.71 19400.0 1
HeLa
CHEMBL399
 IC50 4.51 4.51 31000.0 1
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1
CHEMBL2288
 IC50 4.3 4.29 50360.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 2700.0 nM 5.57 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
Prostaglandin E synthase IC50 = 3000.0 nM 5.52 Inhibition of mPGES1 in human A549 cell microsomal membrane using pGH2 as substr... 29329790
HUVEC IC50 = 7450.0 nM 5.13 Antiproliferation activity against HUVEC cells after 48 hrs by CCK-8 assay 25819335
Prolyl endopeptidase IC50 = 7890.0 nM 5.1 Inhibition of prolyl endopeptidase 15730241
HL-60 IC50 = 11000.0 nM 4.96 Cytotoxicity against human HL60 cells after 48 hrs by MTT assay 21334793
A2780 IC50 = 14100.0 nM 4.85 Cytotoxicity against human A2780 cells assessed as cell survival after 96 hrs by... 25618017
RAW264.7 IC50 = 15600.0 nM 4.81 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 23391590
NON-PROTEIN TARGET IC50 = 16900.0 nM 4.77 Cytotoxicity against human A253 cells assessed as cell survival after 96 hrs by ... 25618017
NON-PROTEIN TARGET IC50 = 17500.0 nM 4.76 Cytotoxicity against human HCT8 cells assessed as cell survival after 96 hrs by ... 25618017
HT-29 IC50 = 19400.0 nM 4.71 Cytotoxicity against human HT-29 cells assessed as cell survival after 96 hrs by... 25618017
NON-PROTEIN TARGET IC50 = 20900.0 nM 4.68 Cytotoxicity against human DLD1 cells assessed as cell survival after 96 hrs by ... 25618017
HeLa IC50 = 31000.0 nM 4.51 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 21334793
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 35600.0 nM 4.45 Inhibition of human recombinant 5-LOX expressed in insect cells assessed as decr... 31774676
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 IC50 = 50360.0 nM 4.3 Inhibition of recombinant N-terminal His6-tagged human Pin1 using Suc-Ala-Glu-ci... 30153964
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 IC50 = 52990.0 nM 4.28 Inhibition of Pin1 (unknown origin) using Suc-Ala-Glu-cis-Pro-Phe-4-nitroanilide... 27997878

Literature References

PubMed DOI Target Context # Activities
23013292 10.1021/np300009w Caco-2 23
23013292 10.1021/np300009w No relevant target 17
23013292 10.1021/np300009w Plasma 3
25618017 10.1016/j.ejmech.2015.01.039 NON-PROTEIN TARGET 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
23013292 10.1021/np300009w Brain 2
23013292 10.1021/np300009w ADMET 2
23391590 10.1016/j.bmcl.2012.12.086 RAW264.7 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
26711891 10.1016/j.bmcl.2015.11.035 PBMC 2
26711891 10.1016/j.bmcl.2015.11.035 Mus musculus 2
31774676 10.1021/acs.jnatprod.9b00538 Polyunsaturated fatty acid lipoxygenase ALOX15B 2
31774676 10.1021/acs.jnatprod.9b00538 Prostaglandin G/H synthase 2 2
30153964 10.1016/j.bmcl.2018.08.021 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 2
31774676 10.1021/acs.jnatprod.9b00538 Polyunsaturated fatty acid 5-lipoxygenase 2
31774676 10.1021/acs.jnatprod.9b00538 Prostaglandin G/H synthase 1 2
22123322 10.1016/j.bmcl.2011.10.112 HT-29 1
22123322 10.1016/j.bmcl.2011.10.112 SW-620 1
10978197 10.1021/np000069k Polyunsaturated fatty acid 5-lipoxygenase 1
17950603 10.1016/j.bmcl.2007.10.011 HT-29 1

Data from ChEMBL 36 via Core Engine