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Compound Detail

CHEMBL410525

O-ACETYLURSOLIC ACID
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CC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C(=O)O)CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C

Basic Information

ChEMBL ID CHEMBL410525
Name O-ACETYLURSOLIC ACID
Phase Preclinical
Structure Type MOL
InChI Key PHFUCJXOLZAQNH-OTMOLZNZSA-N
12
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

498.8
MW (Da)
7.66
ALogP
3
HBA
1
HBD
63.6
PSA (Ų)
0.31
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C32H50O4
MW 498.75
Aromatic Rings 0
Heavy Atoms 36
NP-Likeness 3.14

Activity Summary

IC50 13 meas. best 5.1
EC50 3 meas. best 5.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Streptococcus sp. 'group A'
CHEMBL612389
EC50 5.68 5.68 2111.0 1
Streptokinase A
CHEMBL1293228
EC50 5.55 5.55 2828.0 1
Streptococcus
CHEMBL612313
EC50 5.49 5.49 3261.0 1
Toxoplasma gondii
CHEMBL612888
IC50 5.1 5.1 7900.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.04 4.8533 9080.0 3
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.85 4.85 14270.0 1
Trypanosoma brucei
CHEMBL612849
IC50 4.77 4.77 17000.0 1
BGC-823
CHEMBL614526
IC50 4.71 4.71 19360.0 1
HT-29
CHEMBL384
IC50 4.62 4.62 23890.0 1
HepG2
CHEMBL395
IC50 4.42 4.42 37670.0 1
ASPC1
CHEMBL612588
IC50 4.15 4.15 71000.0 1
ADMET
CHEMBL612558
IC50 4.03 4.03 92940.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Streptococcus sp. 'group A' EC50 = 2111.0 nM 5.68 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptokinase A EC50 = 2828.0 nM 5.55 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus EC50 = 3261.0 nM 5.49 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Toxoplasma gondii IC50 = 7900.0 nM 5.1 Antiparasitic activity against Toxoplasma gondii 31585276
Plasmodium falciparum IC50 = 9080.0 nM 5.04 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 i... 29326018
Plasmodium falciparum IC50 = 12090.0 nM 4.92 Antiplasmodial activity against Plasmodium falciparum Dd2 incubated under low ox... 27112454
NON-PROTEIN TARGET IC50 = 14270.0 nM 4.85 Cytotoxicity against human NTUB1 cells after 72 hrs by MTT assay 19758808
Trypanosoma brucei IC50 = 17000.0 nM 4.77 Antitrypanosomal activity against Trypanosoma brucei S427 by microdilution metho... 15497942
BGC-823 IC50 = 19360.0 nM 4.71 Cytotoxicity against human BGC823 cells by MTT assay 21664827
HT-29 IC50 = 23890.0 nM 4.62 Cytotoxicity against human HT-29 cells incubated for 48 hrs by MTT assay 21664827
Plasmodium falciparum IC50 = 24930.0 nM 4.6 Antimalarial activity against chloroquine-resistant Plasmodium falciparum FcB1 a... 17967541
HepG2 IC50 = 37670.0 nM 4.42 Cytotoxicity against human HepG2 cells incubated for 48 hrs by MTT assay 21664827
ASPC1 IC50 = 71000.0 nM 4.15 Cytotoxicity against human AsPC1 cells after 72 hrs by MTT assay 22959527
ADMET IC50 = 92940.0 nM 4.03 Cytotoxicity against human GES-1 cells incubated for 48 hrs by MTT assay 21664827

Literature References

PubMed DOI Target Context # Activities
32345458 10.1016/j.bmc.2020.115527 Tyrosyl-DNA phosphodiesterase 1 2
19091579 10.1016/j.bmc.2008.11.036 HeLa 2
19091579 10.1016/j.bmc.2008.11.036 SK-OV-3 2
19091579 10.1016/j.bmc.2008.11.036 BGC-823 2
21439694 10.1016/j.ejmech.2011.02.053 Glycogen phosphorylase, muscle form 2
22959527 10.1016/j.bmc.2012.08.010 ASPC1 1
32092586 10.1016/j.ejmech.2020.112107 Ubiquitin carboxyl-terminal hydrolase 7 1
24844139 10.1021/jm5002293 ADMET 1
24844139 10.1021/jm5002293 Tryptophan 5-hydroxylase 1 1
- 10.1007/s00044-012-0397-z Cathepsin D 1
- 10.1007/s00044-012-0397-z MDA-MB-231 1
21664827 10.1016/j.bmc.2011.05.017 ADMET 1
21664827 10.1016/j.bmc.2011.05.017 BGC-823 1
21664827 10.1016/j.bmc.2011.05.017 HepG2 1
21664827 10.1016/j.bmc.2011.05.017 HT-29 1
17967541 10.1016/j.bmc.2007.10.031 Plasmodium falciparum 1
19758808 10.1016/j.bmc.2009.08.046 NON-PROTEIN TARGET 1
15497942 10.1021/np040059+ Trypanosoma brucei 1
15497942 10.1021/np040059+ Trypanosoma cruzi 1
18192087 10.1016/j.ejmech.2007.11.021 Aromatase 1

Data from ChEMBL 36 via Core Engine