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Compound Detail

CHEMBL1478

LITHOCHOLIC ACID
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C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Basic Information

ChEMBL ID CHEMBL1478
Name LITHOCHOLIC ACID
Phase Preclinical
Structure Type MOL
InChI Key SMEROWZSTRWXGI-HVATVPOCSA-N
20
Targets
44
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

376.6
MW (Da)
5.51
ALogP
2
HBA
2
HBD
57.5
PSA (Ų)
0.68
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C24H40O3
MW 376.58
Aromatic Rings 0
Heavy Atoms 27
NP-Likeness 2.32

Activity Summary

IC50 27 meas. best 7.74
EC50 12 meas. best 6.37
Kd 4 meas. best 6.48
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bile acid receptor
CHEMBL2047
IC50 7.74 7.74 18.3 1
Vitamin D3 receptor
CHEMBL1977
Kd 6.48 5.4067 330.0 3
G-protein coupled bile acid receptor 1
CHEMBL5409
EC50 6.37 5.9643 431.0 7
Vitamin D3 receptor
CHEMBL1977
EC50 5.67 5.67 2140.0 1
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
IC50 5.57 5.16 2710.0 3
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1
CHEMBL1795098
IC50 5.32 5.32 4823.0 1
Tyrosine-protein phosphatase non-receptor type 2
CHEMBL3807
IC50 5.21 4.95 6120.0 2
Bile acid receptor
CHEMBL2047
EC50 5.17 4.935 6700.0 2
HSP60/HSP10
CHEMBL4106131
IC50 5.0 5.0 10000.0 1
Vitamin D3 receptor
CHEMBL1977
IC50 4.87 4.6 13600.0 2
Tumour suppressor protein p53/Mdm4
CHEMBL2221344
Kd 4.82 4.82 15000.0 1
GroEL/GroES
CHEMBL4106139
IC50 4.8 4.515 16000.0 2
Unchecked
CHEMBL612545
IC50 4.74 4.74 18100.0 1
CMP-N-acetylneuraminate-beta-1,4-galactoside alpha-2,3-sialyltransferase
CHEMBL3211
IC50 4.68 4.68 21000.0 1
CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1
CHEMBL3596074
IC50 4.68 4.68 21000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.64 4.325 23000.0 2
Plasmodium falciparum
CHEMBL364
IC50 4.57 4.57 26900.0 1
HepG2
CHEMBL395
EC50 4.3 4.3 50000.0 2
Ephrin type-A receptor 2
CHEMBL2068
IC50 4.3 4.27 50000.0 2
Caco-2
CHEMBL614058
IC50 4.25 4.25 56000.0 1
Ephrin type-A receptor 2
CHEMBL4105859
IC50 4.24 4.17 57000.0 2
N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
CHEMBL4630839
IC50 4.17 4.17 68000.0 1
HCT-116
CHEMBL394
IC50 4.09 4.09 81100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bile acid receptor IC50 = 18.3 nM 7.74 Antagonist activity at human GST-tagged FXR after 20 mins by TR-FRET assay 24775917
Vitamin D3 receptor Kd = 330.0 nM 6.48 Binding affinity to N-terminal His-tagged human VDR LBD canonical site (118 to 4... 24818857
G-protein coupled bile acid receptor 1 EC50 = 431.0 nM 6.37 Agonist activity at human TGR5 expressed in HEK293-A cells co-transfected with E... 38996653
G-protein coupled bile acid receptor 1 EC50 = 530.0 nM 6.28 Agonist activity at human TGR5 38691888
G-protein coupled bile acid receptor 1 EC50 = 580.0 nM 6.24 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
G-protein coupled bile acid receptor 1 EC50 = 680.0 nM 6.17 Agonist activity at human GPBAR1 expressed in HEK293 cells assessed as increase ... 25735208
G-protein coupled bile acid receptor 1 EC50 = 730.0 nM 6.14 Agonist activity at wild type TGR5 (unknown origin) 24900622
Vitamin D3 receptor EC50 = 2140.0 nM 5.67 Agonist activity at VP16 tagged-VDR-LBD (unknown origin) expressed in HEK293T ce... 26774929
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 2710.0 nM 5.57 Inhibition of PTP1B (unknown origin) by SpectraMax 340 microplate reader Analysi... 34000484
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 IC50 = 4823.0 nM 5.32 PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS hits for Scp-1 phosphatase ... -
G-protein coupled bile acid receptor 1 EC50 = 5000.0 nM 5.3 Agonist activity at TGR5 expressed in NCI-H716 cells assessed as cAMP level afte... 24900463
G-protein coupled bile acid receptor 1 EC50 = 5600.0 nM 5.25 Agonist activity at TGR5 expressed in CHO cells by CRE-driven luciferase reporte... 19911773
Tyrosine-protein phosphatase non-receptor type 2 IC50 = 6120.0 nM 5.21 Inhibition of TCPTP (unknown origin) by SpectraMax 340 microplate reader Analysi... 34000484
Bile acid receptor EC50 = 6700.0 nM 5.17 Agonist activity at human FXR expressed in COS1 cells by luciferase reporter gen... 19911773
Vitamin D3 receptor Kd = 9520.0 nM 5.02 Binding affinity to N-terminal His-tagged human VDR LBD low-affinity site (118 t... 24818857
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 9620.0 nM 5.02 Inhibition of PTP1B (unknown origin) using DiFMUP as substrate incubated for 10 ... 38723203
HSP60/HSP10 IC50 = 10000.0 nM 5.0 Inhibition of human N-terminal octa-His-tagged HSP60 expressed in Escherichia co... 30852084
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 12740.0 nM 4.89 Inhibition of PTP1B by para-nitrophenyl phosphate release assay 23067554
Vitamin D3 receptor IC50 = 13600.0 nM 4.87 Antagonist activity against VDR-LBD (unknown origin) expressed in Escherichia co... 26774929
Tumour suppressor protein p53/Mdm4 Kd = 15000.0 nM 4.82 Inhibition of MDMX/p53 (unknown origin) interaction -

Literature References

PubMed DOI Target Context # Activities
30108740 10.1039/C7MD00475C HUVEC 11
- 10.6019/CHEMBL5058564 HEK-293T 9
25685308 10.1039/c4md00223g HCT-116 9
- 10.6019/CHEMBL5058564 U2OS 9
24818857 10.1021/jm5002524 Vitamin D3 receptor 8
- 10.6019/CHEMBL5058564 Fibroblast 8
24900622 10.1021/ml400247k Unchecked 6
26774929 10.1016/j.ejmech.2016.01.002 Vitamin D3 receptor 6
17963371 10.1021/jm0707931 Bile acid receptor 5
30852084 10.1016/j.bmcl.2019.02.028 Unchecked 5
24900622 10.1021/ml400247k G-protein coupled bile acid receptor 1 5
- 10.6019/CHEMBL5303304 U2OS 5
- 10.6019/CHEMBL5303304 Fibroblast 4
- 10.6019/CHEMBL5303304 HEK-293T 4
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
18768321 10.1016/j.bmc.2008.07.046 NON-PROTEIN TARGET 4
18768321 10.1016/j.bmc.2008.07.046 HCT-116 4
18768321 10.1016/j.bmc.2008.07.046 GBM 4
25685308 10.1039/c4md00223g NON-PROTEIN TARGET 4
39149112 10.1039/d4md00007b Plasmodium falciparum 4

Data from ChEMBL 36 via Core Engine