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Compound Detail

CHEMBL117021

LYSOPHOSPHATIDIC ACID
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CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL117021
Name LYSOPHOSPHATIDIC ACID
Phase Preclinical
Structure Type MOL
InChI Key WRGQSWVCFNIUNZ-GDCKJWNLSA-N
10
Targets
31
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

436.5
MW (Da)
5.04
ALogP
5
HBA
3
HBD
113.3
PSA (Ų)
0.11
QED
1
Ro5 Violations
20
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H41O7P
MW 436.53
Aromatic Rings 0
Heavy Atoms 29
NP-Likeness 1.08

Activity Summary

EC50 25 meas. best 8.7
IC50 3 meas. best 8.0
Kd 2 meas. best 8.25
Ki 1 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysophosphatidic acid receptor 2
CHEMBL3724
 EC50 8.7 7.9875 2.0 4
Unchecked
CHEMBL612545
 EC50 8.3 8.3 5.0 1
Lysophosphatidic acid receptor 1
CHEMBL3819
 Kd 8.25 8.25 5.6 1
Lysophosphatidic acid receptor 4
CHEMBL5968
 EC50 8.09 8.09 8.1 2
Unchecked
CHEMBL612545
 IC50 8.0 8.0 10.0 1
Lysophosphatidic acid receptor 5
CHEMBL5700
 EC50 7.92 7.1825 12.0 4
Lysophosphatidic acid receptor 1
CHEMBL3819
 EC50 7.77 7.22 17.0 6
Lysophosphatidic acid receptor 3
CHEMBL3250
 EC50 7.11 6.76 77.0 5
Autotaxin
CHEMBL3691
 Ki 7.0 7.0 100.0 1
Lysophosphatidic acid receptor 4
CHEMBL3321650
 EC50 6.58 6.58 260.0 1
Autotaxin
CHEMBL3691
 IC50 6.36 6.33 442.0 2
Transient receptor potential cation channel subfamily V member 1
CHEMBL4794
 Kd 6.12 6.12 754.0 1
Lysophosphatidic acid receptor 6
CHEMBL2331058
 EC50 6.01 6.01 970.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysophosphatidic acid receptor 2 EC50 = 2.0 nM 8.7 Agonist activity at human LPA2 expressed in LPA1xLPA2 double knockout mouse MEF ... 25100502
Unchecked EC50 = 5.0 nM 8.3 Relative potency was evaluated for its ability to mobilize intracellular calcium... 10090779
Lysophosphatidic acid receptor 1 Kd = 5.6 nM 8.25 Binding affinity to LPA1 receptor (unknown origin) by cell-based backscattering ... 31790581
Lysophosphatidic acid receptor 2 EC50 = 6.8 nM 8.17 Agonistic activity against lysophosphatidic acid receptor 2 using [35S]GTP-gamma... 15177455
Lysophosphatidic acid receptor 4 EC50 = 8.1 nM 8.09 Agonist activity at human LPA4 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 4 EC50 = 8.128 nM 8.09 Agonist activity at human LPA4 receptor transfected in HEK293 cells after 1 hr b... 23395664
Unchecked IC50 = 10.0 nM 8.0 Displacement of [32P]diazirine-LPA from LPA receptor in mouse N1E-115 cells prei... -
Lysophosphatidic acid receptor 5 EC50 = 12.0 nM 7.92 Agonist activity at LPA5 expressed in human chem1 cells assessed as intracellula... 20056548
Lysophosphatidic acid receptor 1 EC50 = 17.0 nM 7.77 Agonistic activity against lysophosphatidic acid receptor 1 using [35S]GTP-gamma... 15177455
Lysophosphatidic acid receptor 1 EC50 = 18.0 nM 7.75 Agonist activity at human LPA1 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 1 EC50 = 17.78 nM 7.75 Agonist activity at human LPA1 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 2 EC50 = 29.0 nM 7.54 Agonist activity at human LPA2 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 2 EC50 = 28.84 nM 7.54 Agonist activity at human LPA2 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 1 EC50 = 31.0 nM 7.51 Agonist activity at LPA1 expressed in human chem1 cells assessed as intracellula... 20056548
Lysophosphatidic acid receptor 5 EC50 = 55.0 nM 7.26 Agonist activity at human LPA5 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 5 EC50 = 54.95 nM 7.26 Agonist activity at human LPA5 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 3 EC50 = 77.62 nM 7.11 Agonist activity at human LPA3 receptor transfected in HEK293 cells after 1 hr b... 23395664
Lysophosphatidic acid receptor 3 EC50 = 77.0 nM 7.11 Agonist activity at human LPA3 receptor transfected in HEK293 cells after 1 hr b... 23395664
Autotaxin Ki = 100.0 nM 7.0 Noncompetitive type inhibition of human autotaxin at free state isolated from MD... 20041668
Lysophosphatidic acid receptor 3 EC50 = 120.0 nM 6.92 Agonist activity at LPA3 expressed in human chem1 cells assessed as intracellula... 20056548

Literature References

PubMed DOI Target Context # Activities
31790581 10.1021/acs.jmedchem.9b01287 Lysophosphatidic acid receptor 1 11
20536182 10.1021/jm1005012 Autotaxin 4
23395664 10.1016/j.bmcl.2013.01.002 Lysophosphatidic acid receptor 1 3
23395664 10.1016/j.bmcl.2013.01.002 Lysophosphatidic acid receptor 2 3
23395664 10.1016/j.bmcl.2013.01.002 Lysophosphatidic acid receptor 3 3
23395664 10.1016/j.bmcl.2013.01.002 Lysophosphatidic acid receptor 5 3
23395664 10.1016/j.bmcl.2013.01.002 Lysophosphatidic acid receptor 6 3
23395664 10.1016/j.bmcl.2013.01.002 Lysophosphatidic acid receptor 4 3
22460025 10.1016/j.bmcl.2012.03.008 Autotaxin 2
15177455 10.1016/j.bmcl.2004.04.061 Lysophosphatidic acid receptor 1 2
15177455 10.1016/j.bmcl.2004.04.061 Lysophosphatidic acid receptor 3 2
15177455 10.1016/j.bmcl.2004.04.061 Lysophosphatidic acid receptor 2 2
16680159 10.1038/nchembio790 PC-3 1
22460025 10.1016/j.bmcl.2012.03.008 ADMET 1
20056548 10.1016/j.bmc.2009.12.020 Lysophosphatidic acid receptor 5 1
20056548 10.1016/j.bmc.2009.12.020 Lysophosphatidic acid receptor 3 1
20056548 10.1016/j.bmc.2009.12.020 Lysophosphatidic acid receptor 1 1
20041668 10.1021/jm9012328 Autotaxin 1
10090779 10.1021/jm970809v Unchecked 1
25100502 10.1021/jm5007116 Lysophosphatidic acid receptor 2 1

Data from ChEMBL 36 via Core Engine