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Compound Detail

CHEMBL114606

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CCCCCCCCc1ccc(CCC(N)(CO)COP(=O)(O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL114606
Phase Preclinical
Structure Type MOL
InChI Key LRFKWQGGENFBFO-UHFFFAOYSA-N
7
Targets
52
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

387.5
MW (Da)
3.32
ALogP
4
HBA
4
HBD
113.0
PSA (Ų)
0.29
QED
0
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H34NO5P
MW 387.46
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 0.90

Activity Summary

EC50 40 meas. best 10.7
IC50 12 meas. best 10.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 IC50 10.85 9.9833 0.0 3
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 EC50 10.7 9.162 0.0 15
Sphingosine 1-phosphate receptor 4
CHEMBL3230
 EC50 10.05 8.652 0.1 5
Sphingosine 1-phosphate receptor 3
CHEMBL3892
 EC50 10.0 8.206 0.1 10
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 EC50 9.4 8.4443 0.4 7
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 IC50 9.11 9.11 0.8 1
Sphingosine 1-phosphate receptor 2
CHEMBL2955
 IC50 9.11 7.535 0.8 2
Unchecked
CHEMBL612545
 IC50 8.92 8.92 1.2 1
Mus musculus
CHEMBL375
 EC50 8.25 8.25 5.6 1
Sphingosine 1-phosphate receptor 3
CHEMBL3892
 IC50 8.2 8.2 6.3 2
Sphingosine 1-phosphate receptor 4
CHEMBL3230
 IC50 7.82 7.82 15.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 4910.0 ng.hr.mL-1 Rattus norvegicus
CL 17.8 mL.min-1.kg-1 Rattus norvegicus
Cmax 992.62 nM Rattus norvegicus
T1/2 7.6 hr Rattus norvegicus
T1/2 25.2 hr Rattus norvegicus
Tmax 6.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingosine 1-phosphate receptor 1 IC50 = 0.014 nM 10.85 Displacement of 33-P-S1P from from human S1P receptor expressed in CHO cell memb... 26985316
Sphingosine 1-phosphate receptor 1 EC50 = 0.02 nM 10.7 Agonist activity at human recombinant S1P1 expressed in CHO cells assessed as st... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 0.07 nM 10.15 Agonist activity at human S1P1 receptor expressed in CHO cells co-expressing GFP... 26985316
Sphingosine 1-phosphate receptor 1 EC50 = 0.07 nM 10.15 Agonist activity at human recombinant C-terminal GFP-fused S1P1 expressed in CHO... 33492963
Sphingosine 1-phosphate receptor 4 EC50 = 0.09 nM 10.05 Agonist activity at human S1P4 receptor by GTPgammaS binding assay 26985316
Sphingosine 1-phosphate receptor 3 EC50 = 0.1 nM 10.0 Activity at human S1P3 receptor expressed in HEK293T cells by [35S]GTP-gamma-S b... 17113298
Sphingosine 1-phosphate receptor 1 IC50 = 0.28 nM 9.55 Inhibition of [33P]-S1P binding to human Sphingosine 1-phosphate receptor 1 expr... 15149705
Sphingosine 1-phosphate receptor 1 IC50 = 0.28 nM 9.55 Displacement of [33P]sphingosine 1 phosphate from human S1P1 receptor expressed ... 15615513
Sphingosine 1-phosphate receptor 1 EC50 = 0.3 nM 9.52 Activity at human S1P1 receptor expressed in CHO cells by [35S]GTPgammaS binding... 15615513
Sphingosine 1-phosphate receptor 1 EC50 = 0.35 nM 9.46 Agonist activity at human S1P1 receptor expressed in human Chem1 cells assessed ... 20337461
Sphingosine 1-phosphate receptor 1 EC50 = 0.377 nM 9.42 Agonist activity at human S1P1 receptor by GTPgammaS binding assay 26985316
Sphingosine 1-phosphate receptor 5 EC50 = 0.4 nM 9.4 Agonist activity at human S1P5 receptor by GTPgammaS binding assay 26985316
Sphingosine 1-phosphate receptor 5 EC50 = 0.67 nM 9.17 Agonist activity at recombinant human S1P5 expressed in CHO cell membranes asses... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 0.7 nM 9.15 Agonist activity at recombinant human S1P1 expressed in CHO cell membranes asses... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 0.7 nM 9.15 Agonist activity at S1P1 receptor (unknown origin) expressed in PathHunter HEK 2... 35077170
Sphingosine 1-phosphate receptor 2 IC50 = 0.77 nM 9.11 Inhibition of [33P]-S1P binding to human Sphingosine 1-phosphate receptor 5 expr... 15149705
Sphingosine 1-phosphate receptor 5 IC50 = 0.77 nM 9.11 Displacement of [33P]sphingosine 1 phosphate from human S1P5 receptor expressed ... 15615513
Unchecked IC50 = 1.2 nM 8.92 Antimigratory activity against human T cells assessed as inhibition of S1P-induc... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 1.2 nM 8.92 Agonism of human S1P-1 receptor expressed in CHO cells, 90-120 min in pH 7.4 usi... 16078855
Sphingosine 1-phosphate receptor 1 EC50 = 1.3 nM 8.89 Activity at human S1P1 receptor expressed in HEK293T cells by [35S]GTP-gamma-S b... 17113298

Literature References

PubMed DOI Target Context # Activities
30292898 10.1016/j.ejmech.2018.09.043 Histone deacetylase 14
33492963 10.1021/acs.jmedchem.0c01109 Sphingosine 1-phosphate receptor 1 8
26985316 10.1021/acsmedchemlett.5b00448 Sphingosine 1-phosphate receptor 1 8
25072873 10.1016/j.ejmech.2014.07.081 Rattus norvegicus 6
25826109 10.1021/jm502021d Mus musculus 4
15149705 10.1016/j.bmcl.2004.02.106 Rattus norvegicus 3
26985316 10.1021/acsmedchemlett.5b00448 ADMET 3
26985316 10.1021/acsmedchemlett.5b00448 Heart 2
17113298 10.1016/j.bmc.2006.10.060 Sphingosine 1-phosphate receptor 2 2
25047939 10.1016/j.bmc.2014.06.038 Sphingosine 1-phosphate receptor 1 2
15615513 10.1021/jm0492507 Sphingosine 1-phosphate receptor 1 2
17113298 10.1016/j.bmc.2006.10.060 Sphingosine 1-phosphate receptor 3 2
17113298 10.1016/j.bmc.2006.10.060 Sphingosine 1-phosphate receptor 5 2
26509640 10.1021/acs.jmedchem.5b00928 Sphingosine 1-phosphate receptor 5 2
15982878 10.1016/j.bmcl.2005.05.097 Sphingosine 1-phosphate receptor 4 2
15982878 10.1016/j.bmcl.2005.05.097 Sphingosine 1-phosphate receptor 3 2
15982878 10.1016/j.bmcl.2005.05.097 Sphingosine 1-phosphate receptor 2 2
15982878 10.1016/j.bmcl.2005.05.097 Sphingosine 1-phosphate receptor 5 2
15982878 10.1016/j.bmcl.2005.05.097 Sphingosine 1-phosphate receptor 1 2
24900589 10.1021/ml400194r Sphingosine 1-phosphate receptor 1 2

Data from ChEMBL 36 via Core Engine