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Compound Detail

CHEMBL3806205

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CCCCCC[C@@H]1CCc2cc([C@H]3CC[C@](N)(COP(=O)(O)O)C3)ccc2C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3806205
Phase Preclinical
Structure Type MOL
InChI Key BWKSEIHXZRSETR-VOQZNFBZSA-N
5
Targets
25
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

409.5
MW (Da)
4.84
ALogP
3
HBA
3
HBD
92.8
PSA (Ų)
0.40
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H36NO4P
MW 409.51
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness 1.11

Activity Summary

EC50 20 meas. best 9.96
IC50 5 meas. best 11.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 IC50 11.0 11.0 0.0 3
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 EC50 9.96 8.946 0.1 10
Unchecked
CHEMBL612545
 IC50 8.6 8.6 2.5 2
Mus musculus
CHEMBL375
 EC50 8.1 8.1 7.9 2
Sphingosine 1-phosphate receptor 4
CHEMBL3230
 EC50 7.98 7.98 10.5 3
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 EC50 7.97 7.97 10.7 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 1883.75 ng.hr.mL-1 Mus musculus
AUC 2129.45 ng.hr.mL-1 Mus musculus
Cmax 49.0 nM Mus musculus
MRT 88.0 hr Mus musculus
T1/2 56.0 hr Mus musculus
Tmax 24.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingosine 1-phosphate receptor 1 IC50 = 0.01 nM 11.0 Displacement of [33P]-SIP from human recombinant S1P1 expressed in CHO cell memb... 30785748
Sphingosine 1-phosphate receptor 1 IC50 = 0.01 nM 11.0 Displacement of [33P]-SIP from human recombinant S1P1 expressed in CHO cell memb... 33492963
Sphingosine 1-phosphate receptor 1 IC50 = 0.01 nM 11.0 Displacement of 33-P-S1P from from human S1P receptor expressed in CHO cell memb... 26985316
Sphingosine 1-phosphate receptor 1 EC50 = 0.11 nM 9.96 Agonist activity at human recombinant C-terminal GFP-fused S1P1 expressed in CHO... 30785748
Sphingosine 1-phosphate receptor 1 EC50 = 0.11 nM 9.96 Agonist activity at human recombinant C-terminal GFP-fused S1P1 expressed in CHO... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 0.114 nM 9.94 Agonist activity at human S1P1 receptor expressed in CHO cells co-expressing GFP... 26985316
Sphingosine 1-phosphate receptor 1 EC50 = 0.9 nM 9.05 Agonist activity at recombinant human S1P1 expressed in CHO cell membranes asses... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 0.9 nM 9.05 Agonist activity at human recombinant S1P1 expressed in CHO cell membranes asses... 30785748
Sphingosine 1-phosphate receptor 1 EC50 = 0.901 nM 9.04 Agonist activity at human S1P1 receptor by GTPgammaS binding assay 26985316
Unchecked IC50 = 2.5 nM 8.6 Antimigratory activity against human T cells assessed as inhibition of S1P-induc... 30785748
Unchecked IC50 = 2.5 nM 8.6 Antimigratory activity against human T cells assessed as inhibition of S1P-induc... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 6.4 nM 8.19 Agonist activity at human S1P1 in HLE cell membranes incubated for 45 mins by sc... 28002964
Mus musculus EC50 = 7.9 nM 8.1 Induction of lymphopenia in orally dosed Balb/c mouse assessed as reduction of c... 28002964
Mus musculus EC50 = 7.9 nM 8.1 Reduction of blood lymphocyte level in BALB/c mouse administered through oral ga... 26985316
Sphingosine 1-phosphate receptor 1 EC50 = 8.2 nM 8.09 Agonist activity at human recombinant S1P1 expressed in CHO cells assessed as st... 30785748
Sphingosine 1-phosphate receptor 1 EC50 = 8.2 nM 8.09 Agonist activity at human recombinant S1P1 expressed in CHO cells assessed as st... 33492963
Sphingosine 1-phosphate receptor 1 EC50 = 8.16 nM 8.09 Agonist activity at human S1P1 receptor expressed in CHO cells assessed as ERK p... 26985316
Sphingosine 1-phosphate receptor 4 EC50 = 10.5 nM 7.98 Agonist activity at human S1P4 receptor by GTPgammaS binding assay 26985316
Sphingosine 1-phosphate receptor 4 EC50 = 10.5 nM 7.98 Agonist activity at recombinant human S1P4 expressed in CHO cell membranes asses... 33492963
Sphingosine 1-phosphate receptor 4 EC50 = 10.5 nM 7.98 Agonist activity at human recombinant S1P4 expressed in CHO cell membranes asses... 30785748

Literature References

PubMed DOI Target Context # Activities
30785748 10.1021/acs.jmedchem.8b01695 Sphingosine 1-phosphate receptor 1 10
26985316 10.1021/acsmedchemlett.5b00448 Sphingosine 1-phosphate receptor 1 8
26985316 10.1021/acsmedchemlett.5b00448 Mus musculus 8
33492963 10.1021/acs.jmedchem.0c01109 Sphingosine 1-phosphate receptor 1 8
26985316 10.1021/acsmedchemlett.5b00448 Heart 4
28002964 10.1021/acs.jmedchem.6b01433 Cerebellum 3
26985316 10.1021/acsmedchemlett.5b00448 Sphingosine 1-phosphate receptor 3 2
32944145 10.1021/acsmedchemlett.0c00333 Cardiac muscle cell 2
28002964 10.1021/acs.jmedchem.6b01433 Sphingosine 1-phosphate receptor 1 2
28002964 10.1021/acs.jmedchem.6b01433 Sphingosine 1-phosphate receptor 3 2
30785748 10.1021/acs.jmedchem.8b01695 Unchecked 1
30785748 10.1021/acs.jmedchem.8b01695 Sphingosine 1-phosphate receptor 4 1
30785748 10.1021/acs.jmedchem.8b01695 Sphingosine 1-phosphate receptor 3 1
33492963 10.1021/acs.jmedchem.0c01109 Unchecked 1
33492963 10.1021/acs.jmedchem.0c01109 Sphingosine 1-phosphate receptor 5 1
33492963 10.1021/acs.jmedchem.0c01109 Sphingosine 1-phosphate receptor 4 1
33492963 10.1021/acs.jmedchem.0c01109 Sphingosine 1-phosphate receptor 3 1
28002964 10.1021/acs.jmedchem.6b01433 Mus musculus 1
26985316 10.1021/acsmedchemlett.5b00448 ADMET 1
26985316 10.1021/acsmedchemlett.5b00448 Sphingosine 1-phosphate receptor 5 1

Data from ChEMBL 36 via Core Engine