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Compound Detail

CHEMBL145233

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C/C(=C\COP(=O)(O)OP(=O)(O)O)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL145233
Phase Preclinical
Structure Type MOL
InChI Key MDSIZRKJVDMQOQ-GORDUTHDSA-N
2
Targets
33
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

262.1
MW (Da)
0.15
ALogP
5
HBA
4
HBD
133.5
PSA (Ų)
0.39
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C5H12O8P2
MW 262.09
Aromatic Rings 0
Heavy Atoms 15
NP-Likeness 2.17

Activity Summary

EC50 20 meas. best 10.22
IC50 10 meas. best 6.3
Kd 3 meas. best 5.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Butyrophilin subfamily 3 member A1
CHEMBL4105758
 EC50 10.22 9.4163 0.1 8
Unchecked
CHEMBL612545
 EC50 10.22 8.4817 0.1 12
Unchecked
CHEMBL612545
 IC50 6.3 6.3 500.0 1
Butyrophilin subfamily 3 member A1
CHEMBL4105758
 Kd 5.81 5.5267 1540.0 3
Butyrophilin subfamily 3 member A1
CHEMBL4105758
 IC50 5.34 4.8633 4560.0 9

Pharmacokinetic Data

Parameter Value Units Species
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Butyrophilin subfamily 3 member A1 EC50 = 0.06 nM 10.22 Binding affinity to BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells 32930595
Butyrophilin subfamily 3 member A1 EC50 = 0.06 nM 10.22 Binding affinity to butyrophilin 3A1 in human Vgamma9/Vdelta2 T-cells assessed a... 29457898
Unchecked EC50 = 0.06 nM 10.22 Induction of Vgamma9Vdelta2 T cells (unknown origin) proliferation assessed as i... 39026632
Unchecked EC50 = 0.084 nM 10.08 Mean effective concentration of compound was determined in stimulating Vgamma9 /... 12657258
Butyrophilin subfamily 3 member A1 EC50 = 0.145 nM 9.84 Binding affinity to BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assesse... 32930595
Unchecked EC50 = 0.145 nM 9.84 Induction of Vgamma9Vdelta2 T cell activation in human PBMC cells assessed as CD... 39026632
Unchecked EC50 = 0.181 nM 9.74 Mean effective concentration of compound was determined in stimulating Vgamma9 /... 12657258
Unchecked EC50 = 0.3 nM 9.52 Effective concentration range of compound was determined in stimulating Vgamma9 ... 12657258
Unchecked EC50 = 0.39 nM 9.41 Agonist activity at human Vgamma9Vdelta2 receptor expressed in T cells assessed ... 18303828
Butyrophilin subfamily 3 member A1 EC50 = 0.51 nM 9.29 Activation of BTN3A1 in human Vgamma9Vdelta2 T cells assessed as induction of in... 28218845
Butyrophilin subfamily 3 member A1 EC50 = 0.51 nM 9.29 Binding affinity to BTN3A1 in human PBMC assessed as stimulation of Vgamma9 Vdel... 30199251
Butyrophilin subfamily 3 member A1 EC50 = 0.51 nM 9.29 Activation of BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as i... 31268699
Unchecked EC50 = 0.51 nM 9.29 Induction of Vgamma9Vdelta2 T cell proliferation in human PBMC cells incubated f... 37934915
Unchecked EC50 = 1.0 nM 9.0 Effective concentration range of compound was determined in stimulating Vgamma9 ... 12657258
Unchecked EC50 = 1.0 nM 9.0 Induction of cell proliferation of human PBMC into human Vgamma9Vdelta2 T cells ... 39029338
Butyrophilin subfamily 3 member A1 EC50 = 1.6 nM 8.8 Activation of BTN3A1 in human Vgamma9Vdelta2 T cells assessed as induction of T ... 28218845
Butyrophilin subfamily 3 member A1 EC50 = 4.2 nM 8.38 Activation of BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as i... 31268699
Unchecked IC50 = 500.0 nM 6.3 Toxicity in human Vgamma9/Vdelta2 T cells treated for 72 hrs measured on day 11 ... 28218845
Butyrophilin subfamily 3 member A1 Kd = 1540.0 nM 5.81 Binding affinity to C-terminal 6His-tagged BTN3A1 full interaction domain (unkno... 31268699
Unchecked EC50 = 4000.0 nM 5.4 Induction of Vgamma9Vdelta2 T cell activation in human PBMC cells incubated for ... 39026632

Literature References

PubMed DOI Target Context # Activities
31268699 10.1021/acs.jmedchem.9b00825 Butyrophilin subfamily 3 member A1 16
12657258 10.1016/s0960-894x(03)00138-0 Unchecked 9
18303828 10.1021/jm701101g No relevant target 5
18303828 10.1021/jm701101g NON-PROTEIN TARGET 4
32912439 10.1016/j.bmc.2020.115666 Unchecked 4
32930595 10.1021/acs.jmedchem.0c01232 Butyrophilin subfamily 3 member A1 4
28218845 10.1021/acs.jmedchem.6b00965 Butyrophilin subfamily 3 member A1 4
39029338 10.1016/j.ejmech.2024.116673 Butyrophilin subfamily 3 member A1 3
39026632 10.1039/d4md00208c Unchecked 3
29457898 10.1021/acs.jmedchem.7b01824 Butyrophilin subfamily 3 member A1 3
30199251 10.1021/acs.jmedchem.8b00655 Butyrophilin subfamily 3 member A1 2
28218845 10.1021/acs.jmedchem.6b00965 Unchecked 2
18303828 10.1021/jm701101g Rattus norvegicus 2
37934915 10.1021/acs.jmedchem.3c01358 Unchecked 2
29457898 10.1021/acs.jmedchem.7b01824 Unchecked 1
28218845 10.1021/acs.jmedchem.6b00965 K562 1
32930595 10.1021/acs.jmedchem.0c01232 T-24 1
32930595 10.1021/acs.jmedchem.0c01232 ADMET 1
39029338 10.1016/j.ejmech.2024.116673 Unchecked 1
18303828 10.1021/jm701101g Unchecked 1

Data from ChEMBL 36 via Core Engine