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Compound Detail

CHEMBL549472

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CCCCCCCCC[C@H](O)CC(=O)CCc1ccc(O)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL549472
Phase Preclinical
Structure Type MOL
InChI Key AIULWNKTYPZYAN-SFHVURJKSA-N
9
Targets
16
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

350.5
MW (Da)
4.79
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.47
QED
0
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H34O4
MW 350.50
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness 1.28

Activity Summary

IC50 15 meas. best 5.7
Ki 1 meas. best 5.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 2C8
CHEMBL3721
 IC50 5.7 5.7 2000.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 5.43 5.43 3740.0 1
Cytochrome P450 2B6
CHEMBL4729
 IC50 5.37 5.37 4300.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 5.18 5.025 6600.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 5.15 4.7725 7100.0 4
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.12 4.955 7500.0 2
No relevant target
CHEMBL2362975
 IC50 4.92 4.92 12000.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.26 4.26 54900.0 1
Cytochrome P450 2A6
CHEMBL5282
 IC50 4.01 4.01 98300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 2C8 IC50 = 2000.0 nM 5.7 Inhibition of CYP2C8 in human liver microsomes using amodiaquin as substrate pre... 28274629
5-hydroxytryptamine receptor 1A Ki = 3740.0 nM 5.43 Displacement of [3H]8-OH-DPAT from 5HT1A receptor expressed in HEK293 cells afte... 20363635
Cytochrome P450 2B6 IC50 = 4300.0 nM 5.37 Inhibition of CYP2B6 in human liver microsomes using bupropion as substrate prei... 28274629
Cytochrome P450 2C19 IC50 = 6600.0 nM 5.18 Inhibition of CYP2C19 in human liver microsomes using (S)-mephenytoin as substra... 28274629
Cytochrome P450 3A4 IC50 = 7100.0 nM 5.15 Inhibition of CYP3A4 in human liver microsomes using testosterone as substrate p... 28274629
Cytochrome P450 2C9 IC50 = 7500.0 nM 5.12 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre... 28274629
No relevant target IC50 = 12000.0 nM 4.92 Antioxidant activity assessed as DPPH radical scavenging activity 22246389
Cytochrome P450 2C19 IC50 = 13600.0 nM 4.87 Inhibition of recombinant human CYP2C19 expressed in baculosomes using Vivid EOM... 28274629
Cytochrome P450 2C9 IC50 = 16300.0 nM 4.79 Inhibition of recombinant human CYP2C9 expressed in baculosomes using Vivid OOMR... 28274629
Cytochrome P450 3A4 IC50 = 20800.0 nM 4.68 Inhibition of recombinant human CYP3A4 expressed in baculosomes using Vivid BOMC... 28274629
Cytochrome P450 3A4 IC50 = 21800.0 nM 4.66 Inhibition of recombinant human CYP3A4 expressed in baculosomes using Vivid DBOM... 28274629
Cytochrome P450 3A4 IC50 = 24900.0 nM 4.6 Inhibition of recombinant human CYP3A4 expressed in baculosomes using Vivid BOMR... 28274629
Cytochrome P450 2D6 IC50 = 54900.0 nM 4.26 Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substra... 28274629
Cytochrome P450 2A6 IC50 = 98300.0 nM 4.01 Inhibition of CYP2A6 in human liver microsomes using Coumarin as substrate prein... 28274629

Literature References

PubMed DOI Target Context # Activities
19271742 10.1021/np800555y RBL-2H3 9
20363635 10.1016/j.bmc.2010.02.062 5-hydroxytryptamine receptor 1A 5
28274629 10.1016/j.bmcl.2017.02.047 Cytochrome P450 3A4 4
31744675 10.1016/j.bmcl.2019.126815 Aldo-keto reductase family 1 member B1 3
19271742 10.1021/np800555y ADMET 2
20363635 10.1016/j.bmc.2010.02.062 Caco-2 2
28274629 10.1016/j.bmcl.2017.02.047 Cytochrome P450 2C9 2
28274629 10.1016/j.bmcl.2017.02.047 Cytochrome P450 2C19 2
20363635 10.1016/j.bmc.2010.02.062 ATP-dependent translocase ABCB1 1
22246389 10.1124/dmd.111.043331 No relevant target 1
28231520 10.1016/j.ejmech.2017.02.005 Rodentolepis nana 1
28274629 10.1016/j.bmcl.2017.02.047 Cytochrome P450 2B6 1
28274629 10.1016/j.bmcl.2017.02.047 Cytochrome P450 2C8 1
28274629 10.1016/j.bmcl.2017.02.047 Cytochrome P450 2A6 1
28274629 10.1016/j.bmcl.2017.02.047 Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine