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Compound Detail

CHEMBL574645

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OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCCCCOCC12CC3CC(CC(C3)C1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL574645
Phase Preclinical
Structure Type MOL
InChI Key XVYLNHVEAOOEGI-FAIWKWDXSA-N
14
Targets
39
Activities
1
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

397.6
MW (Da)
1.15
ALogP
6
HBA
4
HBD
93.4
PSA (Ų)
0.44
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 C22H39NO5
MW 397.56
Aromatic Rings 0
Heavy Atoms 28
NP-Likeness 0.75

Activity Summary

IC50 39 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-glucosidase
CHEMBL3761
 IC50 9.52 8.93 0.3 8
CuFi-1
CHEMBL4513124
 IC50 8.73 8.73 1.8 1
Ceramide glucosyltransferase
CHEMBL2063
 IC50 7.05 6.3186 90.0 7
Lysosomal acid glucosylceramidase
CHEMBL2179
 IC50 7.0 6.85 100.0 2
Unchecked
CHEMBL612545
 IC50 6.89 6.1486 130.0 7
Ceramide glucosyltransferase
CHEMBL6013
 IC50 6.7 6.7 200.0 2
Lysosomal alpha-glucosidase
CHEMBL2608
 IC50 6.4 6.4 400.0 2
Sucrase-isomaltase
CHEMBL1667666
 IC50 6.3 6.3 500.0 1
Sucrase-isomaltase, intestinal
CHEMBL2748
 IC50 6.3 6.26 500.0 2
Maltase-glucoamylase
CHEMBL2074
 IC50 5.52 5.46 3000.0 2
Lysosomal alpha-glucosidase
CHEMBL1667668
 IC50 5.4 5.4 4000.0 1
Glycogen debranching enzyme
CHEMBL5272
 IC50 5.0 5.0 10000.0 1
Lactase/phlorizin hydrolase
CHEMBL1075131
 IC50 4.46 4.46 35000.0 2
Beta-galactosidase
CHEMBL1667667
 IC50 4.46 4.46 35000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3400.0 ng.hr.mL-1 Rattus norvegicus
AUC 340.0 ng.hr.mL-1 Rattus norvegicus
Cmax 3018.41 nM Rattus norvegicus
Cmax 301.84 nM Rattus norvegicus
F 41.0 % Rattus norvegicus
MRT 4.2 hr Rattus norvegicus
T1/2 4.2 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-glucosidase IC50 = 0.3 nM 9.52 Inhibition of non-lysosomal glucosylceramidase in cultured melanoma cells 21354674
Beta-glucosidase IC50 = 1.0 nM 9.0 Inhibition of human GBA2 19853441
Beta-glucosidase IC50 = 1.0 nM 9.0 Inhibition of glucosylceramidase 2 from spleen of patient with gaucher's disease... 24900342
Beta-glucosidase IC50 = 1.0 nM 9.0 Inhibition of recombinant GBA2 preincubated with compound for 30 mins using 4-me... 24900289
Beta-glucosidase IC50 = 1.0 nM 9.0 Inhibition of GBA2 by HPLC 20000679
CuFi-1 IC50 = 1.84 nM 8.73 Anti-inflammatory activity in human CuFi1 cells assessed as reduction in Pseudom... 31075609
Beta-glucosidase IC50 = 2.0 nM 8.7 Inhibition of non-lysosomal glucosylceramidase 21354674
Beta-glucosidase IC50 = 2.0 nM 8.7 Inhibition of GBA2 (unknown origin) 25250725
Beta-glucosidase IC50 = 3.0 nM 8.52 Inhibition of NLGase in human SH-SY5Y cells using MUG-Gluc as fluorogenic substr... 31075609
Ceramide glucosyltransferase IC50 = 90.0 nM 7.05 Inhibition of GCS assessed as amount of UDP-glucose consumed during enzyme-catal... 21974949
Ceramide glucosyltransferase IC50 = 90.0 nM 7.05 Inhibition of GCS assessed as amount of UDP glucose after 3 hrs by Fluorometry a... 22497444
Ceramide glucosyltransferase IC50 = 90.0 nM 7.05 Inhibition of glucosylceramide synthase (unknown origin) -
Lysosomal acid glucosylceramidase IC50 = 100.0 nM 7.0 Inhibition of GBA1 (unknown origin) using beta-D-[1-14C]glucocerebroside assesse... 25250725
Unchecked IC50 = 130.0 nM 6.89 Inhibition of rice alpha glucosidase 19853441
Ceramide glucosyltransferase IC50 = 150.0 nM 6.82 Inhibition of GCS by cell-based assay 20000679
Ceramide glucosyltransferase IC50 = 200.0 nM 6.7 Inhibition of glucosylceramide synthase (unknown origin) assessed as catabolism ... 25250725
Unchecked IC50 = 200.0 nM 6.7 Inhibition of recombinant glucosylceramidase 1 using 4-methylumbelliferyl-B-gluc... 24900342
Ceramide glucosyltransferase IC50 = 200.0 nM 6.7 Inhibition of glucosylceramide synthase in mouse RAW cells preincubated for 15 m... 24900342
Lysosomal acid glucosylceramidase IC50 = 200.0 nM 6.7 Inhibition of recombinant GBA1 preincubated with compound for 30 mins using 4-me... 24900289
Unchecked IC50 = 200.0 nM 6.7 Inhibition of GBA1 by HPLC 20000679

Literature References

PubMed DOI Target Context # Activities
20000679 10.1021/jm901281m Rattus norvegicus 11
20000679 10.1021/jm901281m Mus musculus 9
19853441 10.1016/j.bmcl.2009.10.022 Unchecked 5
22497444 10.1021/jm300122u Mus musculus 4
31075609 10.1016/j.ejmech.2019.04.061 CuFi-1 3
21974949 10.1016/j.bmcl.2011.09.037 Ceramide glucosyltransferase 2
22497444 10.1021/jm300122u Ceramide glucosyltransferase 2
21354674 10.1016/j.ejmech.2011.01.047 Beta-glucosidase 2
31075609 10.1016/j.ejmech.2019.04.061 Beta-glucosidase 2
31075609 10.1016/j.ejmech.2019.04.061 Lysosomal acid glucosylceramidase 2
20000679 10.1021/jm901281m Beta-glucosidase 1
20000679 10.1021/jm901281m Glycogen debranching enzyme 1
20000679 10.1021/jm901281m Unchecked 1
24900289 10.1021/ml100192b Lysosomal alpha-glucosidase 1
24900289 10.1021/ml100192b Beta-galactosidase 1
20000679 10.1021/jm901281m Maltase-glucoamylase 1
20000679 10.1021/jm901281m Sucrase-isomaltase, intestinal 1
24900289 10.1021/ml100192b Lysosomal acid glucosylceramidase 1
20000679 10.1021/jm901281m Ceramide glucosyltransferase 1
19853441 10.1016/j.bmcl.2009.10.022 Lysosomal alpha-glucosidase 1

Data from ChEMBL 36 via Core Engine