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Compound Detail

CHEMBL228082

GLAUCINE
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COc1cc2c(cc1OC)-c1c(OC)c(OC)cc3c1[C@H](C2)N(C)CC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL228082
Name GLAUCINE
Phase Preclinical
Structure Type MOL
InChI Key RUZIUYOSRDWYQF-HNNXBMFYSA-N
15
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

355.4
MW (Da)
3.47
ALogP
5
HBA
0
HBD
40.2
PSA (Ų)
0.84
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H25NO4
MW 355.43
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 1.18

Activity Summary

IC50 8 meas. best 5.52
Ki 8 meas. best 7.37

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 7.37 7.37 43.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.92 6.92 119.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 6.77 6.77 171.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.48 6.48 328.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.01 6.01 966.0 2
D(2) dopamine receptor
CHEMBL339
 Ki 5.55 5.55 2800.0 1
D(1A) dopamine receptor
CHEMBL265
 Ki 5.54 5.54 2900.0 1
D(2) dopamine receptor
CHEMBL217
 IC50 5.52 5.52 3020.0 1
D(1A) dopamine receptor
CHEMBL2056
 IC50 5.41 5.41 3900.0 1
Coxsackievirus B1
CHEMBL612677
 IC50 4.68 4.68 21000.0 1
ADMET
CHEMBL612558
 IC50 4.66 4.66 22000.0 1
Echovirus E13
CHEMBL613203
 IC50 4.22 4.22 60000.0 1
Poliovirus 1
CHEMBL613556
 IC50 4.22 4.22 60000.0 1
Protein tyrosine phosphatase receptor type C-associated protein
CHEMBL4806
 IC50 4.06 4.06 88000.0 1
Unchecked
CHEMBL612545
 IC50 4.01 4.01 96900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 7 Ki = 43.0 nM 7.37 Displacement of [3H]LSD from human recombinant 5-HT7 receptor expressed in HEK c... 25695425
5-hydroxytryptamine receptor 2B Ki = 119.0 nM 6.92 Displacement of [3H]LSD from 5-HT2B receptor (unknown origin) assessed as inhibi... 36001775
5-hydroxytryptamine receptor 1A Ki = 171.0 nM 6.77 Displacement of [3H]Way100635 from human recombinant 5-HT1A receptor expressed i... 25695425
5-hydroxytryptamine receptor 2C Ki = 328.0 nM 6.48 Displacement of [3H]Mesulergine from 5-HT2C receptor (unknown origin) assessed a... 36001775
5-hydroxytryptamine receptor 2A Ki = 966.0 nM 6.01 Displacement of [3H]ketanserin from human recombinant 5-HT2A receptor expressed ... 25695425
5-hydroxytryptamine receptor 2A Ki = 966.0 nM 6.01 Displacement of [3H]Ketanserin from 5-HT2A receptor (unknown origin) assessed as... 36001775
D(2) dopamine receptor Ki = 2800.0 nM 5.55 Displacement of [3H]raclopride from rat dopamine D2 receptor 17228858
D(1A) dopamine receptor Ki = 2900.0 nM 5.54 Displacement of [3H]SCH-23390 from rat dopamine D1 receptor 17228858
D(2) dopamine receptor IC50 = 3020.0 nM 5.52 Antagonist activity at D2 receptor (unknown origin) 39038276
D(1A) dopamine receptor IC50 = 3900.0 nM 5.41 Antagonist activity at D1 receptor (unknown origin) 39038276
Coxsackievirus B1 IC50 = 21000.0 nM 4.68 Antiviral activity against Coxsackievirus B1 in human FL cells 18590964
ADMET IC50 = 22000.0 nM 4.66 Cytotoxicity against human HeLa Ohio-1 cells 18590964
Echovirus E13 IC50 = 60000.0 nM 4.22 Antiviral activity against Echovirus 13 in human FL cells 18590964
Poliovirus 1 IC50 = 60000.0 nM 4.22 Antiviral activity against Poliovirus type 1 Lsc-2ab in human FL cells 18590964
Protein tyrosine phosphatase receptor type C-associated protein IC50 = 88000.0 nM 4.06 In vitro inhibitory activity against recombinant CD45 protein tyrosine phosphata... -
Unchecked IC50 = 96900.0 nM 4.01 Inhibition of Clostridium perfringens neuraminidase 4-methylumbelliferyl-alpha-D... 25277281

Literature References

PubMed DOI Target Context # Activities
18590964 10.1016/j.bmc.2008.06.010 Radical scavenging activity 6
17228858 10.1021/jm060959i Rattus norvegicus 4
18590964 10.1016/j.bmc.2008.06.010 Unchecked 4
25695425 10.1021/np500893h Unchecked 2
28675836 10.1016/j.ejmech.2017.06.047 Unchecked 2
36001775 10.1021/acs.jnatprod.2c00365 Unchecked 2
25277281 10.1016/j.bmc.2014.09.004 Neuraminidase 2
18590964 10.1016/j.bmc.2008.06.010 ADMET 2
18590964 10.1016/j.bmc.2008.06.010 Echovirus E13 1
25695425 10.1021/np500893h 5-hydroxytryptamine receptor 2A 1
39038276 10.1021/acs.jmedchem.4c00537 D(2) dopamine receptor 1
18590964 10.1016/j.bmc.2008.06.010 Coxsackievirus B1 1
18590964 10.1016/j.bmc.2008.06.010 rhinovirus B14 1
18590964 10.1016/j.bmc.2008.06.010 Poliovirus 1 1
- 10.1016/0960-894X(95)00250-W Protein tyrosine phosphatase receptor type C-associated protein 1
10978214 10.1021/np990639k Staphylococcus aureus 1
17228858 10.1021/jm060959i D(2) dopamine receptor 1
17228858 10.1021/jm060959i D(1A) dopamine receptor 1
17081761 10.1016/j.bmc.2006.10.034 B-cell 1
17081761 10.1016/j.bmc.2006.10.034 T-cell 1

Data from ChEMBL 36 via Core Engine