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Compound Detail

CHEMBL448891

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COc1cc2c(cc1OC)[C@@H]1Cc3ccc(O)c(OC)c3CN1CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL448891
Phase Preclinical
Structure Type MOL
InChI Key DIHXHTWYVOYYDC-INIZCTEOSA-N
6
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

341.4
MW (Da)
3.07
ALogP
5
HBA
1
HBD
51.2
PSA (Ų)
0.93
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H23NO4
MW 341.41
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 1.20

Activity Summary

Ki 7 meas. best 7.3
IC50 5 meas. best 6.82
EC50 2 meas. best 6.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(1A) dopamine receptor
CHEMBL2056
 Ki 7.3 7.135 50.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 6.83 6.83 149.0 1
Tissue factor
CHEMBL4081
 IC50 6.82 6.82 152.4 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 EC50 6.72 6.72 190.0 1
D(1B) dopamine receptor
CHEMBL1850
 Ki 6.62 6.62 242.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 6.52 6.395 305.0 2
D(1A) dopamine receptor
CHEMBL2056
 EC50 5.87 5.87 1350.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 5.77 5.77 1713.0 1
D(2) dopamine receptor
CHEMBL217
 IC50 4.73 4.73 18730.0 1
D(1A) dopamine receptor
CHEMBL2056
 IC50 4.67 4.67 21270.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(1A) dopamine receptor Ki = 50.0 nM 7.3 Displacement of [3H]SCH23390 from dopamine D1 receptor (unknown origin) expresse... 23332346
D(1A) dopamine receptor Ki = 107.0 nM 6.97 Displacement of [3H]SCH23390 from human dopamine D1 receptor after 1 hr 28214075
5-hydroxytryptamine receptor 1A Ki = 149.0 nM 6.83 Displacement of [3H]8-OH-DPAT from 5-HT1A receptor (unknown origin) expressed in... 23332346
Tissue factor IC50 = 152.43 nM 6.82 Inhibition of tissue factor procoagulant activity in LPS-stimulated human THP1 c... 23199480
5-hydroxytryptamine receptor 1A EC50 = 190.0 nM 6.72 Agonist activity at 5-HT1A receptor (unknown origin) expressed in HEK293 cells a... 23332346
D(1B) dopamine receptor Ki = 242.0 nM 6.62 Displacement of [3H]SCH23390 from human dopamine D5 receptor after 1 hr 28214075
D(2) dopamine receptor Ki = 305.0 nM 6.52 Displacement of [3H]spiperone from dopamine D2 receptor (unknown origin) express... 23332346
D(2) dopamine receptor Ki = 533.0 nM 6.27 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor after 1 hr 28214075
D(1A) dopamine receptor EC50 = 1350.0 nM 5.87 Agonist activity at dopamine D1 receptor (unknown origin) expressed in HEK293 ce... 23332346
D(3) dopamine receptor Ki = 1713.0 nM 5.77 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor after 1 hr 28214075
D(2) dopamine receptor IC50 = 18730.0 nM 4.73 Antagonist activity at dopamine D2 receptor (unknown origin) expressed in HEK293... 23332346
D(1A) dopamine receptor IC50 = 21270.0 nM 4.67 Antagonist activity at dopamine D1 receptor (unknown origin) expressed in HEK293... 23332346

Literature References

PubMed DOI Target Context # Activities
23332346 10.1016/j.bmc.2012.12.016 Rattus norvegicus 12
23332346 10.1016/j.bmc.2012.12.016 D(1A) dopamine receptor 6
23332346 10.1016/j.bmc.2012.12.016 D(2) dopamine receptor 4
23332346 10.1016/j.bmc.2012.12.016 5-hydroxytryptamine receptor 1A 4
8254346 10.1021/np50099a005 Unchecked 2
8254346 10.1021/np50099a005 Plasmodium falciparum 2
23332346 10.1016/j.bmc.2012.12.016 5-hydroxytryptamine receptor 2A 2
37615114 10.1021/acs.jnatprod.3c00391 Amyloid-beta precursor protein 2
29925480 10.1016/j.bmcl.2018.06.023 Amine oxidase [flavin-containing] A 2
29925480 10.1016/j.bmcl.2018.06.023 Amine oxidase [flavin-containing] B 2
37615114 10.1021/acs.jnatprod.3c00391 No relevant target 1
37615114 10.1021/acs.jnatprod.3c00391 Unchecked 1
37615114 10.1021/acs.jnatprod.3c00391 Cholinesterase 1
37615114 10.1021/acs.jnatprod.3c00391 Acetylcholinesterase 1
28214075 10.1016/j.bmcl.2017.01.090 D(1B) dopamine receptor 1
28214075 10.1016/j.bmcl.2017.01.090 D(1A) dopamine receptor 1
28214075 10.1016/j.bmcl.2017.01.090 D(2) dopamine receptor 1
28214075 10.1016/j.bmcl.2017.01.090 D(3) dopamine receptor 1
28214075 10.1016/j.bmcl.2017.01.090 D(4) dopamine receptor 1
23199480 10.1016/j.bmc.2012.11.002 Tissue factor 1

Data from ChEMBL 36 via Core Engine