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Compound Detail

CHEMBL487387

STEPHOLIDINE
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COc1cc2c(cc1O)[C@@H]1Cc3ccc(O)c(OC)c3CN1CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL487387
Name STEPHOLIDINE
Phase Preclinical
Structure Type MOL
InChI Key JKPISQIIWUONPB-HNNXBMFYSA-N
10
Targets
32
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

327.4
MW (Da)
2.77
ALogP
5
HBA
2
HBD
62.2
PSA (Ų)
0.89
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H21NO4
MW 327.38
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 1.43

Activity Summary

Ki 26 meas. best 8.47
IC50 4 meas. best 7.91
EC50 2 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(1A) dopamine receptor
CHEMBL2056
 Ki 8.47 8.2243 3.4 7
D(1B) dopamine receptor
CHEMBL1850
 Ki 8.36 8.3 4.4 2
D(2) dopamine receptor
CHEMBL217
 Ki 7.96 6.88 11.0 7
D(1A) dopamine receptor
CHEMBL2056
 IC50 7.91 7.91 12.3 1
D(1A) dopamine receptor
CHEMBL2056
 EC50 7.64 7.64 23.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 7.63 7.448 23.4 5
D(3) dopamine receptor
CHEMBL3138
 Ki 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
 Ki 7.27 7.27 54.0 1
D(2) dopamine receptor
CHEMBL217
 IC50 6.98 6.17 105.4 2
Tissue factor
CHEMBL4081
 IC50 6.98 6.98 104.6 1
D(4) dopamine receptor
CHEMBL219
 Ki 5.84 5.635 1453.0 2
Alpha-1A adrenergic receptor
CHEMBL319
 Ki 5.65 5.65 2238.7 1
D(1A) dopamine receptor
CHEMBL265
 EC50 4.39 4.39 41100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 54.0 mL.min-1.kg-1 Rattus norvegicus
T1/2 0.1067 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(1A) dopamine receptor Ki = 3.4 nM 8.47 Displacement of [3H]SCH23390 from dopamine D1 receptor (unknown origin) expresse... 23332346
D(1B) dopamine receptor Ki = 4.4 nM 8.36 Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in CHO ce... 19744859
D(1A) dopamine receptor Ki = 5.1 nM 8.29 Binding affinity to D1 receptor (unknown origin) assessed as inhibition constant 39038276
D(1B) dopamine receptor Ki = 5.8 nM 8.24 Binding affinity to D5 receptor (unknown origin) assessed as inhibition constant 39038276
D(1A) dopamine receptor Ki = 5.9 nM 8.23 Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in CHO ce... 19744859
D(1A) dopamine receptor Ki = 5.9 nM 8.23 Displacement of [3H]SCH23390 from human D1 receptor expressed in HEKT cell membr... 27688181
D(1A) dopamine receptor Ki = 5.9 nM 8.23 Displacement of [3H]SCH-23390 from human dopamine D1 receptor assessed as inhibi... 37421373
D(1A) dopamine receptor Ki = 6.23 nM 8.21 Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in HEK293... 22748706
D(2) dopamine receptor Ki = 11.0 nM 7.96 Displacement of [3H]spiperone from dopamine D2 receptor (unknown origin) express... 23332346
D(2) dopamine receptor Ki = 11.6 nM 7.94 Binding affinity to D2 receptor (unknown origin) assessed as inhibition constant 39038276
D(1A) dopamine receptor Ki = 12.29 nM 7.91 Displacement of [3H]SCH23390 from D1 receptor (unknown origin) transfected in HE... 25308766
D(1A) dopamine receptor IC50 = 12.29 nM 7.91 Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in HEK293... 22748706
D(1A) dopamine receptor EC50 = 23.0 nM 7.64 Agonist activity at D1 receptor (unknown origin) after 40 mins by [35S]GTP-gamma... 25308766
D(3) dopamine receptor Ki = 23.4 nM 7.63 Binding affinity to D3 receptor (unknown origin) assessed as inhibition constant 39038276
D(3) dopamine receptor Ki = 30.0 nM 7.52 Displacement of [3H]spiperone from rat dopamine D3 receptor expressed in CHO cel... 19744859
D(3) dopamine receptor Ki = 30.0 nM 7.52 Binding affinity to dopamine D3 receptor (unknown origin) by PDSP assay 27032890
D(3) dopamine receptor Ki = 30.0 nM 7.52 Displacement of [3H]N-methylspiperone from human D3 receptor expressed in HEKT c... 27688181
D(3) dopamine receptor Ki = 30.0 nM 7.52 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor assessed a... 37421373
Unchecked Ki = 54.0 nM 7.27 Binding affinity to sigma2 receptor (unknown origin) by PDSP assay 27032890
D(2) dopamine receptor Ki = 56.17 nM 7.25 Displacement of [3H]Spiprone from human dopamine D2 receptor expressed in HEK293... 22748706

Literature References

PubMed DOI Target Context # Activities
22748706 10.1016/j.bmc.2012.05.057 D(1A) dopamine receptor 6
37421373 10.1021/acs.jmedchem.3c00976 ADMET 5
25308766 10.1016/j.bmc.2014.09.024 D(2) dopamine receptor 3
37421373 10.1021/acs.jmedchem.3c00976 Unchecked 3
25308766 10.1016/j.bmc.2014.09.024 D(1A) dopamine receptor 3
19744859 10.1016/j.bmc.2009.08.028 D(1A) dopamine receptor 3
19744859 10.1016/j.bmc.2009.08.028 D(2) dopamine receptor 3
22748706 10.1016/j.bmc.2012.05.057 D(2) dopamine receptor 2
23332346 10.1016/j.bmc.2012.12.016 5-hydroxytryptamine receptor 2A 2
23332346 10.1016/j.bmc.2012.12.016 D(1A) dopamine receptor 2
23332346 10.1016/j.bmc.2012.12.016 D(2) dopamine receptor 2
23332346 10.1016/j.bmc.2012.12.016 5-hydroxytryptamine receptor 1A 2
25308766 10.1016/j.bmc.2014.09.024 D(3) dopamine receptor 2
27688181 10.1016/j.ejmech.2016.09.036 D(3) dopamine receptor 2
27688181 10.1016/j.ejmech.2016.09.036 D(1A) dopamine receptor 2
27688181 10.1016/j.ejmech.2016.09.036 D(2) dopamine receptor 2
39038276 10.1021/acs.jmedchem.4c00537 D(4) dopamine receptor 1
22748706 10.1016/j.bmc.2012.05.057 5-hydroxytryptamine receptor 2A 1
22748706 10.1016/j.bmc.2012.05.057 5-hydroxytryptamine receptor 1A 1
11087586 10.1021/np000176e HepG2 1

Data from ChEMBL 36 via Core Engine