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Compound Detail

CHEMBL487182

TETRAHYDROPALMATINE
🧪 Phase II
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🧪 Phase II
COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL487182
Name TETRAHYDROPALMATINE
Phase Phase II
Structure Type MOL
InChI Key AEQDJSLRWYMAQI-KRWDZBQOSA-N

Known Names

(-)-corydalis b (-)-rotundine (-)-tetrahydropalmatine Caseanine Gindarine Hyndarine L-tetrahydropalmatine Levo-tetrahydropalmatine Rotundine Tetrahydropalmatine Tetrahydropalmatine l-form Tetrahydropalmatine, (-)- +2 more
6
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
14
Known Names
1
Indications

Molecular Properties

355.4
MW (Da)
3.38
ALogP
5
HBA
0
HBD
40.2
PSA (Ų)
0.84
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C21H25NO4
MW 355.43
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.87

Indications

Cocaine-Related Disorders

Activity Summary

Ki 8 meas. best 6.91
IC50 4 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tissue factor
CHEMBL4081
 IC50 7.64 7.64 22.8 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 6.91 6.79 124.0 3
D(1B) dopamine receptor
CHEMBL1850
 Ki 6.52 6.52 305.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 6.41 6.18 388.0 2
D(2) dopamine receptor
CHEMBL217
 IC50 6.35 6.35 450.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 5.86 5.855 1371.0 2
D(1A) dopamine receptor
CHEMBL2056
 IC50 5.79 5.79 1630.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.49 4.49 32600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tissue factor IC50 = 22.78 nM 7.64 Inhibition of tissue factor procoagulant activity in LPS-stimulated human THP1 c... 23199480
D(1A) dopamine receptor Ki = 124.0 nM 6.91 Binding affinity to D1 receptor (unknown origin) assessed as inhibition constant 39038276
D(1A) dopamine receptor Ki = 153.0 nM 6.82 Displacement of [3H]SCH23390 from human 3HA-tagged dopamine D1 receptor expresse... 28214075
D(1A) dopamine receptor Ki = 231.0 nM 6.64 Displacement of [3H]SCH23390 from dopamine D1 receptor (unknown origin) expresse... 23332346
D(1B) dopamine receptor Ki = 305.0 nM 6.52 Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK293... 28214075
D(2) dopamine receptor Ki = 388.0 nM 6.41 Binding affinity to D2 receptor (unknown origin) assessed as inhibition constant 39038276
D(2) dopamine receptor IC50 = 450.0 nM 6.35 Antagonist activity at D2 receptor (unknown origin) expressed in CHOK1 cells ass... 30981605
D(2) dopamine receptor Ki = 1125.0 nM 5.95 Displacement of [3H]SCH23390 from human FLAG-tagged dopamine D2 receptor express... 28214075
D(3) dopamine receptor Ki = 1371.0 nM 5.86 Displacement of [3H]SCH23390 from human FLAG-tagged dopamine D3 receptor express... 28214075
D(3) dopamine receptor Ki = 1420.0 nM 5.85 Binding affinity to D3 receptor (unknown origin) assessed as inhibition constant 39038276
D(1A) dopamine receptor IC50 = 1630.0 nM 5.79 Antagonist activity at D1 receptor (unknown origin) expressed in CHOK1 cells ass... 30981605
Plasmodium falciparum IC50 = 32600.0 nM 4.49 Antimalarial activity against Plasmodium falciparum W2 19299148

Literature References

PubMed DOI Target Context # Activities
23332346 10.1016/j.bmc.2012.12.016 5-hydroxytryptamine receptor 2A 2
30981605 10.1016/j.bmc.2019.04.014 D(1A) dopamine receptor 2
30981605 10.1016/j.bmc.2019.04.014 D(2) dopamine receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 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
22137340 10.1016/j.bmcl.2011.11.041 Estrogen receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
8254346 10.1021/np50099a005 Plasmodium falciparum 2
23199480 10.1016/j.bmc.2012.11.002 Tissue factor 1
21295891 10.1016/j.ejmech.2011.01.016 Human immunodeficiency virus type 1 reverse transcriptase 1
39038276 10.1021/acs.jmedchem.4c00537 D(3) dopamine receptor 1
23565574 10.1021/np300882f ADMET 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
27709945 10.1021/acs.jmedchem.6b01217 Alpha-1A adrenergic receptor 1
28214075 10.1016/j.bmcl.2017.01.090 D(1A) 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

Data from ChEMBL 36 via Core Engine