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Compound Detail

CHEMBL93240

METITEPINE
🧪 Phase II
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🧪 Phase II
CSc1ccc2c(c1)C(N1CCN(C)CC1)Cc1ccccc1S2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL93240
Name METITEPINE
Phase Phase II
Structure Type MOL
InChI Key RLJFTICUTYVZDG-UHFFFAOYSA-N

Known Names

Methiotepin Methiothepine Metitepina Metitepine NSC-759875 RO 8-6837 RO-8-6837
15
Targets
61
Activities
3
Assay Types
1
PK Parameters
20
Publications
7
Known Names

Molecular Properties

356.6
MW (Da)
4.40
ALogP
4
HBA
0
HBD
6.5
PSA (Ų)
0.74
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

Natural Product
USAN Stem -pine

Extended Properties

Molecular Formula C20H24N2S2
MW 356.56
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.73

Activity Summary

Ki 38 meas. best 9.52
IC50 12 meas. best 9.09
EC50 11 meas. best 9.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 9.52 9.0017 0.3 12
5-hydroxytryptamine receptor 2C
CHEMBL225
 EC50 9.42 9.42 0.4 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 9.4 9.4 0.4 1
D(2) dopamine receptor
CHEMBL339
 Ki 9.4 9.4 0.4 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 9.26 8.8433 0.5 9
5-hydroxytryptamine receptor 7
CHEMBL3155
 EC50 9.22 9.22 0.6 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 IC50 9.09 8.41 0.8 5
5-hydroxytryptamine receptor 5A
CHEMBL3426
 Ki 9.0 8.125 1.0 4
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 8.7 8.7 2.0 1
D(1A) dopamine receptor
CHEMBL265
 Ki 8.7 8.7 2.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 8.66 7.984 2.2 5
5-hydroxytryptamine receptor 6
CHEMBL3371
 IC50 8.62 8.028 2.4 5
5-hydroxytryptamine receptor 6
CHEMBL3372
 Ki 8.42 7.4733 3.8 3
5-hydroxytryptamine receptor 7
CHEMBL3223
 Ki 8.4 8.4 4.0 1
G protein-coupled receptor
CHEMBL3559679
 EC50 6.48 6.48 330.0 2
G-protein coupled receptor homolog US28
CHEMBL4259
 EC50 6.46 6.455 350.0 2
Unchecked
CHEMBL612545
 EC50 6.46 6.01 350.0 3
Unchecked
CHEMBL612545
 IC50 6.39 5.96 410.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.58 5.505 2663.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.5167 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 6 Ki = 0.3 nM 9.52 Displacement of [3H]LSD from human 5HT6 receptor expressed in CHO-K1 membrane in... 34530376
5-hydroxytryptamine receptor 6 Ki = 0.3 nM 9.52 Displacement of [3H]-LSD from human 5HT6R expressed in CHO-K1 cell membranes inc... 34461507
5-hydroxytryptamine receptor 2C EC50 = 0.38 nM 9.42 Antagonist activity at serotonin-activated human recombinant 5HT-2C receptor exp... 23537943
D(2) dopamine receptor Ki = 0.3981 nM 9.4 Half-maximal inhibition of [3H]spiperone binding to Dopamine receptor D2 in rat ... 11784139
5-hydroxytryptamine receptor 2A Ki = 0.3981 nM 9.4 Half-maximal inhibition of [3H]- Ketanserin binding to 5-hydroxytryptamine 2A re... 11784139
5-hydroxytryptamine receptor 6 Ki = 0.4 nM 9.4 Binding affinity towards human 5-hydroxytryptamine 6 receptor was evaluated usin... 12825922
5-hydroxytryptamine receptor 7 Ki = 0.5495 nM 9.26 Displacement of [3H]-LSD from recombinant human 5HT7 receptor expressed in CHOK1... 32105980
5-hydroxytryptamine receptor 7 Ki = 0.5623 nM 9.25 Displacement of [3H]-LSD from human 5-HT7 receptor transfected in CHO-K1 cells m... 34436892
5-hydroxytryptamine receptor 7 EC50 = 0.6 nM 9.22 Displacement of [3H]lysergic acid from human recombinant 5HT7 receptor expressed... 16562853
5-hydroxytryptamine receptor 7 IC50 = 0.82 nM 9.09 Antagonist activity at 5HT7R receptor (unknown origin) assessed as forskolin-med... 31627993
5-hydroxytryptamine receptor 6 Ki = 0.9 nM 9.05 Displacement of [3H]LSD from recombinant human 5-HT6 receptor expressed in CHO c... 29730027
5-hydroxytryptamine receptor 7 Ki = 0.9 nM 9.05 Displacement of [3H]LSD from human recombinant 5-HT7 receptor expressed in CHO-K... 24805037
5-hydroxytryptamine receptor 6 Ki = 0.9333 nM 9.03 Displacement of [3H]-LSD from human 5-HT6 receptor transfected in CHO-K1 cells m... 34436892
5-hydroxytryptamine receptor 6 Ki = 0.9772 nM 9.01 Displacement of [3H]-LSD from recombinant human 5HT6 receptor expressed in CHOK1... 32105980
5-hydroxytryptamine receptor 5A Ki = 1.0 nM 9.0 Binding affinity towards human 5-hydroxytryptamine 5A receptor was evaluated usi... 12825922
5-hydroxytryptamine receptor 6 Ki = 1.0 nM 9.0 Displacement of [3H]-LSD from human 5-HT6 receptor extracted from CHO-K1 cell me... 38901106
5-hydroxytryptamine receptor 6 Ki = 1.0 nM 9.0 Displacement of [3H]-LSD from human 5-HT6 receptor expressed in CHO-K1 cell memb... 28763213
5-hydroxytryptamine receptor 7 Ki = 1.0 nM 9.0 Displacement of [3H]-LSD from human 5-HT7 receptor expressed in CHO-K1 cell memb... 28763213
5-hydroxytryptamine receptor 5A Ki = 1.0 nM 9.0 Binding affinity towards human 5-hydroxytryptamine 5A receptor 12825922
5-hydroxytryptamine receptor 6 Ki = 1.3 nM 8.89 Displacement of [3H]-LSD from human 5-HT6 receptor expressed in HEK cell membran... 37003157

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 73
- 10.5281/zenodo.13943903 ADMET 73
18033297 10.1038/nature05991 Caenorhabditis elegans 16
26996373 10.1016/j.bmcl.2016.03.036 5-hydroxytryptamine receptor 6 5
35421658 10.1016/j.ejmech.2022.114306 Protein patched homolog 1 4
38901106 10.1016/j.ejmech.2024.116601 5-hydroxytryptamine receptor 6 4
35421658 10.1016/j.ejmech.2022.114306 Unchecked 3
21784633 10.1016/j.bmcl.2011.06.120 Unchecked 3
25052428 10.1016/j.bmcl.2014.06.082 G protein-coupled receptor 3
25557493 10.1016/j.ejmech.2014.12.045 5-hydroxytryptamine receptor 6 3
12825922 10.1021/jm030030n 5-hydroxytryptamine receptor 5A 3
25052428 10.1016/j.bmcl.2014.06.082 G-protein coupled receptor homolog US28 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
24805037 10.1021/jm401895u 5-hydroxytryptamine receptor 7 2
25965777 10.1016/j.ejmech.2015.04.046 5-hydroxytryptamine receptor 7 2
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
18033297 10.1038/nature05991 5-hydroxytryptamine receptor 3A 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32877805 10.1016/j.ejmech.2020.112709 5-hydroxytryptamine receptor 7 2
25965777 10.1016/j.ejmech.2015.04.046 5-hydroxytryptamine receptor 6 2

Data from ChEMBL 36 via Core Engine