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Compound Detail

CHEMBL74355

VOLINANSERIN
🧪 Phase III
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🧪 Phase III
COc1cccc([C@H](O)C2CCN(CCc3ccc(F)cc3)CC2)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL74355
Name VOLINANSERIN
Phase Phase III
Structure Type MOL
InChI Key HXTGXYRHXAGCFP-OAQYLSRUSA-N

Known Names

M-100907 M100907 MDL-100.907 Mdl-100907 MDL100.907 Volinanserin Volinanserina Volinanserine
15
Targets
44
Activities
3
Assay Types
6
PK Parameters
20
Publications
8
Known Names
2
Indications
1
Mechanisms

Molecular Properties

373.5
MW (Da)
3.83
ALogP
4
HBA
1
HBD
41.9
PSA (Ų)
0.80
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -anserin

Extended Properties

Molecular Formula C22H28FNO3
MW 373.47
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.73

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin 2a (5-HT2a) receptor antagonist ANTAGONIST 5-hydroxytryptamine receptor 2A ✓ ✓

Indications

Sleep Wake Disorders Depressive Disorder

Activity Summary

Ki 41 meas. best 10.0
IC50 2 meas. best 8.32
Kd 1 meas. best 9.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 10.0 9.2957 0.1 7
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 10.0 9.4056 0.1 9
5-hydroxytryptamine receptor 2A
CHEMBL224
 Kd 9.85 9.85 0.1 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 IC50 8.32 8.32 4.8 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 7.89 7.3467 13.0 6
Kappa-type opioid receptor
CHEMBL237
 Ki 6.99 6.99 102.7 1
Unchecked
CHEMBL612545
 Ki 6.89 6.89 128.0 1
Histamine H1 receptor
CHEMBL231
 Ki 6.88 6.44 132.5 2
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 6.69 6.69 205.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 6.38 6.38 420.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 6.07 6.07 859.3 1
Potassium voltage-gated channel subfamily KQT member 1
CHEMBL1866
 Ki 5.97 5.97 1060.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 5.96 5.96 1100.0 4
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 5.9 5.9 1258.9 1
D(2) dopamine receptor
CHEMBL217
 Ki 5.89 5.83 1300.0 4
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 5.89 5.89 1288.5 1
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 5.42 5.42 3807.6 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8.0 ng.hr.mL-1 -
Cmax 5.355 nM -
F 3.0 % Eutheria
MRT 1.0 hr -
T1/2 6.6 hr Homo sapiens
Vd 4.6 L.kg-1 -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.1 nM 10.0 Binding affinity for displacement of [3H]ketanserin to rat 5-hydroxytryptamine 2... 11784153
5-hydroxytryptamine receptor 2A Ki = 0.1 nM 10.0 Binding affinity against rat 5-hydroxytryptamine 2A receptor 15993598
5-hydroxytryptamine receptor 2A Ki = 0.1 nM 10.0 Antagonist activity at human 5HT2A receptor expressed in HEK cells assessed as i... 20942472
5-hydroxytryptamine receptor 2A Kd = 0.14 nM 9.85 Binding affinity to human brain homogenate 5-HT2A assessed as dissociation const... 35939391
5-hydroxytryptamine receptor 2A Ki = 0.3 nM 9.52 Ability to displace [3H]ketanserin from CHO cells expressing human 5-hydroxytryp... 11133070
5-hydroxytryptamine receptor 2A Ki = 0.31 nM 9.51 Binding affinity for displacement of [3H]ketanserin to human 5-hydroxytryptamine... 11784153
5-hydroxytryptamine receptor 2A Ki = 0.31 nM 9.51 Binding affinity against human 5-hydroxytryptamine 2A receptor 15993598
5-hydroxytryptamine receptor 2A Ki = 0.31 nM 9.51 Displacement of [3H]- ketanserin from human 5HT2A receptor expressed CHO cells 20493697
5-hydroxytryptamine receptor 2A Ki = 0.36 nM 9.44 Binding affinity against 5-hydroxytryptamine 2A receptor in humans 12014970
5-hydroxytryptamine receptor 2A Ki = 0.36 nM 9.44 Displacement of [3H]MDL100907 from rat cortical membrane 5HT2A receptor 19329329
5-hydroxytryptamine receptor 2A Ki = 0.38 nM 9.42 Displacement of [3H]MDL from rat 5HT2A receptor expressed in GF62 cells by liqui... 19329329
5-hydroxytryptamine receptor 2A Ki = 0.57 nM 9.24 Binding affinity to 5HT2A receptor 18187324
5-hydroxytryptamine receptor 2A Ki = 0.7877 nM 9.1 PDSP Secondary Binding target: HTR2A - Compounds are tested at 10 uM concentrati... -
5-hydroxytryptamine receptor 2A Ki = 1.4 nM 8.85 Binding affinity towards rat 5-hydroxytryptamine 2A receptor 11170639
5-hydroxytryptamine receptor 2A Ki = 1.5 nM 8.82 Binding affinity for human 5-hydroxytryptamine 2A receptor 11170639
5-hydroxytryptamine receptor 2A Ki = 2.1 nM 8.68 Displacement of [3H]MDL from rat 5HT2A receptor expressed in GF62 cells 18187324
5-hydroxytryptamine receptor 2A Ki = 2.1 nM 8.68 Displacement of [3H]MDL from rat 5HT2A receptor expressed in GF62 cells by liqui... 19329329
5-hydroxytryptamine receptor 2A IC50 = 4.786 nM 8.32 Antagonist activity at human recombinant 5-HT2A receptor expressed in CHOK1 cell... 29555153
5-hydroxytryptamine receptor 2A IC50 = 4.8 nM 8.32 Antagonist activity at human recombinant 5-HT2A receptor expressed in CHOK1 cell... 29555153
5-hydroxytryptamine receptor 2C Ki = 13.0 nM 7.89 Binding affinity for displacement of [3H]mesulergine to human 5-hydroxytryptamin... 11784153

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 Fibroblast 8
- 10.6019/CHEMBL4689842 U2OS 7
11784153 10.1021/jm011030v ADMET 6
29555153 10.1016/j.bmcl.2018.02.058 5-hydroxytryptamine receptor 2A 4
33887904 10.1021/acs.jmedchem.1c00484 Unchecked 4
19329329 10.1016/j.bmc.2009.03.021 5-hydroxytryptamine receptor 2A 3
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
19329329 10.1016/j.bmc.2009.03.021 No relevant target 2
18187324 10.1016/j.bmcl.2007.12.054 5-hydroxytryptamine receptor 2A 2
- 10.6019/CHEMBL3301361 ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 2
15993598 10.1016/j.bmcl.2005.05.104 5-hydroxytryptamine receptor 2A 2
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
11170639 10.1021/jm0002432 5-hydroxytryptamine receptor 2A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 2
11784153 10.1021/jm011030v 5-hydroxytryptamine receptor 2A 2

Data from ChEMBL 36 via Core Engine