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Compound Detail

CHEMBL133455

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C[C@H](N)Cc1c[nH]c2ccc3c(c12)CCCO3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL133455
Phase Preclinical
Structure Type MOL
InChI Key VVHJUSGIUWQPIT-VIFPVBQESA-N
9
Targets
11
Activities
3
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

230.3
MW (Da)
2.38
ALogP
2
HBA
2
HBD
51.0
PSA (Ų)
0.83
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H18N2O
MW 230.31
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness 0.10

Activity Summary

Ki 7 meas. best 9.7
IC50 3 meas. best 9.3
EC50 1 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 9.7 9.7 0.2 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 IC50 9.3 9.3 0.5 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 8.7 8.7 2.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 8.47 8.47 3.4 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 8.28 8.28 5.3 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 EC50 7.1 7.1 80.1 1
5-hydroxytryptamine receptor 4
CHEMBL1875
 Ki 5.77 5.77 1700.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 5.66 5.66 2200.0 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 5.48 5.48 3300.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 IC50 4.85 4.85 14000.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 4.72 4.72 19000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.2 nM 9.7 In vitro inhibitory constant against [125I]DOI binding to 5-hydroxytryptamine 2A... 12954071
5-hydroxytryptamine receptor 2A IC50 = 0.5 nM 9.3 In vitro inhibition of [125I]DOI binding to 5-hydroxytryptamine 2A receptor in r... 12954071
5-hydroxytryptamine receptor 2A Ki = 2.0 nM 8.7 Inhibitory constant against cloned human 5-hydroxytryptamine 2A receptor using w... 12954071
5-hydroxytryptamine receptor 2C Ki = 3.4 nM 8.47 Inhibitory constant against cloned human 5-hydroxytryptamine 2C receptor using w... 12954071
5-hydroxytryptamine receptor 2B Ki = 5.3 nM 8.28 Inhibitory constant against cloned human 5-hydroxytryptamine 2B receptor using w... 12954071
5-hydroxytryptamine receptor 2A EC50 = 80.1 nM 7.1 In vitro relative agonist activity against 5-hydroxytryptamine 2A using PI assay... 12954071
5-hydroxytryptamine receptor 4 Ki = 1700.0 nM 5.77 Inhibitory constant against 5-hydroxytryptamine 4 receptor using [3H]GR-113808 r... 12954071
5-hydroxytryptamine receptor 6 Ki = 2200.0 nM 5.66 Inhibitory constant against human 5-hydroxytryptamine 6 receptor using [3H]LSD r... 12954071
5-hydroxytryptamine receptor 1B Ki = 3300.0 nM 5.48 Inhibitory constant against 5-hydroxytryptamine 1B receptor using with [125I]- c... 12954071
Alpha-2C adrenergic receptor IC50 = 14000.0 nM 4.85 Inhibitory concentration required against Alpha-2A adrenergic receptor using [3H... 12954071
Alpha-2A adrenergic receptor IC50 = 19000.0 nM 4.72 Inhibitory concentration required against Alpha-2A adrenergic receptor using [3H... 12954071

Literature References

PubMed DOI Target Context # Activities
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 2A 7
12954071 10.1021/jm030205t Monkey 3
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 1A 2
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 7 1
12954071 10.1021/jm030205t Sodium-dependent serotonin transporter 1
12954071 10.1021/jm030205t Sodium-dependent noradrenaline transporter 1
12954071 10.1021/jm030205t Alpha-2C adrenergic receptor 1
12954071 10.1021/jm030205t Alpha-2B adrenergic receptor 1
12954071 10.1021/jm030205t Alpha-2A adrenergic receptor 1
12954071 10.1021/jm030205t Alpha-1B adrenergic receptor 1
12954071 10.1021/jm030205t Alpha-1A adrenergic receptor 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 2B 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 6 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 5A 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 4 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 3A 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 1D 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 1B 1
12954071 10.1021/jm030205t 5-hydroxytryptamine receptor 2C 1

Data from ChEMBL 36 via Core Engine