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Compound Detail

CHEMBL268258

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COc1cccc2c1CCC[C@H]2CN(C)CCc1ccc2ccoc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL268258
Phase Preclinical
Structure Type MOL
InChI Key MHPMXTGKTXJIDI-IBGZPJMESA-N
17
Targets
27
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

349.5
MW (Da)
5.04
ALogP
3
HBA
0
HBD
25.6
PSA (Ų)
0.62
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H27NO2
MW 349.47
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness 0.07

Activity Summary

Ki 22 meas. best 8.7
IC50 5 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adrenergic receptor alpha-2
CHEMBL2093864
 Ki 8.7 8.7 2.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 8.7 8.7 2.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 8.68 8.68 2.1 2
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 8.62 8.61 2.4 2
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.42 8.41 3.8 2
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 8.4 8.4 4.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 7.96 7.96 11.0 2
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.89 7.89 13.0 1
Rattus norvegicus
CHEMBL376
 IC50 7.88 6.49 13.1 3
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 7.88 7.88 13.1 1
D(2) dopamine receptor
CHEMBL339
 Ki 7.28 7.28 52.0 2
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 6.96 6.96 110.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 6.84 6.84 144.0 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 6.84 6.84 144.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 6.63 6.63 234.0 1
D(1A) dopamine receptor
CHEMBL265
 Ki 6.13 6.13 744.0 1
Beta-1 adrenergic receptor
CHEMBL3252
 Ki 6.08 6.08 836.0 1
Beta-2 adrenergic receptor
CHEMBL2289
 Ki 5.76 5.76 1740.0 1
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
 Ki 5.53 5.53 2970.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adrenergic receptor alpha-2 Ki = 2.01 nM 8.7 Evaluated for affinity at Alpha-2 adrenergic receptor of rat cortex using [3H]ra... -
Adrenergic receptor alpha-2 Ki = 2.01 nM 8.7 Ability to displace [3H]rauwolscine from Alpha-2 adrenergic receptor in rat cort... 9089327
5-hydroxytryptamine receptor 1A Ki = 2.0 nM 8.7 Inhibition constant against 5-hydroxytryptamine 1A receptor 16220969
Alpha-2C adrenergic receptor Ki = 2.1 nM 8.68 In vitro binding affinity towards human adrenergic alpha-2C adrenergic receptor ... 12873501
Alpha-2C adrenergic receptor Ki = 2.1 nM 8.68 Inhibition of [3H]- rauwolscine binding to alpha-2C adrenergic receptor 15771448
Alpha-2A adrenergic receptor Ki = 2.4 nM 8.62 In vitro binding affinity towards human alpha-2A adrenergic receptor using [3H]r... 12873501
Alpha-2A adrenergic receptor Ki = 2.5 nM 8.6 Inhibition of [3H]- rauwolscine binding to human alpha-2A adrenergic receptor 15771448
Sodium-dependent serotonin transporter Ki = 3.77 nM 8.42 Evaluated for affinity at 5-HT uptake site using [3H]paroxetine as radioligand i... -
Sodium-dependent serotonin transporter Ki = 4.0 nM 8.4 Inhibition of [3H]- paroxetine binding to 5-HTT receptor, serotonin transporter 15771448
Sodium-dependent serotonin transporter Ki = 4.0 nM 8.4 In vitro binding affinity towards rat serotonin transporter 12873501
Alpha-2B adrenergic receptor Ki = 11.0 nM 7.96 Inhibition of [3H]- rauwolscine binding to alpha-2B adrenergic receptor 15771448
Alpha-2B adrenergic receptor Ki = 11.0 nM 7.96 In vitro binding affinity towards human alpha-2B adrenergic receptor using [3H]r... 12873501
Sodium-dependent serotonin transporter IC50 = 13.0 nM 7.89 Inhibitory concentration against serotonin transporter 16220969
Rattus norvegicus IC50 = 13.1 nM 7.88 Evaluated for inhibition of 5-Hydroxytryptamine, biogenic amine reuptake in syna... -
Sodium-dependent serotonin transporter IC50 = 13.1 nM 7.88 Inhibition of uptake of [3H]5-HT in synaptosomes from rat cortex 9089327
D(2) dopamine receptor Ki = 52.0 nM 7.28 Compound was evaluated for its binding affinity to Dopamine receptor D2 in rat b... -
D(2) dopamine receptor Ki = 52.0 nM 7.28 Inhibition constant against Dopamine receptor D2 in olfactory bulbectomized rat 16220969
Adrenergic receptor alpha-1 Ki = 110.0 nM 6.96 Evaluated for affinity at Alpha-1 adrenergic receptor of rat brain using [3H]pra... -
Serotonin 2 (5-HT2) receptor Ki = 144.0 nM 6.84 Compound was evaluated for its binding affinity to 5-hydroxytryptamine 2 recepto... -
5-hydroxytryptamine receptor 2A Ki = 144.0 nM 6.84 Inhibition constant against 5-Hydroxytryptamine 2 receptor in olfactory bulbecto... 16220969

Literature References

PubMed DOI Target Context # Activities
- 10.1016/0960-894X(95)00398-D Rattus norvegicus 5
15771448 10.1021/jm049619s Rattus norvegicus 4
15771448 10.1021/jm049619s Sodium-dependent serotonin transporter 2
12873501 10.1016/s0960-894x(03)00525-0 Sodium-dependent serotonin transporter 2
12873501 10.1016/s0960-894x(03)00525-0 Alpha-2A adrenergic receptor 1
15771448 10.1021/jm049619s Histamine H1 receptor 1
15771448 10.1021/jm049619s Alpha-2A adrenergic receptor 1
16220969 10.1021/jm058225d 5-hydroxytryptamine receptor 2A 1
9089327 10.1021/jm960723m Adrenergic receptor alpha-2 1
12873501 10.1016/s0960-894x(03)00525-0 Adrenergic receptor alpha-2 1
12873501 10.1016/s0960-894x(03)00525-0 Alpha-2C adrenergic receptor 1
12873501 10.1016/s0960-894x(03)00525-0 Alpha-2B adrenergic receptor 1
- 10.1016/0960-894X(95)00398-D Adrenergic receptor alpha-1 1
- 10.1016/0960-894X(95)00398-D Serotonin 2 (5-HT2) receptor 1
- 10.1016/0960-894X(95)00398-D Serotonin 1 (5-HT1) receptor 1
- 10.1016/0960-894X(95)00398-D D(2) dopamine receptor 1
- 10.1016/0960-894X(95)00398-D D(1A) dopamine receptor 1
- 10.1016/0960-894X(95)00398-D Beta-2 adrenergic receptor 1
- 10.1016/0960-894X(95)00398-D Beta-1 adrenergic receptor 1
- 10.1016/0960-894X(95)00398-D Sodium-dependent serotonin transporter 1

Data from ChEMBL 36 via Core Engine