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Compound Detail

CHEMBL91157

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COc1cc2c(cc1OC)C1=NO[C@@H](CN3CCN(C/C(C)=C/c4ccccc4)CC3)[C@@H]1CO2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL91157
Phase Preclinical
Structure Type MOL
InChI Key JWYUBODPEUBFLH-FSTMKDAKSA-N
11
Targets
24
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

463.6
MW (Da)
3.54
ALogP
7
HBA
0
HBD
55.8
PSA (Ų)
0.63
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H33N3O4
MW 463.58
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness -0.12

Activity Summary

Ki 24 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 10.0 9.65 0.1 5
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 9.52 9.008 0.3 5
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.64 8.5167 2.3 3
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 8.55 8.41 2.8 2
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 8.52 8.2867 3.0 3
Histamine H1 receptor
CHEMBL231
 Ki 6.95 6.95 113.0 1
Norepinephrine transporter
CHEMBL304
 Ki 6.75 6.75 177.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 6.64 6.64 230.0 1
Adrenergic receptor alpha-1
CHEMBL2094251
 Ki 6.42 6.42 380.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 6.36 6.36 433.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 6.32 6.32 475.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-2C adrenergic receptor Ki = 0.1 nM 10.0 Inhibition of [3H]- rauwolscine binding to alpha-2C adrenergic receptor 15771448
Alpha-2C adrenergic receptor Ki = 0.1 nM 10.0 In vitro binding affinity towards human adrenergic alpha-2C adrenergic receptor ... 12873501
Alpha-2C adrenergic receptor Ki = 0.2 nM 9.7 In vitro binding affinity to human alpha-2C adrenergic receptor 15125959
Alpha-2C adrenergic receptor Ki = 0.2 nM 9.7 Binding affinity for alpha-2C-adrenergic receptor 15771448
Alpha-2A adrenergic receptor Ki = 0.3 nM 9.52 In vitro binding affinity towards human alpha-2A adrenergic receptor using [3H]r... 12873501
Alpha-2A adrenergic receptor Ki = 0.3 nM 9.52 Inhibition of [3H]- rauwolscine binding to human alpha-2A adrenergic receptor 15771448
Alpha-2A adrenergic receptor Ki = 0.8 nM 9.1 In vitro binding affinity to the human alpha-2A adrenergic receptor 15125959
Alpha-2A adrenergic receptor Ki = 0.8 nM 9.1 Binding affinity for alpha-2A-adrenergic receptor 15771448
Alpha-2C adrenergic receptor Ki = 1.4 nM 8.85 In vitro binding affinity towards human adrenergic alpha-2C adrenergic receptor ... 12873501
Sodium-dependent serotonin transporter Ki = 2.3 nM 8.64 In vitro binding affinity towards human serotonin transporter 15125959
Sodium-dependent serotonin transporter Ki = 2.3 nM 8.64 Binding affinity for serotonin transporter 15771448
Sodium-dependent serotonin transporter Ki = 2.8 nM 8.55 In vitro binding affinity towards rat serotonin transporter 12873501
Alpha-2B adrenergic receptor Ki = 3.0 nM 8.52 In vitro binding affinity towards human alpha-2B adrenergic receptor using [3H]r... 12873501
Alpha-2B adrenergic receptor Ki = 3.0 nM 8.52 Inhibition of [3H]- rauwolscine binding to alpha-2B adrenergic receptor 15771448
Sodium-dependent serotonin transporter Ki = 5.4 nM 8.27 In vitro binding affinity towards rat serotonin transporter 12873501
Sodium-dependent serotonin transporter Ki = 5.4 nM 8.27 Inhibition of [3H]- paroxetine binding to 5-HTT receptor, serotonin transporter 15771448
Alpha-2B adrenergic receptor Ki = 15.0 nM 7.82 In vitro binding affinity towards human alpha-2B adrenergic receptor using [3H]r... 12873501
Alpha-2A adrenergic receptor Ki = 16.0 nM 7.8 In vitro binding affinity towards human alpha-2A adrenergic receptor using [3H]r... 12873501
Histamine H1 receptor Ki = 113.0 nM 6.95 Inhibition of [3H]pyrilamine binding to Histamine H1 receptor 15771448
Norepinephrine transporter Ki = 177.0 nM 6.75 Inhibition of [3H]-nisoxetine binding to Norepinephrine transporter from rat cor... 15771448

Literature References

PubMed DOI Target Context # Activities
15771448 10.1021/jm049619s Rattus norvegicus 5
12873501 10.1016/s0960-894x(03)00525-0 Sodium-dependent serotonin transporter 4
15771448 10.1021/jm049619s Alpha-2C adrenergic receptor 2
15125959 10.1016/j.bmcl.2004.03.031 Sodium-dependent serotonin transporter 2
15771448 10.1021/jm049619s Sodium-dependent serotonin transporter 2
12873501 10.1016/s0960-894x(03)00525-0 Alpha-2A adrenergic receptor 2
12873501 10.1016/s0960-894x(03)00525-0 Alpha-2B adrenergic receptor 2
12873501 10.1016/s0960-894x(03)00525-0 Alpha-2C adrenergic receptor 2
12873501 10.1016/s0960-894x(03)00525-0 Adrenergic receptor alpha-2 2
15771448 10.1021/jm049619s Alpha-2A adrenergic receptor 2
15771448 10.1021/jm049619s 5-hydroxytryptamine receptor 7 1
15771448 10.1021/jm049619s 5-hydroxytryptamine receptor 1A 1
15771448 10.1021/jm049619s Norepinephrine transporter 1
15771448 10.1021/jm049619s Sodium-dependent dopamine transporter 1
15771448 10.1021/jm049619s D(4) dopamine receptor 1
15771448 10.1021/jm049619s D(3) dopamine receptor 1
15771448 10.1021/jm049619s D(2) dopamine receptor 1
15771448 10.1021/jm049619s Histamine H1 receptor 1
15125959 10.1016/j.bmcl.2004.03.031 Alpha-2A adrenergic receptor 1
15125959 10.1016/j.bmcl.2004.03.031 Adrenergic receptor alpha-2 1

Data from ChEMBL 36 via Core Engine