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Compound Detail

CHEMBL560

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CC(C)=CCN1CC[C@@]2(C)c3cc(O)ccc3C[C@@H]1[C@@H]2C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL560
Phase Preclinical
Structure Type MOL
InChI Key VOKSWYLNZZRQPF-GDIGMMSISA-N
10
Targets
26
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

285.4
MW (Da)
3.88
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.83
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H27NO
MW 285.43
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 1.75

Activity Summary

Ki 23 meas. best 8.66
IC50 3 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 8.66 8.59 2.2 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 8.44 8.44 3.6 1
Mu-type opioid receptor
CHEMBL233
 Ki 8.41 8.285 3.9 2
Mu-type opioid receptor
CHEMBL4354
 Ki 8.34 8.34 4.6 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 IC50 8.05 7.4533 8.9 3
Mu-type opioid receptor
CHEMBL270
 Ki 7.89 7.89 13.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 Ki 7.82 7.625 15.0 4
Unchecked
CHEMBL612545
 Ki 7.64 7.0125 23.1 4
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 7.44 7.128 36.5 5
Delta-type opioid receptor
CHEMBL236
 Ki 7.31 7.03 49.0 2
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 7.08 7.08 83.4 1

Pharmacokinetic Data

Parameter Value Units Species
F 49.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 2.2 nM 8.66 Displacement of [125I]OXY from human kappa opioid receptor expressed in CHO cell... 20055417
Kappa-type opioid receptor Ki = 3.0 nM 8.52 Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cel... 19027293
Kappa-type opioid receptor Ki = 3.6 nM 8.44 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum h... 21641798
Mu-type opioid receptor Ki = 3.9 nM 8.41 Displacement of [125I]OXY from human mu opioid receptor expressed in CHO cells 20055417
Mu-type opioid receptor Ki = 4.6 nM 8.34 Displacement of [3H]DAMGO from mu opioid receptor in guinea pig forebrain homoge... 21641798
Mu-type opioid receptor Ki = 6.9 nM 8.16 Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells 19027293
Sigma non-opioid intracellular receptor 1 IC50 = 8.9 nM 8.05 Compound was evaluated for the binding affinity towards Sigma receptor type 1 us... 7783132
Mu-type opioid receptor Ki = 13.0 nM 7.89 Binding affinity against opioid receptor mu using [3H]-DAMGO as radioligand. 1322987
Sigma non-opioid intracellular receptor 1 Ki = 15.0 nM 7.82 Displacement of [3H]-pentazocine from sigma 1 opioid receptor in rat liver homog... 24900272
Sigma non-opioid intracellular receptor 1 Ki = 16.0 nM 7.8 Displacement of [3H](+)-pentazocine from sigma1 receptor in rat brain homogenate 20055417
Unchecked Ki = 23.1 nM 7.64 Displacement of [3H]NTI from delta opioid receptor in guinea pig forebrain homog... 21641798
Sigma non-opioid intracellular receptor 1 IC50 = 29.0 nM 7.54 Binding affinity towards Sigma receptor type 2 in whole rat brain homogenates ex... 7783132
Sigma non-opioid intracellular receptor 1 Ki = 36.5 nM 7.44 Binding affinity at Sigma receptor type 2 on rat liver membranes receptor by [3H... 7636860
Sigma non-opioid intracellular receptor 1 Ki = 36.5 nM 7.44 Affinity against Sigma opioid receptor type 2 using [3H]- DTG in rat liver membr... 10579824
Sigma non-opioid intracellular receptor 1 Ki = 36.5 nM 7.44 Binding affinity was measured on Sigma receptor type 2 using [3H]- DTG as radiol... 7636861
Delta-type opioid receptor Ki = 49.0 nM 7.31 Displacement of [125I]OXY from human delta opioid receptor expressed in CHO cell... 20055417
Unchecked Ki = 56.0 nM 7.25 Displacement of [3H]di-O-tolyguanidine from sigma2 receptor in rat brain homogen... 20055417
Sigma non-opioid intracellular receptor 1 Ki = 83.1 nM 7.08 Binding affinity measured on Sigma receptor type 1 from guinea pig brain membran... 7636860
Sigma non-opioid intracellular receptor 1 Ki = 83.1 nM 7.08 Binding affinity was measured on Sigma receptor type 1 using [3H]- pentazocine a... 7636861
Sigma non-opioid intracellular receptor 1 Ki = 83.1 nM 7.08 Affinity against Sigma opioid receptor type 1 using [3H](+)-pentazocine in guine... 10579824

Literature References

PubMed DOI Target Context # Activities
10649973 10.1021/jm980333v Mus musculus 4
20055417 10.1021/jm901503e Unchecked 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
7636860 10.1021/jm00015a022 Sigma non-opioid intracellular receptor 1 3
22877623 10.1016/j.ejmech.2012.07.002 Mus musculus 3
7783132 10.1021/jm00011a020 Sigma non-opioid intracellular receptor 1 3
7636861 10.1021/jm00015a023 Sigma non-opioid intracellular receptor 1 3
- 10.1007/s00044-011-9569-5 Mus musculus 3
1322987 10.1021/jm00093a014 Unchecked 3
19027293 10.1016/j.bmcl.2008.10.134 Unchecked 2
21641798 10.1016/j.bmcl.2011.04.147 Unchecked 2
- 10.1007/s00044-010-9489-9 Mus musculus 2
10579824 10.1021/jm990169r Sigma non-opioid intracellular receptor 1 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2
8164264 10.1021/jm00034a020 Sigma non-opioid intracellular receptor 1 1
1322987 10.1021/jm00093a014 Mu-type opioid receptor 1
18774292 10.1016/j.bmcl.2008.08.065 Sodium-dependent dopamine transporter 1
2999399 10.1021/jm00149a020 Mus musculus 1
6166748 10.1021/jm00138a015 Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine