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Compound Detail

CHEMBL326684

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CO[C@@]12CCC(=O)[C@]3(C)Oc4c(O)ccc5c4[C@@]31CCN(C)[C@@H]2C5
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL326684
Phase Preclinical
Structure Type MOL
InChI Key DENICFHULARDRG-WEZQJLTASA-N
8
Targets
15
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

329.4
MW (Da)
1.79
ALogP
5
HBA
1
HBD
59.0
PSA (Ų)
0.85
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H23NO4
MW 329.40
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 2.07

Activity Summary

Ki 12 meas. best 11.0
IC50 2 meas. best 8.21
EC50 1 meas. best 8.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 11.0 10.3 0.0 2
Mu-type opioid receptor
CHEMBL270
 Ki 10.64 10.23 0.0 2
Mu-type opioid receptor
CHEMBL233
 EC50 8.48 8.48 3.3 1
Mu-type opioid receptor
CHEMBL4354
 IC50 8.21 8.21 6.1 1
Delta-type opioid receptor
CHEMBL236
 Ki 7.88 7.79 13.3 2
Delta-type opioid receptor
CHEMBL269
 Ki 7.88 7.635 13.3 2
Kappa-type opioid receptor
CHEMBL237
 Ki 7.82 7.3133 15.1 3
Delta-type opioid receptor
CHEMBL3222
 IC50 7.61 7.61 24.4 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 7.6 7.6 25.2 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.01 nM 11.0 Binding affinity at mu opioid receptor (unknown origin) 26656913
Mu-type opioid receptor Ki = 0.023 nM 10.64 In vitro binding affinity at opioid receptor mu 1 was determined in C6 rat gliom... 12699394
Mu-type opioid receptor Ki = 0.15 nM 9.82 Inhibition of [3H]DAMGO binding to opioid receptor mu from rat brain membranes 15857143
Mu-type opioid receptor Ki = 0.25 nM 9.6 Displacement of [3H]-DAMGO from recombinant human MOR expressed in CHO cell memb... 29053268
Mu-type opioid receptor EC50 = 3.28 nM 8.48 Agonist activity at recombinant human MOR expressed in CHO cell membranes after ... 29053268
Mu-type opioid receptor IC50 = 6.1 nM 8.21 In vitro agonistic activity against opioid receptor mu of guinea pig ileum 15857143
Delta-type opioid receptor Ki = 13.3 nM 7.88 Inhibition of [3H][Ile5,6]deltorphin II binding to opioid receptor delta from ra... 15857143
Delta-type opioid receptor Ki = 13.3 nM 7.88 Binding affinity at delta opioid receptor (unknown origin) 26656913
Kappa-type opioid receptor Ki = 15.1 nM 7.82 Displacement of [3H]-HS665 from recombinant human KOR expressed in CHO cell memb... 29053268
Delta-type opioid receptor Ki = 19.8 nM 7.7 Displacement of [3H]-diprenorphine from recombinant human DOR expressed in CHO c... 29053268
Delta-type opioid receptor IC50 = 24.4 nM 7.61 In vitro agonistic activity against opioid receptor delta of mouse vas deferens 15857143
Kappa-type opioid receptor Ki = 25.2 nM 7.6 Inhibition of [3H]U-69593 binding to opioid receptor kappa from guinea pig brain... 15857143
Kappa-type opioid receptor Ki = 25.2 nM 7.6 Binding affinity to kappa opioid receptor (unknown origin) 26656913
Delta-type opioid receptor Ki = 40.9 nM 7.39 In vitro binding affinity at opioid receptor delta 1 was determined in C6 rat gl... 12699394
Kappa-type opioid receptor Ki = 304.0 nM 6.52 In vitro binding affinity at opioid receptor kappa 1 was determined in human CHO... 12699394

Literature References

PubMed DOI Target Context # Activities
29053268 10.1021/acs.jmedchem.7b01363 Mu-type opioid receptor 5
29053268 10.1021/acs.jmedchem.7b01363 Mus musculus 4
12699394 10.1021/jm021118o Unchecked 3
15163203 10.1021/jm031126k Mus musculus 3
29053268 10.1021/acs.jmedchem.7b01363 Unchecked 2
15857143 10.1021/jm040894o Mu-type opioid receptor 2
15857143 10.1021/jm040894o Mus musculus 2
15857143 10.1021/jm040894o Delta-type opioid receptor 2
15857143 10.1021/jm040894o Unchecked 2
15857143 10.1021/jm040894o Kappa-type opioid receptor 1
29053268 10.1021/acs.jmedchem.7b01363 Kappa-type opioid receptor 1
29053268 10.1021/acs.jmedchem.7b01363 Delta-type opioid receptor 1
26656913 10.1016/j.ejmech.2015.11.028 Kappa-type opioid receptor 1
26656913 10.1016/j.ejmech.2015.11.028 Delta-type opioid receptor 1
26656913 10.1016/j.ejmech.2015.11.028 Mu-type opioid receptor 1
15857143 10.1021/jm040894o Opioid receptors; mu & delta 1
12699394 10.1021/jm021118o Opioid receptor 1
12699394 10.1021/jm021118o Opioid receptors; mu and delta 1
12699394 10.1021/jm021118o Kappa-type opioid receptor 1
12699394 10.1021/jm021118o Delta-type opioid receptor 1

Data from ChEMBL 36 via Core Engine