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Compound Detail

CHEMBL473136

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COC(=O)/C=C/C(=O)N[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL473136
Phase Preclinical
Structure Type MOL
InChI Key PQKHESYTSKMWFP-WZJCLRDWSA-N
11
Targets
20
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

454.5
MW (Da)
1.17
ALogP
7
HBA
3
HBD
108.3
PSA (Ų)
0.45
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H30N2O6
MW 454.52
Aromatic Rings 1
Heavy Atoms 33
NP-Likeness 1.31

Activity Summary

Ki 13 meas. best 9.4
IC50 7 meas. best 8.99

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL4354
 Ki 9.4 9.4 0.4 2
Mu-type opioid receptor
CHEMBL233
 Ki 9.39 9.39 0.4 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.05 8.4267 0.9 3
Kappa-type opioid receptor
CHEMBL237
 Ki 9.03 9.03 0.9 2
Opioid receptor
CHEMBL2094129
 IC50 8.99 8.99 1.0 1
Mu-type opioid receptor
CHEMBL4354
 IC50 8.66 8.49 2.2 2
Cavia porcellus
CHEMBL369
 IC50 8.32 8.32 4.8 1
Unchecked
CHEMBL612545
 Ki 8.11 8.11 7.7 1
Delta-type opioid receptor
CHEMBL236
 Ki 7.65 7.59 22.4 3
Mus musculus
CHEMBL375
 IC50 7.46 7.46 35.0 1
Opioid receptor
CHEMBL2095192
 IC50 7.09 7.09 82.0 1
Mu-type opioid receptor
CHEMBL2858
 IC50 7.09 7.09 82.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 18.0 - -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.4 nM 9.4 Compound was evaluated for binding affinity against [3H]- DAMGO labeled mu opioi... -
Mu-type opioid receptor Ki = 0.4 nM 9.4 Displacement of [3H]DAMGO from MOR in guinea pig brain membrane 23043264
Mu-type opioid receptor Ki = 0.41 nM 9.39 Displacement of [3H]DAMGO from mu opioid receptor expressed in CHO cells 19217280
Mu-type opioid receptor Ki = 0.41 nM 9.39 Displacement of [3H]naloxone from monocloned mu opioid receptor expressed in CHO... 19199782
Kappa-type opioid receptor Ki = 0.9 nM 9.05 Displacement of [3H]U69593 from KOR in guinea pig brain membrane 23043264
Kappa-type opioid receptor Ki = 0.9 nM 9.05 Compound was evaluated for binding affinity against [3H]- U-69593 labeled kappa1... -
Kappa-type opioid receptor Ki = 0.94 nM 9.03 Displacement of [3H]norBNI from kappa opioid receptor expressed in CHO cells 19217280
Kappa-type opioid receptor Ki = 0.94 nM 9.03 Displacement of [3H]norBNI from monocloned kappa opioid receptor expressed in CH... 19199782
Opioid receptor IC50 = 1.03 nM 8.99 The compound was tested for binding affinity against opioid receptor in rat brai... 3020246
Mu-type opioid receptor IC50 = 2.2 nM 8.66 Displacement of beta-[3H]FNA from mu opioid receptor in guinea pig brain membran... 19621878
Cavia porcellus IC50 = 4.8 nM 8.32 Tested for potent reversible agonist activity on electrically stimulated guinea ... 6245210
Mu-type opioid receptor IC50 = 4.8 nM 8.32 Inhibitory concentration against mu-opioid receptor in guinea pig ileum 8246236
Unchecked Ki = 7.7 nM 8.11 Displacement of [3H]Cl-DPDPE from DOR in guinea pig brain membrane 23043264
Delta-type opioid receptor Ki = 22.4 nM 7.65 Compound was evaluated for binding affinity against [3H]- Cl-DPDPE labeled Opioi... -
Delta-type opioid receptor Ki = 27.78 nM 7.56 Displacement of [3H]NTI from monocloned delta opioid receptor expressed in CHO c... 19199782
Delta-type opioid receptor Ki = 27.78 nM 7.56 Displacement of [3H]NTI from delta opioid receptor expressed in CHO cells 19217280
Mus musculus IC50 = 35.0 nM 7.46 Agonist activity measured on mouse vas deferens (MVD) 6310111
Kappa-type opioid receptor Ki = 66.5 nM 7.18 Compound was evaluated for binding affinity against [3H]- bremazocine labeled ka... -
Mu-type opioid receptor IC50 = 82.0 nM 7.09 Inhibitory concentration against mu-opioid receptor in mouse vas deferens 8246236
Opioid receptor IC50 = 82.0 nM 7.09 Compound was tested for agonist activity against opioid receptor in mouse vas de... 3020246

Literature References

PubMed DOI Target Context # Activities
8246236 10.1021/jm00075a023 Unchecked 10
3020246 10.1021/jm00160a013 Opioid receptors; mu/kappa/delta 6
6090663 10.1021/jm00376a018 Mu-type opioid receptor 6
6310111 10.1021/jm00363a005 Cavia porcellus 6
6310111 10.1021/jm00363a005 Mus musculus 5
3035177 10.1021/jm00389a014 Mus musculus 3
3035177 10.1021/jm00389a014 Cavia porcellus 3
8246236 10.1021/jm00075a023 Mus musculus 2
19217280 10.1016/j.bmcl.2008.12.093 Unchecked 2
19199782 10.1021/jm801272c Unchecked 2
- 10.1016/0960-894X(95)00583-F Kappa-type opioid receptor 2
19217280 10.1016/j.bmcl.2008.12.093 Mu-type opioid receptor 2
6090663 10.1021/jm00376a018 ADMET 2
6090663 10.1021/jm00376a018 Kappa-type opioid receptor 2
3020246 10.1021/jm00160a013 Opioid receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
8246236 10.1021/jm00075a023 Mu-type opioid receptor 2
6090663 10.1021/jm00376a018 Mus musculus 1
37413884 10.1016/j.ejmech.2023.115589 Mus musculus 1
11150174 10.1021/jm000317+ Opioid receptor 1

Data from ChEMBL 36 via Core Engine