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Compound Detail

CHEMBL281786

DIPRENORPHINE
🧪 Phase II
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🧪 Phase II
CO[C@]12CC[C@@]3(C[C@@H]1C(C)(C)O)[C@H]1Cc4ccc(O)c5c4[C@@]3(CCN1CC1CC1)[C@H]2O5
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL281786
Name DIPRENORPHINE
Phase Phase II
Structure Type MOL
InChI Key OIJXLIIMXHRJJH-KNLIIKEYSA-N

Known Names

Diprenorfin Diprenorfina Diprenorphine M-5050 M. 5050 M5050 Revivon
10
Targets
22
Activities
3
Assay Types
1
PK Parameters
20
Publications
7
Known Names

Molecular Properties

425.6
MW (Da)
3.39
ALogP
5
HBA
2
HBD
62.2
PSA (Ų)
0.77
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C26H35NO4
MW 425.57
Aromatic Rings 1
Heavy Atoms 31
NP-Likeness 1.76

Activity Summary

Ki 12 meas. best 10.7
IC50 5 meas. best 9.17
Kd 5 meas. best 10.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 10.7 9.652 0.0 5
Kappa-type opioid receptor
CHEMBL3614
 Kd 10.54 10.39 0.0 4
Mu-type opioid receptor
CHEMBL233
 Ki 10.15 9.762 0.1 5
Unchecked
CHEMBL612545
 Ki 9.66 9.66 0.2 1
Delta-type opioid receptor
CHEMBL236
 Ki 9.64 9.64 0.2 1
Delta-type opioid receptor
CHEMBL236
 IC50 9.17 9.17 0.7 1
Mu-type opioid receptor
CHEMBL4354
 IC50 9.15 9.15 0.7 1
Rattus norvegicus
CHEMBL376
 Kd 9.0 9.0 1.0 1
Opioid receptors; mu/kappa/delta
CHEMBL2095181
 IC50 8.89 8.89 1.3 1
Mu-type opioid receptor
CHEMBL3041
 IC50 8.85 8.85 1.4 1
Kappa-type opioid receptor
CHEMBL3952
 IC50 8.74 8.74 1.8 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 0.13 - -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.02 nM 10.7 Binding affinity to human cloned kappa opioid receptor expressed in HEK293 cells... 24933507
Kappa-type opioid receptor Kd = 0.029 nM 10.54 Dissociation constant against wild type EL-2 Opioid receptor kappa 1 expressed i... 10753461
Kappa-type opioid receptor Kd = 0.038 nM 10.42 Dissociation constant against E203Q,D204N,D206N,E209Q EL-2 Opioid receptor kappa... 10753461
Kappa-type opioid receptor Kd = 0.05 nM 10.3 Dissociation constant against E203Q,D204N,D206N EL-2 Opioid receptor kappa 1 exp... 10753461
Kappa-type opioid receptor Kd = 0.05 nM 10.3 Dissociation constant against D216N,D217N,E218Q EL-2 Opioid receptor kappa 1 exp... 10753461
Mu-type opioid receptor Ki = 0.07 nM 10.15 Binding affinity to human cloned mu opioid receptor expressed in CHO cells by ra... 24933507
Mu-type opioid receptor Ki = 0.123 nM 9.91 Displacement of 2-((1E,3E,5E)-5-(1-Ethyl-3,3-dimethyl-5-sulfoindolin-2-ylidene)-... 26632862
Mu-type opioid receptor Ki = 0.1995 nM 9.7 Displacement of [3H]DAMGO from human MOR expressed in HEK293 cells preincubated ... 26632862
Unchecked Ki = 0.22 nM 9.66 Binding affinity (Ki) was determined towards Opioid receptors by competition wit... 2158564
Delta-type opioid receptor Ki = 0.23 nM 9.64 Binding affinity to human cloned delta opioid receptor expressed in CHO cells by... 24933507
Mu-type opioid receptor Ki = 0.27 nM 9.57 Binding affinity using [3H]diprenorphine as the radioligand against wild-type Op... 10780914
Kappa-type opioid receptor Ki = 0.28 nM 9.55 Binding affinity using [3H]diprenorphine as the radioligand against wild-type Op... 10780914
Mu-type opioid receptor Ki = 0.33 nM 9.48 Binding affinity using [3H]diprenorphine as the radioligand against K303E Opioid... 10780914
Kappa-type opioid receptor Ki = 0.37 nM 9.43 Binding affinity using [3H]diprenorphine as the radioligand against E297K mutant... 10780914
Kappa-type opioid receptor Ki = 0.38 nM 9.42 Binding affinity using [3H]diprenorphine as the radioligand against E297A mutant... 10780914
Delta-type opioid receptor IC50 = 0.68 nM 9.17 Inhibition of Opioid receptor delta 1 by displacing 1 nM [3H]DPDPE in guinea pig... 1335078
Kappa-type opioid receptor Ki = 0.69 nM 9.16 Displacement of [3H]diprenorphine from human KOR expressed in HEK293T cell membr... 30543421
Mu-type opioid receptor IC50 = 0.71 nM 9.15 Inhibition of opioid receptor mu by displacing 1 nM [3H]DAGO in guinea pig brain... 1335078
Rattus norvegicus Kd = 1.0 nM 9.0 Binding of [3H]diprenorphine to rat brain membranes was evaluated and the dissoc... 2158564
Opioid receptors; mu/kappa/delta IC50 = 1.3 nM 8.89 Inhibition of total opioid receptor by displacing 0.5 nM [3H]bremazocine in guin... 1335078

Literature References

PubMed DOI Target Context # Activities
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
10753461 10.1021/jm990583r Kappa-type opioid receptor 4
10780914 10.1021/jm000059g Kappa-type opioid receptor 3
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B7 3
26632862 10.1021/acs.jmedchem.5b01664 Mu-type opioid receptor 2
10780914 10.1021/jm000059g Mu-type opioid receptor 2
17367120 10.1021/jm0612463 Delta-type opioid receptor 2
2165166 10.1021/jm00170a038 Mu-type opioid receptor 1
2158564 10.1021/jm00167a031 No relevant target 1
24933507 10.1021/jm500503k Kappa-type opioid receptor 1
24933507 10.1021/jm500503k Delta-type opioid receptor 1
24933507 10.1021/jm500503k Mu-type opioid receptor 1
2158564 10.1021/jm00167a031 Unchecked 1
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1A3 1
1335078 10.1021/jm00102a012 Mu-type opioid receptor 1
2158564 10.1021/jm00167a031 Rattus norvegicus 1
6312042 10.1021/jm00364a001 ADMET 1
6312042 10.1021/jm00364a001 Unchecked 1
1335078 10.1021/jm00102a012 Opioid receptors; mu/kappa/delta 1
1335078 10.1021/jm00102a012 Delta-type opioid receptor 1

Data from ChEMBL 36 via Core Engine