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Compound Detail

CHEMBL8234

ENKEPHALIN
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CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O

Basic Information

ChEMBL ID CHEMBL8234
Name ENKEPHALIN
Phase Preclinical
Structure Type BOTH
InChI Key URLZCHNOLZSCCA-VABKMULXSA-N
19
Targets
111
Activities
4
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

555.6
MW (Da)
-0.16
ALogP
7
HBA
7
HBD
199.9
PSA (Ų)
0.16
QED
2
Ro5 Violations
15
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H37N5O7
MW 555.63
Aromatic Rings 2
Heavy Atoms 40
NP-Likeness -0.01

Activity Summary

Ki 52 meas. best 9.15
IC50 40 meas. best 8.97
EC50 18 meas. best 10.1
Kd 1 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Delta-type opioid receptor
CHEMBL236
EC50 10.1 8.4213 0.1 8
Delta-type opioid receptor
CHEMBL236
Ki 9.15 8.5564 0.7 11
Delta-type opioid receptor
CHEMBL3222
IC50 8.97 8.3444 1.1 9
Mu-type opioid receptor
CHEMBL233
EC50 8.89 7.0683 1.3 6
Delta-type opioid receptor
CHEMBL269
Ki 8.85 8.5223 1.4 13
Mu-type opioid receptor
CHEMBL233
Ki 8.69 7.596 2.0 5
Mu-type opioid receptor
CHEMBL270
Ki 8.62 8.0533 2.4 12
Delta-type opioid receptor
CHEMBL3222
Ki 8.2 8.18 6.3 2
Proenkephalin-B
CHEMBL2227
Kd 8.15 8.15 7.1 1
Opioid receptor
CHEMBL2095192
IC50 8.08 7.6 8.4 2
Mus musculus
CHEMBL375
IC50 8.07 7.9586 8.6 7
Mu-type opioid receptor
CHEMBL4354
Ki 8.03 7.225 9.4 2
Mu-type opioid receptor
CHEMBL2858
IC50 8.03 7.81 9.4 3
Rattus norvegicus
CHEMBL376
IC50 7.96 7.96 11.0 1
Monoclonal antibody (mAb) 3E7
CHEMBL613295
IC50 7.76 7.76 17.5 1
Delta-type opioid receptor
CHEMBL269
IC50 7.75 7.75 17.7 1
Mu-type opioid receptor
CHEMBL270
IC50 7.3 7.3 49.8 1
Unchecked
CHEMBL612545
Ki 7.19 6.61 64.7 3
Opioid receptor homologue
CHEMBL4105897
Ki 7.14 7.14 73.0 1
Delta-type opioid receptor
CHEMBL3222
EC50 7.13 7.13 74.0 1
Kappa-type opioid receptor
CHEMBL237
EC50 7.1 7.1 80.0 3
Unchecked
CHEMBL612545
IC50 7.0 7.0 100.0 1
Mu-type opioid receptor
CHEMBL4354
IC50 6.99 6.6733 103.0 6
Opioid receptor, delta 1b
CHEMBL4105711
Ki 6.76 6.76 175.0 1
Cavia porcellus
CHEMBL369
IC50 6.67 6.6186 213.0 7
Mu opioid receptor-like OR2
CHEMBL3611961
Ki 5.88 5.88 1317.0 1
Kappa-type opioid receptor
CHEMBL3952
Ki 5.34 5.34 4570.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.02 5.02 9500.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 1.53 nM Cavia porcellus
Ke 5.86 nM Mus musculus
Ke 1.53 nM Cavia porcellus
Ke 1.53 nM Cavia porcellus
Ke 1.53 nM Cavia porcellus
Ke 21.4 nM Mus musculus
T1/2 13.5 hr Homo sapiens
T1/2 0.0115 hr Homo sapiens
T1/2 2.167 hr Homo sapiens
T1/2 0.08333 hr Rattus norvegicus
T1/2 0.07667 hr Rattus norvegicus
T1/2 0.08333 hr Rattus norvegicus
T1/2 0.2 hr Homo sapiens
T1/2 0.0115 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Delta-type opioid receptor EC50 = 0.08 nM 10.1 Agonist activity at human delta opioid receptor expressed in CHO-K1 cells assess... 32686940
Delta-type opioid receptor EC50 = 0.08 nM 10.1 Agonist activity at delta opioid receptor (unknown origin) expressed in CHO cell... 31377035
Delta-type opioid receptor Ki = 0.7 nM 9.15 In vitro binding affinity to human Opioid receptor delta 1 on CHO cell membranes... 12747782
Delta-type opioid receptor EC50 = 1.0 nM 9.0 Agonist activity at human DOR expressed in CHO cells assessed as reduction in ER... 36099150
Delta-type opioid receptor IC50 = 1.07 nM 8.97 Agonist activity at FLAG-tagged mouse delta opioid receptor expressed in human H... 34825191
Delta-type opioid receptor IC50 = 1.072 nM 8.97 Agonist activity at FLAG-tagged mouse delta opioid receptor expressed in human H... 34825191
Delta-type opioid receptor Ki = 1.122 nM 8.95 Displacement of [3H]DPDPE from human delta opioid receptor expressed in CHO cell... 34825191
Delta-type opioid receptor Ki = 1.12 nM 8.95 Displacement of [3H]DPDPE from human delta opioid receptor expressed in CHO cell... 34825191
Delta-type opioid receptor Ki = 1.2 nM 8.92 Displacement of [3H]-DPDPE from human delta opioid receptor expressed in CHO-K1 ... 33326237
Delta-type opioid receptor Ki = 1.259 nM 8.9 Displacement of [3H]-DPDPE from human delta opioid receptor expressed in CHO-K1 ... 33326237
Delta-type opioid receptor IC50 = 1.259 nM 8.9 Agonist activity at mouse FLAG-tagged delta opioid receptor expressed in HEK293 ... 33326237
Mu-type opioid receptor EC50 = 1.3 nM 8.89 Agonist activity at mu opioid receptor (unknown origin) expressed in CHO cells 31377035
Mu-type opioid receptor EC50 = 1.3 nM 8.89 Agonist activity at human mu opioid receptor expressed in CHO-K1 cells assessed ... 32686940
Delta-type opioid receptor Ki = 1.43 nM 8.85 Binding affinity was determined towards Opioid receptor delta 1 in rat brain syn... 11212102
Delta-type opioid receptor IC50 = 1.4 nM 8.85 Agonist activity at mouse FLAG-tagged delta opioid receptor expressed in HEK293 ... 33326237
Delta-type opioid receptor Ki = 1.5 nM 8.82 The compound was tested for the ability to displace delta-receptor specific radi... 2536436
Mu-type opioid receptor Ki = 2.042 nM 8.69 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cell me... 34825191
Mu-type opioid receptor Ki = 2.07 nM 8.68 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cell me... 34825191
Mu-type opioid receptor Ki = 2.42 nM 8.62 Binding affinity was determined towards Opioid receptor mu 1 in rat brain synapt... 11212102
Mu-type opioid receptor Ki = 2.53 nM 8.6 Binding affinity was determined by displacement of [3H]- DSLET at Opioid recepto... 10691681

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 346
- 10.6019/CHEMBL4689842 Fibroblast 345
- 10.6019/CHEMBL4689842 U2OS 344
6319698 10.1021/jm00368a002 Unchecked 10
25901762 10.1021/acs.jmedchem.5b00007 Delta-type opioid receptor 8
34825191 10.1039/D1MD00025J Delta-type opioid receptor 7
12467635 10.1016/s0960-894x(02)00847-8 Rattus norvegicus 7
34825191 10.1039/D1MD00025J Mu-type opioid receptor 7
6296388 10.1021/jm00354a008 Delta-type opioid receptor 5
32901477 10.1021/acs.jmedchem.9b02057 Mu-type opioid receptor 5
33326237 10.1021/acs.jnatprod.0c01036 Delta-type opioid receptor 5
32901477 10.1021/acs.jmedchem.9b02057 Delta-type opioid receptor 5
32686940 10.1021/acs.jmedchem.0c00530 Delta-type opioid receptor 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
1331451 10.1021/jm00099a025 Delta-type opioid receptor 4
1331451 10.1021/jm00099a025 Mu-type opioid receptor 4
6296388 10.1021/jm00354a008 Mu-type opioid receptor 4
8164255 10.1021/jm00034a011 Mu-type opioid receptor 3
26288687 10.1021/acsmedchemlett.5b00126 Unchecked 3
10479285 10.1021/jm980724+ Mu-type opioid receptor 3

Data from ChEMBL 36 via Core Engine