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Compound Detail

CHEMBL333357

ENDOMORPHIN 2
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NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)Cc1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL333357
Name ENDOMORPHIN 2
Phase Preclinical
Structure Type BOTH
InChI Key XIJHWXXXIMEHKW-LJWNLINESA-N
17
Targets
116
Activities
3
Assay Types
18
PK Parameters
20
Publications
0
Known Names

Molecular Properties

571.7
MW (Da)
1.19
ALogP
6
HBA
5
HBD
167.8
PSA (Ų)
0.22
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C32H37N5O5
MW 571.68
Aromatic Rings 3
Heavy Atoms 42
NP-Likeness -0.14

Activity Summary

Ki 61 meas. best 9.31
IC50 40 meas. best 9.16
EC50 15 meas. best 10.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 EC50 10.4 8.25 0.0 12
Mu-type opioid receptor
CHEMBL270
 Ki 9.31 8.5342 0.5 24
Mu-type opioid receptor
CHEMBL233
 Ki 9.16 8.5717 0.7 6
Mu-type opioid receptor
CHEMBL270
 IC50 9.16 9.0029 0.7 7
Mu-type opioid receptor
CHEMBL4354
 IC50 8.33 7.7646 4.7 13
Cavia porcellus
CHEMBL369
 IC50 8.24 8.175 5.8 2
Unchecked
CHEMBL612545
 Ki 8.09 6.0833 8.2 3
Substance-P receptor
CHEMBL4027
 Ki 8.06 8.06 8.7 2
Mu-opioid receptor
CHEMBL5430
 IC50 8.02 8.02 9.7 1
Kappa-type opioid receptor
CHEMBL3614
 Ki 7.97 7.97 10.6 1
Ileum
CHEMBL613680
 IC50 7.95 7.95 11.3 1
Delta-type opioid receptor
CHEMBL3222
 IC50 7.82 6.9289 15.3 9
Mus musculus
CHEMBL375
 IC50 7.82 7.14 15.3 2
Mu-type opioid receptor
CHEMBL2858
 IC50 7.78 7.7 16.8 2
Vas deferens
CHEMBL613599
 IC50 7.37 7.37 42.9 1
Mu-type opioid receptor
CHEMBL270
 EC50 7.11 6.7333 78.0 3
Kappa-type opioid receptor
CHEMBL237
 Ki 5.95 5.615 1136.0 2
Delta-type opioid receptor
CHEMBL269
 Ki 5.64 5.1863 2300.0 16
Kappa-type opioid receptor
CHEMBL3952
 Ki 5.57 5.34 2708.0 2
Delta-type opioid receptor
CHEMBL236
 Ki 5.47 5.245 3385.0 4
Delta-type opioid receptor
CHEMBL269
 IC50 4.99 4.99 10300.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 120.0 /M/s -
T1/2 0.06333 hr Rattus norvegicus
T1/2 0.3283 hr Mus musculus
T1/2 0.06333 hr Rattus norvegicus
T1/2 0.08 hr Rattus norvegicus
T1/2 3.8 hr Rattus norvegicus
T1/2 0.095 hr Rattus norvegicus
T1/2 0.2383 hr Rattus norvegicus
T1/2 0.09667 hr Rattus norvegicus
T1/2 0.1 hr Rattus norvegicus
T1/2 0.0125 hr Rattus norvegicus
T1/2 0.2117 hr Mus musculus
T1/2 0.2067 hr Mus musculus
T1/2 0.2583 hr Mus musculus
T1/2 0.1483 hr Mus musculus
T1/2 0.1367 hr Mus musculus
T1/2 0.0125 hr Rattus norvegicus
T1/2 0.265 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor EC50 = 0.04 nM 10.4 Antagonist activity at mu opioid receptor expressed in CHO cells assessed as rel... 18207400
Mu-type opioid receptor EC50 = 0.04 nM 10.4 Activity at mu opioid receptor assessed as increase in calcium level in CHO cell... 17266203
Mu-type opioid receptor Ki = 0.49 nM 9.31 Displacement of [3H]DAMGO from MOR in Wistar rat brain homogenates by liquid sci... 26785295
Mu-type opioid receptor Ki = 0.69 nM 9.16 Binding affinity to mu opioid receptor 16789756
Mu-type opioid receptor Ki = 0.69 nM 9.16 Displacement of [3H]DAMGO from Wistar rat brain membrane MOP 34995453
Mu-type opioid receptor Ki = 0.69 nM 9.16 Inhibition of [3H]DAMGO binding to mu-Opioid receptor 15658871
Mu-type opioid receptor Ki = 0.69 nM 9.16 Binding affinity against rat brain Opioid receptor mu 1 using [3H]DAMGO radiolig... 15214786
Mu-type opioid receptor IC50 = 0.69 nM 9.16 Displacement of [3H]DAMGO from mu opioid receptor in Wistar rat brain membrane 19435668
Mu-type opioid receptor IC50 = 0.79 nM 9.1 Displacement of [3H]DAMGO from mu opioid receptor in Wistar rat brain membranes ... 26005537
Mu-type opioid receptor IC50 = 0.79 nM 9.1 Displacement of [3H]DAMGO from MOR in rat brain membranes 25047937
Mu-type opioid receptor IC50 = 0.79 nM 9.1 Displacement of [3H]DAMGO from MOR in Wistar rat brain membranes by liquid scint... 25456075
Mu-type opioid receptor IC50 = 0.79 nM 9.1 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes 18207400
Mu-type opioid receptor IC50 = 0.99 nM 9.0 Displacement of [3H]DAMGO from Wistar rat mu opioid receptor by liquid scintilla... 22047797
Mu-type opioid receptor Ki = 1.3 nM 8.89 Displacement of [3H]DAMGO from mu opioid receptor in Wistar rat brain 18572932
Mu-type opioid receptor Ki = 1.3 nM 8.89 Displacement of [3H]endomorphin-2 from mu opioid receptor in Wistar rat brain 18572932
Mu-type opioid receptor Ki = 1.33 nM 8.88 Displacement of [3H]DAMGO from mu opioid receptor in rat brain P2 synaptosome 17142049
Mu-type opioid receptor Ki = 1.33 nM 8.88 Displacement of [3H]DAMGO from mu opioid receptor in Sprague-Dawley rat brain P2... 17497839
Mu-type opioid receptor Ki = 1.33 nM 8.88 Binding affinity to mu opioid receptor (unknown origin) 24613457
Mu-type opioid receptor Ki = 1.35 nM 8.87 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane homogena... 21287991
Mu-type opioid receptor Ki = 1.4 nM 8.85 Displacement of [3H]DAMGO from mu opioid receptor in Wistar rat brain membranes 22957923

Literature References

PubMed DOI Target Context # Activities
34781680 10.1021/acs.jmedchem.1c01631 Mus musculus 14
22047797 10.1016/j.bmc.2011.10.040 Mus musculus 6
18207400 10.1016/j.bmcl.2008.01.009 Mus musculus 6
18062664 10.1021/jm7010222 Mu-type opioid receptor 6
34781680 10.1021/acs.jmedchem.1c01631 ADMET 6
22724433 10.1021/jm300664y Mu-type opioid receptor 5
22957923 10.1021/jm300836n Mu-type opioid receptor 5
32199689 10.1016/j.bmc.2020.115438 Mus musculus 5
18572932 10.1021/jm800223t Mu-type opioid receptor 4
21287991 10.1021/jm101515v Mu-type opioid receptor 4
19435668 10.1016/j.bmc.2009.04.046 Mus musculus 4
14736254 10.1021/jm0310028 Mu-type opioid receptor 4
30626554 10.1016/j.bmc.2019.01.003 Mu-type opioid receptor 4
16682191 10.1016/j.bmcl.2006.04.063 Mus musculus 4
34995453 10.1021/acs.jmedchem.0c01915 ADMET 4
15780619 10.1016/j.bmcl.2005.02.021 Delta-type opioid receptor 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
17266203 10.1021/jm060998u Delta-type opioid receptor 3
18207400 10.1016/j.bmcl.2008.01.009 Delta-type opioid receptor 3
17266203 10.1021/jm060998u Mus musculus 3

Data from ChEMBL 36 via Core Engine