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Compound Detail

CHEMBL316446

ENDOMORPHIN-1
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NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)Cc1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL316446
Name ENDOMORPHIN-1
Phase Preclinical
Structure Type BOTH
InChI Key ZEXLJFNSKAHNFH-SYKYGTKKSA-N
13
Targets
81
Activities
3
Assay Types
24
PK Parameters
20
Publications
0
Known Names

Molecular Properties

610.7
MW (Da)
1.67
ALogP
6
HBA
6
HBD
183.6
PSA (Ų)
0.14
QED
2
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 C34H38N6O5
MW 610.72
Aromatic Rings 4
Heavy Atoms 45
NP-Likeness -0.15

Activity Summary

Ki 48 meas. best 9.8
IC50 24 meas. best 9.37
EC50 9 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL270
 Ki 9.8 8.6678 0.2 18
Mu-type opioid receptor
CHEMBL233
 Ki 9.54 8.8213 0.3 8
Mu-type opioid receptor
CHEMBL270
 IC50 9.37 8.788 0.4 5
Mu-type opioid receptor
CHEMBL233
 IC50 8.49 7.84 3.2 3
Mu-type opioid receptor
CHEMBL4354
 IC50 8.39 7.4183 4.0 6
Ileum
CHEMBL613680
 IC50 8.06 8.06 8.7 1
Mu-type opioid receptor
CHEMBL233
 EC50 7.85 7.684 14.0 5
Unchecked
CHEMBL612545
 IC50 7.72 7.72 19.1 1
Delta-type opioid receptor
CHEMBL3222
 IC50 7.58 7.3075 26.0 4
Unchecked
CHEMBL612545
 Ki 7.48 5.92 32.8 3
Mu-type opioid receptor
CHEMBL2858
 IC50 7.44 7.44 36.3 1
Vas deferens
CHEMBL613599
 IC50 7.3 7.3 50.1 1
Kappa-type opioid receptor
CHEMBL3614
 Ki 7.28 7.28 52.7 1
Mu-type opioid receptor
CHEMBL270
 EC50 6.98 6.88 104.0 2
Delta-type opioid receptor
CHEMBL269
 Ki 6.24 5.606 575.0 10
Delta-type opioid receptor
CHEMBL236
 EC50 6.03 6.03 932.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 5.69 5.69 2048.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 5.63 5.46 2354.0 2
Delta-type opioid receptor
CHEMBL236
 Ki 5.56 5.37 2765.0 5
Delta-type opioid receptor
CHEMBL269
 IC50 5.45 5.45 3580.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 270.75 - Mus musculus
AUC 692.99 - Mus musculus
T1/2 0.08167 hr Rattus norvegicus
T1/2 0.1003 hr Rattus norvegicus
T1/2 0.08333 hr Homo sapiens
T1/2 4.9 hr Rattus norvegicus
T1/2 0.105 hr Rattus norvegicus
T1/2 0.045 hr Homo sapiens
T1/2 0.09333 hr Homo sapiens
T1/2 0.2817 hr Mus musculus
T1/2 0.09833 hr Homo sapiens
T1/2 0.03833 hr Rattus norvegicus
T1/2 0.1015 hr Mus musculus
T1/2 0.3923 hr Mus musculus
T1/2 0.09 hr Mus musculus
T1/2 0.225 hr Mus musculus
T1/2 0.1817 hr Mus musculus
T1/2 0.2817 hr Mus musculus
T1/2 0.29 hr Mus musculus
T1/2 0.1717 hr Mus musculus
T1/2 5.0 hr Mus musculus
T1/2 5.0 hr Mus musculus
T1/2 0.08333 hr Rattus norvegicus
T1/2 0.08333 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.16 nM 9.8 Inhibition of [3H]-DAMGO binding to Opioid receptor mu 1 of rat brain membranes 15456262
Mu-type opioid receptor Ki = 0.16 nM 9.8 Binding affinity towards Opioid receptor mu 1 by displacing [3H]DAMGO in rat bra... 12036366
Mu-type opioid receptor Ki = 0.29 nM 9.54 Displacement of [3H]DAMGO from mu-opioid receptor expressed in CHOK1 cells after... 22680612
Mu-type opioid receptor IC50 = 0.43 nM 9.37 Displacement of [3H]DAMGO from mu opioid receptor in Wistar rat brain membrane 19435668
Mu-type opioid receptor IC50 = 0.5 nM 9.3 Inhibition of [3H]DAMGO binding to Opioid receptor mu 1 of rat brain membranes 15456262
Mu-type opioid receptor IC50 = 0.5 nM 9.3 Inhibitory activity against [3H]DAMGO binding to Opioid receptor mu 1 in rat bra... 12036366
Mu-type opioid receptor Ki = 0.56 nM 9.25 Displacement of [3H]DAMGO from mu opioid receptor in rat brain P2 synaptosome 17142049
Mu-type opioid receptor Ki = 0.7 nM 9.15 Displacement of [3H]DAMGO from rat cortical MOR by liquid scintillation counting... 26789491
Mu-type opioid receptor Ki = 0.74 nM 9.13 Displacement of [3H]DAMGO from mu opioid receptor in Wistar rat brain 18572932
Mu-type opioid receptor Ki = 0.76 nM 9.12 Displacement of [3H]DAMGO from MOP receptor expressed in CHO-K1 cells after over... 23022277
Mu-type opioid receptor Ki = 1.11 nM 8.96 Displacement of [3H]DAMGO from mu opioid receptor in human SHSY5Y cells 18468445
Mu-type opioid receptor Ki = 1.15 nM 8.94 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane 18468445
Mu-type opioid receptor Ki = 1.45 nM 8.84 Displacement of [3H]DAMGO from mu opioid receptor in human SH-SY5Y cells 18329886
Mu-type opioid receptor Ki = 1.6 nM 8.8 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane homogena... 21287991
Mu-type opioid receptor Ki = 1.62 nM 8.79 Displacement of [3H]endomorphin-2 from Opioid receptor mu 1 of rat brain membran... 14736254
Mu-type opioid receptor IC50 = 1.89 nM 8.72 Displacement of [3H]DAGO from mu opioid receptor in rat brain membrane 17395470
Mu-type opioid receptor Ki = 2.1 nM 8.68 Displacement of [3H]endomorphin-2 from mu opioid receptor in Wistar rat brain 18572932
Mu-type opioid receptor Ki = 2.6 nM 8.59 Displacement of [3H]DAMGO from FLAG-tagged mu opioid receptor expressed in HEK29... 22724433
Mu-type opioid receptor Ki = 2.6 nM 8.59 Displacement of [3H]DAMGO from human cloned mu-opioid receptor by radioligand bi... 36206553
Mu-type opioid receptor Ki = 2.6 nM 8.59 Displacement of [3H]-DAMGO from mu opioid receptor (unknown origin) transfected ... 26403932

Literature References

PubMed DOI Target Context # Activities
34781680 10.1021/acs.jmedchem.1c01631 Mus musculus 14
22724433 10.1021/jm300664y Mu-type opioid receptor 8
34781680 10.1021/acs.jmedchem.1c01631 ADMET 6
26403932 10.1016/j.bmcl.2015.09.025 Mus musculus 6
32199689 10.1016/j.bmc.2020.115438 Mus musculus 5
34995453 10.1021/acs.jmedchem.0c01915 ADMET 4
26288687 10.1021/acsmedchemlett.5b00126 Unchecked 4
18468445 10.1016/j.bmc.2008.04.020 Mu-type opioid receptor 4
21287991 10.1021/jm101515v Mu-type opioid receptor 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
18572932 10.1021/jm800223t Mu-type opioid receptor 4
14736254 10.1021/jm0310028 Mu-type opioid receptor 4
17266203 10.1021/jm060998u Mu-type opioid receptor 3
17266203 10.1021/jm060998u Delta-type opioid receptor 3
17266203 10.1021/jm060998u Mus musculus 3
22680612 10.1021/jm300418d Mu-type opioid receptor 3
14736254 10.1021/jm0310028 Rattus norvegicus 3
26403932 10.1016/j.bmcl.2015.09.025 Mu-type opioid receptor 3
34781680 10.1021/acs.jmedchem.1c01631 Mu-type opioid receptor 3
22724433 10.1021/jm300664y Delta-type opioid receptor 3

Data from ChEMBL 36 via Core Engine