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Compound Detail

CHEMBL13786

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CSCC[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 CHEMBL13786
Phase Preclinical
Structure Type BOTH
InChI Key YFGBQHOOROIVKG-FKBYEOEOSA-N
14
Targets
33
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

573.7
MW (Da)
-0.46
ALogP
8
HBA
7
HBD
199.9
PSA (Ų)
0.14
QED
2
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H35N5O7S
MW 573.67
Aromatic Rings 2
Heavy Atoms 40
NP-Likeness -0.21

Activity Summary

Ki 14 meas. best 8.96
IC50 11 meas. best 9.0
EC50 8 meas. best 9.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
EC50 9.8 7.6567 0.2 3
Delta-type opioid receptor
CHEMBL269
IC50 9.0 9.0 1.0 1
Delta-type opioid receptor
CHEMBL236
EC50 8.99 8.4367 1.0 3
Delta-type opioid receptor
CHEMBL236
Ki 8.96 8.83 1.1 2
Mu-type opioid receptor
CHEMBL233
Ki 8.82 8.4133 1.5 3
Mu-type opioid receptor
CHEMBL270
IC50 8.7 8.7 2.0 1
Delta-type opioid receptor
CHEMBL236
IC50 8.19 8.19 6.4 1
Mu-type opioid receptor
CHEMBL4354
Ki 8.16 8.16 6.9 1
Delta-type opioid receptor
CHEMBL269
Ki 8.14 8.14 7.3 1
Mu-type opioid receptor
CHEMBL233
IC50 7.89 7.89 13.0 1
Delta-type opioid receptor
CHEMBL3222
IC50 7.89 7.89 13.0 1
Mus musculus
CHEMBL375
IC50 7.89 7.89 13.0 1
Opioid receptor
CHEMBL2094129
IC50 7.75 7.14 18.0 3
Mu-type opioid receptor
CHEMBL270
Ki 7.7 7.63 20.0 2
Opioid receptor, delta 1b
CHEMBL4105711
Ki 7.35 7.35 45.0 1
Cavia porcellus
CHEMBL369
IC50 6.7 6.7 200.0 1
Mu-type opioid receptor
CHEMBL4354
IC50 6.7 6.7 200.0 1
Nociceptin receptor
CHEMBL5492
Ki 6.56 6.56 277.0 1
Mu-type opioid receptor
CHEMBL270
EC50 6.52 6.515 304.0 2
Mu opioid receptor-like OR2
CHEMBL3611961
Ki 6.17 6.17 684.0 1
Kappa-type opioid receptor
CHEMBL3952
Ki 5.35 5.35 4467.0 1
Unchecked
CHEMBL612545
Ki 4.3 4.3 49500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor EC50 = 0.16 nM 9.8 Agonist activity at human MOR expressed in CHO-K1 cells assessed as beta arresti... 37437352
Delta-type opioid receptor IC50 = 1.0 nM 9.0 Compound was evaluated for its binding affinity against enkephalin delta recepto... -
Delta-type opioid receptor EC50 = 1.03 nM 8.99 Agonist activity at human recombinant delta opioid receptor expressed in HEK293 ... 19362480
Delta-type opioid receptor EC50 = 1.03 nM 8.99 Agonist activity at human recombinant delta opioid receptor expressed in human H... 22197670
Delta-type opioid receptor Ki = 1.1 nM 8.96 Displacement of radiolabeled DPDPE-Cl from delta opioid receptor in Hartley guin... 16777416
Mu-type opioid receptor Ki = 1.5 nM 8.82 Displacement of [3H]-Diprenorphine from human MOR receptor expressed in CHO-K1 c... 36084534
Mu-type opioid receptor Ki = 2.0 nM 8.7 Displacement of [3H]-Diprenorphine from human MOR expressed in CHO-K1 cell membr... 37437352
Delta-type opioid receptor Ki = 2.0 nM 8.7 Displacement of [3H]diprenorphine from human cloned delta opioid receptor 17350835
Mu-type opioid receptor IC50 = 2.0 nM 8.7 Compound was evaluated for its binding affinity against enkephalin mu receptor u... -
Delta-type opioid receptor IC50 = 6.4 nM 8.19 Agonist activity at delta receptor (unknown origin) expressed in HEK293 cells as... 26465170
Mu-type opioid receptor Ki = 6.9 nM 8.16 Displacement of radiolabeled DAMGO from mu opioid receptor in Hartley guinea pig... 16777416
Delta-type opioid receptor Ki = 7.3 nM 8.14 Inhibition of [3H]DTLET binding torat brain membrane Opioid receptor delta 1 2845081
Mus musculus IC50 = 13.0 nM 7.89 Inhibitory potency evaluated against electrically evoked contractions of mouse v... 2845081
Delta-type opioid receptor IC50 = 13.0 nM 7.89 Inhibitory potency against delta Opioid receptor delta 1 in longitudinal muscle ... 6276540
Mu-type opioid receptor IC50 = 13.0 nM 7.89 Agonist activity at mu opioid receptor (unknown origin) expressed in HEK293 cell... 26465170
Opioid receptor IC50 = 18.0 nM 7.75 Compound was tested for its ability to displace [3H]naloxone from Opioid recepto... 6273560
Mu-type opioid receptor Ki = 19.0 nM 7.72 Displacement of [3H]diprenorphine from human cloned mu opioid receptor 17350835
Mu-type opioid receptor Ki = 20.0 nM 7.7 Compound was evaluated for binding affinity towards mu-specific opiate receptor ... 8064796
Mu-type opioid receptor Ki = 27.5 nM 7.56 Inhibition of [3H]DAGO binding to rat brain membrane Opioid receptor mu 1 2845081
Opioid receptor, delta 1b Ki = 45.0 nM 7.35 Displacement of [3H]DPN from zebrafish delta 1b opioid receptor expressed in HEK... 28284867

Literature References

PubMed DOI Target Context # Activities
16722632 10.1021/jm051026+ HBL 4
16722632 10.1021/jm051026+ HeLa 4
16722632 10.1021/jm051026+ HEp-2 4
16722632 10.1021/jm051026+ HT-29 4
16722632 10.1021/jm051026+ SW-620 4
16722632 10.1021/jm051026+ Caco-2 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
16722632 10.1021/jm051026+ MCF7 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
36084534 10.1016/j.ejmech.2022.114728 Nociceptin receptor 3
23822516 10.1021/jm4008592 Mu-type opioid receptor 3
36084534 10.1016/j.ejmech.2022.114728 Delta-type opioid receptor 3
36084534 10.1016/j.ejmech.2022.114728 Mu-type opioid receptor 3
37437352 10.1016/j.ejmech.2023.115608 Nociceptin receptor 3
37437352 10.1016/j.ejmech.2023.115608 Mu-type opioid receptor 3
17350835 10.1016/j.bmcl.2007.01.092 Mu-type opioid receptor 2
6273560 10.1021/jm00143a007 Opioid receptor 2
17350835 10.1016/j.bmcl.2007.01.092 Delta-type opioid receptor 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine