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Compound Detail

CHEMBL386272

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COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(NC(=O)/C=C/c5ccc(Cl)cc5)[C@@H](C2)N(CC2CC2)CC[C@]314
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL386272
Phase Preclinical
Structure Type MOL
InChI Key LZSMGMMAKBCSRL-WDJVXPEUSA-N
3
Targets
19
Activities
3
Assay Types
10
PK Parameters
19
Publications
0
Known Names

Molecular Properties

519.0
MW (Da)
4.32
ALogP
5
HBA
1
HBD
67.9
PSA (Ų)
0.58
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H31ClN2O4
MW 519.04
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness 0.49

Activity Summary

Ki 15 meas. best 9.34
IC50 3 meas. best 9.01
EC50 1 meas. best 7.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.34 8.524 0.5 5
Mu-type opioid receptor
CHEMBL233
 IC50 9.01 9.01 1.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 8.35 8.326 4.5 5
Delta-type opioid receptor
CHEMBL236
 IC50 8.14 8.14 7.2 1
Kappa-type opioid receptor
CHEMBL237
 IC50 8.01 8.01 9.8 1
Kappa-type opioid receptor
CHEMBL237
 Ki 7.8 7.742 16.0 5
Mu-type opioid receptor
CHEMBL233
 EC50 7.75 7.75 17.8 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 6.37 nM Cercopithecidae
Ke 9.8 nM Homo sapiens
Ke 7.2 nM Homo sapiens
Ke 0.97 nM Homo sapiens
Ke 0.97 nM Homo sapiens
Ke 7.2 nM Homo sapiens
Ke 9.8 nM Homo sapiens
Ke 0.97 nM Homo sapiens
Ke 7.16 nM Homo sapiens
Ke 9.81 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.46 nM 9.34 Displacement of radioligand [3H]- DAMGO on Opioid receptor mu 1 in monkey brain ... 10966754
Mu-type opioid receptor IC50 = 0.97 nM 9.01 Activity at human recombinant mu opioid receptor expressed in CHO cells assessed... 17004724
Delta-type opioid receptor Ki = 4.5 nM 8.35 Displacement of radioligand [3H]- DPDPE on Opioid receptor delta 1 in monkey bra... 10966754
Delta-type opioid receptor Ki = 4.79 nM 8.32 Displacement of [3H]Cl-DPDPE from human recombinant delta opioid receptor expres... 17004724
Delta-type opioid receptor Ki = 4.79 nM 8.32 Displacement of [3H]DPDPE from human recombinant delta opioid receptor expressed... 19842669
Mu-type opioid receptor Ki = 4.78 nM 8.32 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 19842669
Delta-type opioid receptor Ki = 4.8 nM 8.32 Displacement of [3H]DPDPE from human delta opioid receptor expressed in CHO cell... 19253983
Mu-type opioid receptor Ki = 4.8 nM 8.32 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells 19253983
Mu-type opioid receptor Ki = 4.78 nM 8.32 Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in... 17004724
Mu-type opioid receptor Ki = 4.78 nM 8.32 Displacement of [3H]DAMGO from human recombinant MOR expressed in CHO cells 16913723
Delta-type opioid receptor Ki = 4.8 nM 8.32 Displacement of [3H]Cl-DPDPE from human recombinant DOR expressed in CHO cells 16913723
Delta-type opioid receptor IC50 = 7.16 nM 8.14 Activity at human recombinant delta opioid receptor expressed in CHO cells asses... 17004724
Kappa-type opioid receptor IC50 = 9.81 nM 8.01 Activity at human recombinant kappa opioid receptor expressed in CHO cells asses... 17004724
Kappa-type opioid receptor Ki = 16.0 nM 7.8 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce... 19253983
Kappa-type opioid receptor Ki = 16.4 nM 7.79 Displacement of [3H]U-69593 from human recombinant KOR expressed in CHO cells 16913723
Kappa-type opioid receptor Ki = 16.4 nM 7.79 Displacement of [3H]U-69593 from human recombinant kappa opioid receptor express... 17004724
Kappa-type opioid receptor Ki = 16.4 nM 7.79 Displacement of [3H]U69593 from human recombinant kappa opioid receptor expresse... 19842669
Mu-type opioid receptor EC50 = 17.8 nM 7.75 Agonist activity at human mu opioid receptor expressed in CHO cells assessed as ... 19253983
Kappa-type opioid receptor Ki = 29.0 nM 7.54 Displacement of radioligand [3H]- U-69,593 on Opioid receptor kappa 1 in monkey ... 10966754

Literature References

PubMed DOI Target Context # Activities
16913723 10.1021/jm0604777 Mus musculus 5
9719602 10.1021/jm9810248 Mus musculus 4
19253983 10.1021/jm8012272 Mu-type opioid receptor 4
19253983 10.1021/jm8012272 Delta-type opioid receptor 3
17004724 10.1021/jm060595u Mu-type opioid receptor 3
17004724 10.1021/jm060595u Kappa-type opioid receptor 3
17004724 10.1021/jm060595u Delta-type opioid receptor 3
19842669 10.1021/jm901074a Kappa-type opioid receptor 2
19842669 10.1021/jm901074a Delta-type opioid receptor 2
19842669 10.1021/jm901074a Mu-type opioid receptor 2
19253983 10.1021/jm8012272 Kappa-type opioid receptor 2
16913723 10.1021/jm0604777 Mu-type opioid receptor 2
16913723 10.1021/jm0604777 Delta-type opioid receptor 2
16913723 10.1021/jm0604777 Kappa-type opioid receptor 2
10966754 10.1021/jm0009641 Mu-type opioid receptor 2
17004724 10.1021/jm060595u Opioid receptors; mu & delta 1
17004724 10.1021/jm060595u Opioid receptors; mu & kappa 1
10966754 10.1021/jm0009641 Kappa-type opioid receptor 1
10966754 10.1021/jm0009641 Delta-type opioid receptor 1

Data from ChEMBL 36 via Core Engine