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Compound Detail

CHEMBL301160

BUTORPHAN
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Oc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(CC1CCC1)CC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL301160
Name BUTORPHAN
Phase Preclinical
Structure Type MOL
InChI Key YSTAPDGDOHWKQR-CEWLAPEOSA-N
5
Targets
74
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

311.5
MW (Da)
4.25
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.88
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H29NO
MW 311.47
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 1.03

Activity Summary

Ki 53 meas. best 10.15
EC50 15 meas. best 8.89
IC50 6 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL3952
 Ki 10.15 10.13 0.1 3
Kappa-type opioid receptor
CHEMBL237
 Ki 10.14 10.1027 0.1 15
Mu-type opioid receptor
CHEMBL233
 Ki 9.92 9.6587 0.1 15
Mu-type opioid receptor
CHEMBL4354
 Ki 9.92 9.8267 0.1 3
Delta-type opioid receptor
CHEMBL236
 Ki 8.89 8.3465 1.3 17
Kappa-type opioid receptor
CHEMBL237
 EC50 8.89 8.89 1.3 8
Mu-type opioid receptor
CHEMBL233
 EC50 8.8 8.8 1.6 7
Mu-type opioid receptor
CHEMBL233
 IC50 7.7 7.7 20.0 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.07 nM 10.15 Binding affinity towards Opioid receptor kappa 1 in guinea pig brain membranes u... 11591513
Kappa-type opioid receptor Ki = 0.073 nM 10.14 Binding affinity towards Opioid receptor kappa 1 by displacing the radioligand [... 10633042
Kappa-type opioid receptor Ki = 0.073 nM 10.14 Binding affinity to kappa opioid receptor (unknown origin) 26656913
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 18674902
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce... 20144870
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 19634902
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 19928862
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 21351746
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69563 from human kappa-opioid receptor expressed in CHO cel... 21482470
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]-U69,593 from human kappa opioid receptor expressed in CHO c... 22439881
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]-U69593 from human kappa opioid receptor transfected in CHO ... 24107104
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO me... 17433695
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U-69593 from human kappa opioid receptors expressed in CHO c... 17276685
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U-69593 from human opioid kappa receptor expressed in CHO ce... 17407276
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 16392810
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Binding affinity against opioid receptor kappa 1 using [3H]-U-69,593 as radiolig... 14695830
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Inhibitory activity against Opioid receptor kappa 1 in chinese Hamster Ovary (CH... 14613319
Kappa-type opioid receptor Ki = 0.079 nM 10.1 Inhibition of [3H]U-69593 binding to Opioid receptor kappa 1 of Chinese hamster ... 15055988
Mu-type opioid receptor Ki = 0.12 nM 9.92 Binding affinity towards Opioid receptor mu 1 in guinea pig brain membranes usin... 11591513
Mu-type opioid receptor Ki = 0.12 nM 9.92 Binding affinity towards Opioid receptor mu 1 by displacing the radioligand [3H]... 10633042

Literature References

PubMed DOI Target Context # Activities
16392810 10.1021/jm050577x Mu-type opioid receptor 6
19634902 10.1021/jm900379p Mu-type opioid receptor 5
16392810 10.1021/jm050577x Kappa-type opioid receptor 5
17407276 10.1021/jm061327z Mu-type opioid receptor 5
17433695 10.1016/j.bmc.2007.03.076 Mu-type opioid receptor 5
19634902 10.1021/jm900379p Kappa-type opioid receptor 5
22439881 10.1021/jm3001086 Mu-type opioid receptor 5
17276685 10.1016/j.bmcl.2007.01.013 Mu-type opioid receptor 5
14613319 10.1021/jm030139v Kappa-type opioid receptor 4
17276685 10.1016/j.bmcl.2007.01.013 Kappa-type opioid receptor 4
17433695 10.1016/j.bmc.2007.03.076 Kappa-type opioid receptor 4
17407276 10.1021/jm061327z Kappa-type opioid receptor 3
24107104 10.1021/jm401290y Rattus norvegicus 3
22439881 10.1021/jm3001086 Kappa-type opioid receptor 3
18674902 10.1016/j.bmcl.2008.07.054 Unchecked 3
15055988 10.1021/jm049978n Kappa-type opioid receptor 3
15055988 10.1021/jm049978n Mu-type opioid receptor 3
19634902 10.1021/jm900379p Unchecked 2
21482470 10.1016/j.bmc.2011.03.052 Unchecked 2
20144870 10.1016/j.bmcl.2010.01.101 Unchecked 2

Data from ChEMBL 36 via Core Engine