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Compound Detail

CHEMBL401093

OXYMORPHINDOLE
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CN1CC[C@]23c4c5ccc(O)c4O[C@H]2c2[nH]c4ccccc4c2C[C@@]3(O)[C@H]1C5
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL401093
Name OXYMORPHINDOLE
Phase Preclinical
Structure Type MOL
InChI Key YQNZUKAKYJMEFE-LMDOGRNLSA-N
11
Targets
26
Activities
1
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

374.4
MW (Da)
2.79
ALogP
4
HBA
3
HBD
68.7
PSA (Ų)
0.57
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H22N2O3
MW 374.44
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness 1.62

Activity Summary

Ki 26 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Delta-type opioid receptor
CHEMBL236
 Ki 9.15 9.078 0.7 5
Delta-type opioid receptor
CHEMBL269
 Ki 9.1 8.9 0.8 2
Delta-type opioid receptor
CHEMBL3222
 Ki 9.1 9.1 0.8 2
Mu-type opioid receptor
CHEMBL270
 Ki 7.18 7.0433 66.0 3
Kappa-type opioid receptor
CHEMBL4329
 Ki 7.11 7.11 77.0 1
Mu-type opioid receptor
CHEMBL233
 Ki 6.98 6.71 105.0 2
Kappa-type opioid receptor
CHEMBL237
 Ki 6.4 6.345 396.0 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 6.4 5.6125 395.0 4
Mu-type opioid receptor
CHEMBL4354
 Ki 6.33 6.33 468.0 3
Mu-type opioid receptor
CHEMBL2858
 Ki 6.18 6.18 661.0 1
Kappa-type opioid receptor
CHEMBL3614
 Ki 5.66 5.66 2170.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 5.0 nM -
Ke 111.0 nM Cavia porcellus
Ke 167.0 nM Cavia porcellus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Delta-type opioid receptor Ki = 0.7 nM 9.15 Binding affinity was measured by the displacement of [3H]- DADLE in guinea pig b... 2160538
Delta-type opioid receptor Ki = 0.7 nM 9.15 The compound was evaluated for binding affinity against Opioid receptor delta 1 ... 1333013
Delta-type opioid receptor Ki = 0.7 nM 9.15 Binding affinity was measured by the displacement of [3H]- DADLE in guinea pig b... 2160538
Delta-type opioid receptor Ki = 0.8 nM 9.1 Binding affinity against Opioid receptor delta 1 using [3H][D-Ala2, D-Leu5]-enke... 9379438
Delta-type opioid receptor Ki = 0.8 nM 9.1 Displacement of [3H]DADLE at delta-opioid receptor 11311071
Delta-type opioid receptor Ki = 0.8 nM 9.1 Binding affinity to delta opioid receptor in rat brain membrane 18403056
Delta-type opioid receptor Ki = 0.9 nM 9.05 Displacement of [3H]p-Cl-DPDPE from delta opioid receptor 17826993
Delta-type opioid receptor Ki = 1.28 nM 8.89 Displacement of [3H]C1-DPDPE from human recombinant Opioid receptor delta 1 on C... 12672258
Delta-type opioid receptor Ki = 2.0 nM 8.7 Opioid receptor delta 1 binding affinity was determined by inhibition of binding... 12431065
Mu-type opioid receptor Ki = 66.0 nM 7.18 Displacement of [3H]DAMGO at mu-opioid receptor 11311071
Mu-type opioid receptor Ki = 66.0 nM 7.18 Binding affinity to mu opioid receptor in rat brain membrane 18403056
Kappa-type opioid receptor Ki = 77.0 nM 7.11 Binding affinity against Opioid receptor kappa 1 using [3H]-U-69,593 as radiolig... 9379438
Mu-type opioid receptor Ki = 105.0 nM 6.98 Displacement of [3H]DAMGO from mu opioid receptor 17826993
Mu-type opioid receptor Ki = 171.0 nM 6.77 Binding affinity at mu opioid receptor 1 in rat brain membrane by [3H]DAMGO disp... 12431065
Mu-type opioid receptor Ki = 363.0 nM 6.44 Displacement of [3H]DAMGO from human recombinant Opioid receptor mu 1 on CHO cel... 12672258
Kappa-type opioid receptor Ki = 396.0 nM 6.4 Displacement of [3H]U-69593 from human recombinant Opioid receptor kappa 1 on CH... 12672258
Kappa-type opioid receptor Ki = 395.0 nM 6.4 Binding affinity at kappa opioid receptor 1 in guinea pig brain by [3H]U-69593 d... 12431065
Mu-type opioid receptor Ki = 468.0 nM 6.33 Binding affinity was measured by the displacement of [3H]- DAMGO in guinea pig b... 2160538
Mu-type opioid receptor Ki = 468.0 nM 6.33 Binding affinity was measured by the displacement of [3H]- DAMGO in guinea pig b... 2160538
Mu-type opioid receptor Ki = 468.0 nM 6.33 The compound was evaluated for binding affinity against opioid receptor mu in gu... 1333013

Literature References

PubMed DOI Target Context # Activities
2160538 10.1021/jm00168a028 Mu-type opioid receptor 5
2160538 10.1021/jm00168a028 Kappa-type opioid receptor 5
2160538 10.1021/jm00168a028 Delta-type opioid receptor 5
17826993 10.1016/j.bmcl.2007.07.098 Mus musculus 4
1333013 10.1021/jm00101a009 Mus musculus 4
1333013 10.1021/jm00101a009 Cavia porcellus 3
18403056 10.1016/j.ejmech.2008.02.011 Unchecked 2
1333013 10.1021/jm00101a009 Mu-type opioid receptor 2
1333013 10.1021/jm00101a009 Delta-type opioid receptor 2
17367120 10.1021/jm0612463 Delta-type opioid receptor 2
12672258 10.1021/jm021073r Mu-type opioid receptor 1
12672258 10.1021/jm021073r Opioid receptors; delta & kappa 1
12672258 10.1021/jm021073r Opioid receptors; mu & delta 1
12431065 10.1021/jm020940p Delta-type opioid receptor 1
12431065 10.1021/jm020940p Mu-type opioid receptor 1
12431065 10.1021/jm020940p Kappa-type opioid receptor 1
12431065 10.1021/jm020940p Opioid receptors; mu & delta 1
12672258 10.1021/jm021073r Kappa-type opioid receptor 1
1333013 10.1021/jm00101a009 Kappa-type opioid receptor 1
9379438 10.1021/jm9608218 Delta-type opioid receptor 1

Data from ChEMBL 36 via Core Engine