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Compound Detail

CHEMBL1400

O-DESMETHYL TRAMADOL
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CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1400
Name O-DESMETHYL TRAMADOL
Phase Preclinical
Structure Type MOL
InChI Key UWJUQVWARXYRCG-HIFRSBDPSA-N
6
Targets
14
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

249.3
MW (Da)
2.33
ALogP
3
HBA
2
HBD
43.7
PSA (Ų)
0.86
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H23NO2
MW 249.35
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 0.90

Activity Summary

Ki 7 meas. best 8.07
EC50 4 meas. best 6.92
IC50 3 meas. best 7.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 8.07 7.9733 8.6 3
Mu-type opioid receptor
CHEMBL270
 Ki 7.89 7.89 13.0 1
Mu-type opioid receptor
CHEMBL2858
 Ki 7.89 7.89 13.0 1
Mu-type opioid receptor
CHEMBL233
 IC50 7.33 7.33 47.0 2
Mu-type opioid receptor
CHEMBL233
 EC50 6.92 6.7167 120.0 3
Mu-type opioid receptor
CHEMBL270
 EC50 6.61 6.61 244.7 1
Kappa-type opioid receptor
CHEMBL237
 Ki 6.35 6.35 450.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 5.54 5.54 2900.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 5.34 5.34 4600.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 47.0 hr Homo sapiens
T1/2 26.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 8.6 nM 8.07 Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells 19027293
Mu-type opioid receptor Ki = 11.0 nM 7.96 Displacement of [3H]naloxone from human MOR expressed in CHO-K1 cell membranes a... 27096047
Mu-type opioid receptor Ki = 13.0 nM 7.89 Displacement of [3H]DAMGO from human MOR expressed in CHO cell membranes after 6... 27096047
Mu-type opioid receptor Ki = 13.0 nM 7.89 Displacement of [3H]-DAMGO from rat mu opioid receptor expressed in CHO cells in... 31982651
Mu-type opioid receptor Ki = 13.0 nM 7.89 Displacement of [3H] DAMGO from mouse MOR expressed in CHO cell membrane incubat... 34152138
Mu-type opioid receptor IC50 = 47.0 nM 7.33 Inhibition of mu opioid receptor 16257206
Mu-type opioid receptor IC50 = 47.0 nM 7.33 Binding affinity to mu opioid receptor 18242987
Mu-type opioid receptor EC50 = 120.0 nM 6.92 Agonist activity at human mu opioid receptor expressed in CHO cells assessed as ... 24900459
Mu-type opioid receptor EC50 = 240.0 nM 6.62 Agonist activity at human MOR expressed in CHO cell membranes after 60 mins by [... 27096047
Mu-type opioid receptor EC50 = 244.7 nM 6.61 Agonist activity at rat mu opioid receptor expressed in CHO cells incubated for ... 31982651
Mu-type opioid receptor EC50 = 244.7 nM 6.61 Agonist activity at MOR (unknown origin) expressed in CHO cell membranes assesse... 34152138
Kappa-type opioid receptor Ki = 450.0 nM 6.35 Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cel... 19027293
Delta-type opioid receptor Ki = 2900.0 nM 5.54 Displacement of [3H]Naltrindole form human delta opioid receptor expressed in CH... 19027293
Sodium-dependent serotonin transporter IC50 = 4600.0 nM 5.34 Inhibition of reuptake of 5HT 16257206

Literature References

PubMed DOI Target Context # Activities
27096047 10.1021/acsmedchemlett.5b00423 Mu-type opioid receptor 4
31982651 10.1016/j.ejmech.2020.112070 Kappa-type opioid receptor 3
31982651 10.1016/j.ejmech.2020.112070 Delta-type opioid receptor 3
31982651 10.1016/j.ejmech.2020.112070 Mu-type opioid receptor 3
34152138 10.1021/acs.jmedchem.1c00722 Mu-type opioid receptor 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
19027293 10.1016/j.bmcl.2008.10.134 Unchecked 2
19027293 10.1016/j.bmcl.2008.10.134 Delta-type opioid receptor 1
34152138 10.1021/acs.jmedchem.1c00722 Kappa-type opioid receptor 1
24900459 10.1021/ml200268w Mu-type opioid receptor 1
19027293 10.1016/j.bmcl.2008.10.134 Mu-type opioid receptor 1
16257206 10.1016/j.bmcl.2005.10.024 Mu-type opioid receptor 1
19027293 10.1016/j.bmcl.2008.10.134 Kappa-type opioid receptor 1
18242987 10.1016/j.bmcl.2008.01.051 Rattus norvegicus 1
18242987 10.1016/j.bmcl.2008.01.051 Sodium-dependent noradrenaline transporter 1
18242987 10.1016/j.bmcl.2008.01.051 Sodium-dependent serotonin transporter 1
18242987 10.1016/j.bmcl.2008.01.051 Mu-type opioid receptor 1
16257206 10.1016/j.bmcl.2005.10.024 Hepatocyte 1
16257206 10.1016/j.bmcl.2005.10.024 Liver microsomes 1
16257206 10.1016/j.bmcl.2005.10.024 Sodium-dependent noradrenaline transporter 1

Data from ChEMBL 36 via Core Engine