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name Structure Reference Source Properties Activities Metabolism

Oxycodone

AlkaPlorer ID: AK015941

Synonym: None

IUPAC Name: (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

Structure

SMILES: COC1=C2O[C@H]3C(=O)CC[C@@]4(O)[C@H]5CC(=C2[C@@]34CCN5C)C=C1

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InChI: InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1

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InChIKey: BRUQQQPBMZOVGD-XFKAJCMBSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Papaver somniferum Papaver Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 315.369

TPSA？: 59.00000000000001

MolLogP？: 1.0481999999999996

Number of H-Donors: 1

Number of H-Acceptors: 5

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Kappa opioid receptor Ki 325.0 nM 10.1016/j.ejmech.2019.05.037
Cavia porcellus Kappa opioid receptor Ki 10000.0 nM 10.1016/j.bmc.2010.05.071
Electrophorus electricus Acetylcholinesterase IC50 76200.0 nM 10.1016/j.bmc.2010.05.071
Electrophorus electricus Acetylcholinesterase Inhibition 80.0 % 10.1016/j.bmc.2010.05.071
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Aryl hydrocarbon receptor Activity nan None 10.1124/dmd.112.050401
Homo sapiens Beta-1 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bradykinin B2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin A receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin B receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor EC50 4000.0 nM 10.1016/j.bmcl.2013.06.084
Homo sapiens Delta opioid receptor Inhibition 93.0 % 10.1016/j.bmcl.2013.06.084
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endothelin receptor ET-A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Equilibrative nucleoside transporter 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ghrelin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG IC50 10000.0 nM 10.1021/acs.jmedchem.0c01127
Homo sapiens HERG Inhibition 50.0 % 10.1021/acs.jmedchem.0c01127
Homo sapiens Histamine H1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Homo sapiens CL 6.1 mL.min-1.kg-1 10.1021/jm900403j
Homo sapiens Homo sapiens CL_renal 1.1 mL.min-1.kg-1 10.1021/jm900403j
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 0.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Kappa opioid receptor AC50 2000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Kappa opioid receptor EC50 16000.0 nM 10.1016/j.bmcl.2013.06.084
Homo sapiens Kappa opioid receptor Inhibition 47.0 % 10.1016/j.bmcl.2013.06.084
Homo sapiens Melanocortin receptor 3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 230.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 29000.1 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor EC50 17.0 nM 10.1021/acs.jmedchem.0c01127
Homo sapiens Mu opioid receptor EC50 17.0 nM 10.1021/acs.jmedchem.1c00417
Homo sapiens Mu opioid receptor EC50 17.0 nM 10.1021/acs.jmedchem.9b01256
Homo sapiens Mu opioid receptor EC50 478.0 nM None
Homo sapiens Mu opioid receptor EC50 500.0 nM 10.1016/j.bmcl.2013.06.084
Homo sapiens Mu opioid receptor Emax 100.0 % 10.1021/acs.jmedchem.0c01127
Homo sapiens Mu opioid receptor Emax 100.0 % 10.1021/acs.jmedchem.1c00417
Homo sapiens Mu opioid receptor Emax 100.0 % 10.1021/acs.jmedchem.9b01256
Homo sapiens Mu opioid receptor Inhibition 93.0 % 10.1016/j.bmcl.2013.06.084
Homo sapiens Mu opioid receptor Ki 12.0 nM 10.1021/acs.jmedchem.0c01127
Homo sapiens Mu opioid receptor Ki 12.0 nM 10.1021/acs.jmedchem.1c00417
Homo sapiens Mu opioid receptor Ki 12.0 nM 10.1021/acs.jmedchem.9b01256
Homo sapiens Mu opioid receptor Ki 133.48 nM None
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Nuclear receptor subfamily 1 group I member 3 Activity nan None 10.1124/dmd.112.050401
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pregnane X receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pregnane X receptor Activity nan None 10.1124/dmd.112.050401
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2c (5-HT2c) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 3a (5-HT3a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Sigma opioid receptor Inhibition 50.0 % 10.1021/acs.jmedchem.0c01127
Homo sapiens Sigma opioid receptor Inhibition 50.0 % 10.1021/acs.jmedchem.9b01256
Homo sapiens Sigma opioid receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01127
Homo sapiens Sigma opioid receptor Ki 10000.0 nM 10.1021/acs.jmedchem.1c00417
Homo sapiens Sigma opioid receptor Ki 10000.0 nM 10.1021/acs.jmedchem.9b01256
Homo sapiens Solute carrier family 22 member 1 FC 0.8 None 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 FC 0.9 None 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 IC50 2003780.0 nM 10.1021/acs.jmedchem.9b01301
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens UDP-glucuronosyltransferase 1A4 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B15 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens Vasopressin V1a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Whole blood Retention_time 2.67 min 10.1007/s00044-012-9977-1
Mus musculus Constitutive androstane receptor Activity nan None 10.1124/dmd.112.050401
Mus musculus Kappa opioid receptor EC50 16000.0 nM 10.1016/j.bmcl.2013.06.084
Mus musculus Kappa opioid receptor Inhibition 59.0 % 10.1016/j.bmcl.2013.06.084
Mus musculus Mu opioid receptor EC50 160.0 nM 10.1016/j.bmcl.2013.06.084
Mus musculus Mu opioid receptor Inhibition 97.0 % 10.1016/j.bmcl.2013.06.084
Mus musculus Mus musculus Activity 0.9 % 10.1016/j.bmc.2015.03.049
Mus musculus Mus musculus Activity 3.9 % 10.1016/j.bmc.2015.03.049
Mus musculus Mus musculus Activity 41.0 % 10.1021/acs.jmedchem.1c00417
Mus musculus Mus musculus Activity 77.0 % 10.1021/acs.jmedchem.1c00417
Mus musculus Mus musculus Activity 89.0 % 10.1021/acs.jmedchem.1c00417
Mus musculus Mus musculus Activity nan None 10.1021/acs.jmedchem.9b01256
Mus musculus Mus musculus ED50 0.38 mg.kg-1 10.1021/jm0580205
Mus musculus Mus musculus ED50 0.94 mg.kg-1 10.1021/jm0580205
Mus musculus Mus musculus ED50 1.3 mg.kg-1 10.1021/jm00225a021
Mus musculus Mus musculus ED50 1.37 mg.kg-1 10.1021/jm0580205
Mus musculus Mus musculus ED50 1.5 umol.kg-1 10.1021/jm00144a015
Mus musculus Mus musculus ED50 4.0 mg.kg-1 10.1021/acs.jmedchem.1c00417
Mus musculus Mus musculus ED50 4.3 mg.kg-1 10.1021/acs.jmedchem.9b01256
Mus musculus Mus musculus Inhibition 51.0 % 10.1021/acs.jmedchem.0c01127
Mus musculus Mus musculus MPE 52.9 % 10.1016/j.bmc.2015.03.049
Mus musculus Mus musculus MPE 63.3 % 10.1016/j.bmc.2015.03.049
Mus musculus Mus musculus MPE 66.9 % 10.1016/j.bmc.2015.03.049
Mus musculus Mus musculus UI 1.5 None 10.1016/j.bmc.2015.03.049
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Brain Fu 0.66 None 10.1124/dmd.110.035998
Rattus norvegicus Brain Kp 2.78 None 10.1124/dmd.110.035998
Rattus norvegicus Brain Vd 4.2 L.kg-1 10.1124/dmd.110.035998
Rattus norvegicus Brain Vdu 4.2 ml 10.1021/jm901036q
Rattus norvegicus Cannabinoid receptor Ki 10000.0 nM 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Delta opioid receptor Ki 487.0 nM 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Delta opioid receptor Ki 1087.0 nM 10.1021/jm0580205
Rattus norvegicus Delta opioid receptor Ki 10000.0 nM 10.1016/j.bmc.2010.05.071
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Kappa opioid receptor Ki 2658.0 nM 10.1021/jm0580205
Rattus norvegicus Mu opioid receptor EC50 25.0 nM 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Mu opioid receptor Emax 137.0 % 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Mu opioid receptor Ki 8.9 nM 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Mu opioid receptor Ki 43.6 nM 10.1021/jm0580205
Rattus norvegicus Mu opioid receptor Ki 10000.0 nM 10.1016/j.bmc.2010.05.071
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 Activity nan None 10.1124/dmd.112.050401
Rattus norvegicus Opioid receptors; mu & delta Selectivity ratio 25.0 None 10.1021/jm0580205
Rattus norvegicus Plasma Cp(f) 0.33 uM 10.1021/jm901036q
Rattus norvegicus Plasma Fu 0.87 None 10.1021/jm901036q
Rattus norvegicus Plasma K(p,uu,CSF) 0.65 None 10.1021/jm901036q
Rattus norvegicus Rattus norvegicus Activity 40.0 g 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Rattus norvegicus Activity 43.0 g 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Rattus norvegicus Activity nan None 10.1016/j.ejmech.2019.05.037
Rattus norvegicus Rattus norvegicus ED50 2.9 umol.kg-1 10.1021/jm00144a015
Rattus norvegicus Rattus norvegicus K(p,uu,brain) 3.0 None 10.1124/dmd.110.036434
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None ADMET Activity nan None 10.1021/acs.jmedchem.0c01127
None ADMET Activity nan None 10.1021/acs.jmedchem.1c00417
None ADMET Activity nan None 10.1124/dmd.112.050401
None ADMET BPR 3.77 None 10.1021/jm901036q
None ADMET CL 6.1 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET Cmax 50.0 nM 10.1021/acs.jmedchem.9b01301
None ADMET fCmax 0.03 uM 10.1021/acs.jmedchem.9b01301
None ADMET fCmax 0.54 uM 10.1021/acs.jmedchem.9b01301
None ADMET fCmax 1.06 uM 10.1021/acs.jmedchem.9b01301
None ADMET Fu 0.55 None 10.1021/jm030408h
None ADMET K(p,uu,brain) 1.03 None 10.1021/jm901036q
None ADMET log10(%HIA +10) 1.845 None 10.1016/j.ejmech.2010.11.005
None ADMET MRT 6.8 hr 10.1124/dmd.108.020479
None ADMET T1/2 5.5 hr 10.1124/dmd.108.020479
None ADMET Vdss 2.3 L.kg-1 10.1021/jm030408h
None ADMET Vdss 2.5 L.kg-1 10.1124/dmd.108.020479
None Hepatotoxicity HepSE_bilirubinemia 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholecystitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholelithiasis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cirrhosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_Combined Scores 1.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_elevated liver function tests 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic failure 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic necrosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatomegaly 1.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_jaundice 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver disease 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver fatty 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver function tests abnormal 0.0 None 10.1371/journal.pcbi.1002310
None NON-PROTEIN TARGET Fu 0.55 None 10.1124/dmd.108.020479
None No relevant target Peff 17.9 ucm/s 10.1021/acs.jmedchem.9b01301
None No relevant target pKa 8.53 None 10.1007/s11095-013-1232-z
None No relevant target pKa 8.53 None 10.1021/jm030408h
None No relevant target pKa 9.1 None 10.1124/dmd.110.035998
None Unchecked EC50 51.0 nM 10.1016/j.ejmech.2019.05.037
None Unchecked Emax 135.0 % 10.1016/j.ejmech.2019.05.037
None Unchecked Ratio 1e-05 None 10.1021/acs.jmedchem.9b01301
None Unchecked Ratio 0.0003 None 10.1021/acs.jmedchem.9b01301
None Unchecked Ratio 0.001 None 10.1021/acs.jmedchem.9b01301
None Unchecked Ratio EC50 4.0 None 10.1016/j.bmcl.2013.06.084
None Unchecked Ratio EC50 32.0 None 10.1016/j.bmcl.2013.06.084
None Unchecked Ratio Ki 37.0 None 10.1016/j.ejmech.2019.05.037
None Unchecked Ratio Ki 55.0 None 10.1016/j.ejmech.2019.05.037
None Unchecked Selectivity ratio 1.0 None 10.1016/j.bmc.2010.05.071
None Unchecked Selectivity ratio 61.0 None 10.1021/jm0580205

Metabolism Information