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Butorphanol

AlkaPlorer ID: AK007411

Synonym: None

IUPAC Name: (1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol

Structure

SMILES: C1CC[C@]2([C@H]3CC4=C([C@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)O

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InChI: InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1

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InChIKey: IFKLAQQSCNILHL-QHAWAJNXSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 327.46799999999996

TPSA？: 43.7

MolLogP？: 3.3656000000000033

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Kappa opioid receptor pD2 6.49 None 10.1007/s00044-010-9471-6
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 Alpha-2c adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
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 Bile salt export pump IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Bile salt export pump IC50 135000.0 nM 10.1093/toxsci/kfq269
Homo sapiens Bradykinin B2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Canalicular multispecific organic anion transporter 1 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Canalicular multispecific organic anion transporter 2 IC50 133000.0 nM 10.1093/toxsci/kft176
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 Cytochrome P450 1A2 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2C19 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2C9 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2D6 Ratio IC50 2.0 None 10.1021/tx300075j
Homo sapiens Cytochrome P450 3A4 Inhibition nan % 10.1021/tx300075j
Homo sapiens Delta opioid receptor AC50 180.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor Ki 12.0 nM 10.1016/j.bmc.2011.03.052
Homo sapiens Delta opioid receptor Ki 12.0 nM 10.1016/j.bmcl.2008.07.054
Homo sapiens Delta opioid receptor Ki 12.0 nM 10.1016/j.bmcl.2008.10.134
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 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 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 12000.0 nM 10.1038/s41467-023-40064-9
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 41.0 mL.min-1.kg-1 10.1021/jm900403j
Homo sapiens Homo sapiens CL_renal 2.05 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 25.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Kappa opioid receptor Activity nan None 10.1016/j.bmcl.2008.10.134
Homo sapiens Kappa opioid receptor EC50 2.9 nM 10.1016/j.bmcl.2008.10.134
Homo sapiens Kappa opioid receptor Emax 73.0 % 10.1016/j.bmcl.2008.10.134
Homo sapiens Kappa opioid receptor Ki 0.12 nM 10.1016/j.bmc.2011.03.052
Homo sapiens Kappa opioid receptor Ki 0.12 nM 10.1016/j.bmcl.2008.07.054
Homo sapiens Kappa opioid receptor Ki 0.22 nM 10.1016/j.bmcl.2008.10.134
Homo sapiens Liver microsomes Activity nan None 10.1021/tx300075j
Homo sapiens Liver microsomes Stability nan % 10.1021/tx300075j
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 Multidrug resistance-associated protein 4 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Mu opioid receptor AC50 6.1 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor Emax 22.0 % 10.1016/j.bmcl.2008.10.134
Homo sapiens Mu opioid receptor IC50 14.0 nM 10.1016/j.bmcl.2008.10.134
Homo sapiens Mu opioid receptor Imax 54.0 % 10.1016/j.bmcl.2008.10.134
Homo sapiens Mu opioid receptor Ki 0.12 nM 10.1016/j.bmcl.2008.10.134
Homo sapiens Mu opioid receptor Ki 0.22 nM 10.1016/j.bmc.2011.03.052
Homo sapiens Mu opioid receptor Ki 0.22 nM 10.1016/j.bmcl.2008.07.054
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 Peroxisome proliferator-activated receptor gamma AC50 30000.0 nM 10.1038/s41467-023-40064-9
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 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 Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
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
Mus musculus Mus musculus ED50 0.05 mg.kg-1 10.1021/jm00215a012
Mus musculus Mus musculus ED50 0.051 mg.kg-1 10.1021/jm00203a003
Mus musculus Mus musculus ED50 0.27 mg.kg-1 10.1021/jm00203a003
Mus musculus Mus musculus ED50 0.3 umol.kg-1 10.1021/jm00144a015
Mus musculus Mus musculus ED50 0.34 umol.kg-1 10.1021/jm00138a015
Mus musculus Mus musculus ED50 0.34 umol.kg-1 10.1021/jm00138a016
Mus musculus Mus musculus ED50 0.34 umol.kg-1 10.1021/jm00144a029
Mus musculus Mus musculus ED50 0.34 umol.kg-1 10.1021/jm00176a013
Mus musculus Mus musculus ED50 0.34 umol.kg-1 10.1021/jm00186a025
Mus musculus Mus musculus ED50 0.98 mg.kg-1 10.1021/jm00203a003
Mus musculus Mus musculus ED50 0.98 mg.kg-1 10.1021/jm00215a012
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
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 Opioid receptor ED50 2.0 umol.kg-1 10.1021/jm00144a029
Rattus norvegicus Rattus norvegicus ED50 0.04 mg.kg-1 10.1021/jm00203a003
Rattus norvegicus Rattus norvegicus ED50 0.04 mg.kg-1 10.1021/jm00215a012
Rattus norvegicus Rattus norvegicus ED50 0.27 mg.kg-1 10.1021/jm00215a012
Rattus norvegicus Rattus norvegicus ED50 0.43 mg.kg-1 10.1021/jm00203a003
Rattus norvegicus Rattus norvegicus ED50 0.43 mg.kg-1 10.1021/jm00215a012
Rattus norvegicus Rattus norvegicus ED50 2.0 umol.kg-1 10.1021/jm00138a015
Rattus norvegicus Rattus norvegicus ED50 2.0 umol.kg-1 10.1021/jm00138a016
Rattus norvegicus Rattus norvegicus ED50 2.0 umol.kg-1 10.1021/jm00144a015
Rattus norvegicus Rattus norvegicus ED50 2.0 umol.kg-1 10.1021/jm00176a013
Rattus norvegicus Rattus norvegicus ED50 2.0 umol.kg-1 10.1021/jm00186a025
Rattus norvegicus Rattus norvegicus Ratio 0.17 None 10.1021/jm00176a013
Rattus norvegicus Rattus norvegicus Ratio 0.17 None 10.1021/jm00186a025
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 CL 41.0 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET Fu 0.18 None 10.1021/jm030408h
None ADMET MRT 5.3 hr 10.1124/dmd.108.020479
None ADMET T1/2 4.8 hr 10.1124/dmd.108.020479
None ADMET Vdss 8.8 L.kg-1 10.1021/jm030408h
None ADMET Vdss 12.0 L.kg-1 10.1124/dmd.108.020479
None Hepatotoxicity Alkaline Phosphatase Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity Alkaline Phosphatase Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Alkaline Phosphatase Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Active 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Marginal 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Score nan None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
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 0.0 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 0.0 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 Hepatotoxicity LDH Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity LDH Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity LDH Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None NON-PROTEIN TARGET Fu 0.17 None 10.1124/dmd.108.020479
None No relevant target pKa 8.19 None 10.1007/s11095-013-1232-z
None No relevant target pKa 8.19 None 10.1021/jm030408h
None No relevant target Solubility 500000.0 nM 10.1016/j.bmcl.2010.10.068
None Phospholipidosis Phospholipidosis nan None 10.1080/15376510701857262
None Unchecked Ratio Ki 0.55 None 10.1016/j.bmcl.2008.10.134
None Unchecked Ratio Ki 1.0 None 10.1016/j.bmcl.2008.07.054
None Unchecked Ratio Ki 2.0 None 10.1016/j.bmc.2011.03.052
None Unchecked Ratio Ki 2.0 None 10.1016/j.bmcl.2008.07.054
None Unchecked Ratio Ki 50.0 None 10.1016/j.bmcl.2008.10.134
None Unchecked Ratio Ki 100.0 None 10.1016/j.bmc.2011.03.052
None Unchecked Ratio Ki 100.0 None 10.1016/j.bmcl.2008.07.054

Metabolism Information