Navigation

name Structure Reference Source Properties Activities Metabolism

Codeine

AlkaPlorer ID: AK001141

Synonym: None

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

Structure

SMILES: COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@]45CCN3C

copy

InChI: InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1

copy

InChIKey: OROGSEYTTFOCAN-DNJOTXNNSA-N

copy

Properties Information

Molecule Weight: 299.37000000000006

TPSA？: 41.93

MolLogP？: 1.5011

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Cavia porcellus Activity nan None 10.1007/s00044-011-9641-1
Cavia porcellus Cavia porcellus Activity nan None 10.1016/j.bmcl.2022.129067
Cavia porcellus Cavia porcellus Activity nan None 10.1021/jm9008218
Cavia porcellus Cavia porcellus ED50 6.7 mg.kg-1 10.1016/j.bmcl.2009.03.057
Cavia porcellus Cavia porcellus ED50 6.8 mg.kg-1 10.1016/j.bmcl.2009.03.031
Cavia porcellus Cavia porcellus ED50 6.8 mg.kg-1 10.1021/jm9008218
Cavia porcellus Cavia porcellus ED50 38.5 mg.kg-1 10.1021/jm00212a003
Cavia porcellus Cavia porcellus ED50 nan None 10.1016/j.bmcl.2009.03.031
Cavia porcellus Cavia porcellus Inhibition 80.0 % 10.1021/jm00212a003
Cavia porcellus Cavia porcellus Inhibition nan % 10.1007/s00044-011-9641-1
Cercopithecidae Monkey Antagonist potency nan None 10.1021/jm00098a001
Cercopithecidae Monkey ED50 7.5 mg.kg-1 10.1021/jm00098a001
Cercopithecidae Monkey PDC nan None 10.1021/jm00098a001
Cercopithecidae Monkey Physical dependence capacity nan None 10.1021/jm00177a001
Cryptosporidium parvum Cryptosporidium parvum IC50 nan None 10.1016/j.bmc.2010.01.068
Entamoeba histolytica Entamoeba histolytica IC50 nan None 10.1016/j.bmc.2010.01.068
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 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-1 adrenergic receptor AC50 900.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-3 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bradykinin B1 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 10000.0 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 Corticotropin releasing factor receptor 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Corticotropin releasing factor receptor 2 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 2D6 Activity nan None None
Homo sapiens Cytochrome P450 2D6 IC50 104000.0 nM 10.1021/jm0209578
Homo sapiens Delta opioid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor IC50 9300.0 nM 10.1021/jm020164l
Homo sapiens Delta opioid receptor Ki 52207.0 nM 10.1021/jm701457j
Homo sapiens Dopamine D1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D4 receptor AC50 10000.0 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 Endothelin receptor ET-B 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 Estrogen receptor beta AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens GABA-B receptor 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Gastric inhibitory polypeptide receptor 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 Glucagon 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 301995.17 nM 10.1016/j.bmcl.2005.03.080
Homo sapiens Histamine H1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Homo sapiens CL 15.0 mL.min-1.kg-1 10.1021/jm900403j
Homo sapiens Homo sapiens CL_renal 1.7 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 Homo sapiens F 55.0 % 10.1016/j.bmc.2007.08.060
Homo sapiens Homo sapiens Vdss 3.5 L.kg-1 10.1016/j.ejmech.2009.06.004
Homo sapiens Kappa opioid receptor AC50 4941.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Kappa opioid receptor IC50 15000.0 nM 10.1021/jm020164l
Homo sapiens Kappa opioid receptor Ki 25411.0 nM 10.1021/jm701457j
Homo sapiens Melanocortin receptor 3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 4 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 540.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 1100.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor EC50 6100.0 nM 10.1074/jbc.m703272200
Homo sapiens Mu opioid receptor Emax 81.3 % 10.1074/jbc.m703272200
Homo sapiens Mu opioid receptor IC50 105.0 nM 10.1021/jm020164l
Homo sapiens Mu opioid receptor Ki 727.0 nM 10.1021/jm701457j
Homo sapiens Mu opioid receptor Ki 6300.0 nM 10.1074/jbc.m703272200
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 10000.0 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 Muscarinic acetylcholine receptor M5 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neurokinin 1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 10000.0 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 Neuropeptide Y receptor type 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neurotensin receptor 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 Opioid receptors; mu & delta Ratio 89.0 None 10.1021/jm020164l
Homo sapiens P-glycoprotein 1 Activity nan None 10.1021/jm701457j
Homo sapiens Phosphodiesterase 3A AC50 3000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 7200.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Plasma K(p,uu,CSF) 0.79 None 10.1021/jm901036q
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 6 (5-HT6) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 7 (5-HT7) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Skin log Kp -7.68 None 10.1016/j.bmc.2007.07.050
Homo sapiens Sodium channel alpha subunits; brain (Types I, II, III) Inhibition 5.7 % 10.1021/jm00381a019
Homo sapiens Sodium channel protein type V alpha subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier family 22 member 1 FC 0.7 None 10.1021/acs.jmedchem.9b01301
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 1.0 None 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 IC50 235500.0 nM 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 Inhibition 39.1 % 10.1021/jm8003152
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 1-10 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-3 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-8 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
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 UDP-glucuronosyltransferase 2B4 Activity nan None None
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 1.8 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 54.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 80.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 114.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Km 400000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Km 1800000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Vmax 9.0 pmol/min/mg protein 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Vmax 74.0 pmol/min/mg protein 10.1016/j.pharmthera.2004.10.013
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 2.5 min 10.1007/s00044-012-9977-1
Leishmania amazonensis Leishmania amazonensis IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania donovani Leishmania donovani IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania infantum Leishmania infantum IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania major Leishmania major IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania mexicana Leishmania mexicana IC50 nan None 10.1016/j.bmc.2010.01.068
Mus musculus Monoamine oxidase A Activity nan None 10.1021/jm800656v
Mus musculus Monoamine oxidase B Activity nan None 10.1021/jm800656v
Mus musculus Mus musculus Activity 5.0 None 10.1021/np0497649
Mus musculus Mus musculus Activity 17.0 None 10.1016/j.ejmech.2018.12.066
Mus musculus Mus musculus AD50 nan None 10.1021/jm00370a019
Mus musculus Mus musculus Behavior nan None 10.1021/jm00056a010
Mus musculus Mus musculus ED50 1.4 mg.kg-1 10.1021/jm00370a019
Mus musculus Mus musculus ED50 2.3 mg.kg-1 10.1021/jm00352a037
Mus musculus Mus musculus ED50 4.5 mg.kg-1 10.1021/jm00205a007
Mus musculus Mus musculus ED50 4.5 mg.kg-1 10.1021/jm00218a021
Mus musculus Mus musculus ED50 4.5 mg.kg-1 10.1021/jm00221a027
Mus musculus Mus musculus ED50 5.8 mg.kg-1 10.1021/jm00190a020
Mus musculus Mus musculus ED50 6.8 mg.kg-1 10.1021/jm00370a019
Mus musculus Mus musculus ED50 7.5 mg.kg-1 10.1021/jm00177a001
Mus musculus Mus musculus ED50 7.5 mg.kg-1 10.1021/jm00200a021
Mus musculus Mus musculus ED50 7.5 mg.kg-1 10.1021/jm00205a007
Mus musculus Mus musculus ED50 7.5 mg.kg-1 10.1021/jm00218a021
Mus musculus Mus musculus ED50 7.5 mg.kg-1 10.1021/jm00221a027
Mus musculus Mus musculus ED50 9.7 mg.kg-1 10.1021/jm00056a010
Mus musculus Mus musculus ED50 10.2 umol.kg-1 10.1021/jm00186a025
Mus musculus Mus musculus ED50 10.3 mg.kg-1 10.1021/jm00355a012
Mus musculus Mus musculus ED50 10.3 umol.kg-1 10.1021/jm00138a015
Mus musculus Mus musculus ED50 10.3 umol.kg-1 10.1021/jm00138a016
Mus musculus Mus musculus ED50 10.3 umol.kg-1 10.1021/jm00144a015
Mus musculus Mus musculus ED50 10.3 umol.kg-1 10.1021/jm00176a013
Mus musculus Mus musculus ED50 10.3 umol.kg-1 10.1021/jm00361a019
Mus musculus Mus musculus ED50 14.5 mg.kg-1 10.1021/jm00370a019
Mus musculus Mus musculus ED50 21.4 mg.kg-1 10.1021/jm00225a021
Mus musculus Mus musculus ED50 38.97 mg.kg-1 10.1021/jm00352a037
Mus musculus Mus musculus Mortality 40.0 % 10.1021/jm00056a010
Mus musculus Opioid receptor IC50 10000.0 nM 10.1021/jm00352a037
Plasmodium falciparum Plasmodium falciparum IC50 nan None 10.1016/j.bmc.2010.01.068
Pneumocystis carinii Pneumocystis carinii IC50 nan None 10.1016/j.bmc.2010.01.068
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Brain Fu 0.62 None 10.1124/dmd.110.035998
Rattus norvegicus Brain Kp 1.99 None 10.1124/dmd.110.035998
Rattus norvegicus Brain Vd 3.2 L.kg-1 10.1124/dmd.110.035998
Rattus norvegicus Brain Vdu 3.2 ml 10.1021/jm901036q
Rattus norvegicus Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cytochrome P450 2D1 IC50 1320000.0 nM 10.1021/jm0209578
Rattus norvegicus Cytochrome P450 2D18 IC50 2216000.0 nM 10.1021/jm0209578
Rattus norvegicus Cytochrome P450 2D2 IC50 238000.0 nM 10.1021/jm0209578
Rattus norvegicus Cytochrome P450 2D3 IC50 4089000.0 nM 10.1021/jm0209578
Rattus norvegicus GABA receptor alpha-1 subunit AC50 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Liver microsome CL 8.35 mL.min-1.g-1 10.1016/j.bmc.2013.09.062
Rattus norvegicus Liver microsome CL 11.95 mL.min-1.g-1 10.1016/j.bmc.2013.09.062
Rattus norvegicus Liver microsome CL 18.65 mL.min-1.g-1 10.1016/j.bmc.2013.09.062
Rattus norvegicus Liver microsome CL 31.11 mL.min-1.g-1 10.1016/j.bmc.2013.09.062
Rattus norvegicus Liver microsome CL 47.97 mL.min-1.g-1 10.1016/j.bmc.2013.09.062
Rattus norvegicus Mu opioid receptor Kp 11.4 None 10.1021/jm00398a007
Rattus norvegicus Mu opioid receptor KT 13.3 None 10.1021/jm00398a007
Rattus norvegicus Plasma Cp(f) 0.21 uM 10.1021/jm901036q
Rattus norvegicus Plasma Fu 0.95 None 10.1021/jm901036q
Rattus norvegicus Plasma K(p,uu,CSF) 0.54 None 10.1021/jm901036q
Rattus norvegicus Plasma logFu 0.93 None 10.1016/j.ejmech.2009.06.004
Rattus norvegicus Rattus norvegicus Activity 25.0 mm 10.1021/jm00207a023
Rattus norvegicus Rattus norvegicus Activity 40.0 mm 10.1021/jm00207a023
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/jm9008218
Rattus norvegicus Rattus norvegicus DOSE 50.0 mg.kg-1 10.1021/jm00355a012
Rattus norvegicus Rattus norvegicus ED50 5.7 mg.kg-1 10.1021/jm00355a012
Rattus norvegicus Rattus norvegicus ED50 75.0 umol.kg-1 10.1021/jm00138a015
Rattus norvegicus Rattus norvegicus ED50 75.0 umol.kg-1 10.1021/jm00144a015
Rattus norvegicus Rattus norvegicus ED50 75.0 umol.kg-1 10.1021/jm00176a013
Rattus norvegicus Rattus norvegicus ED50 75.0 umol.kg-1 10.1021/jm00186a025
Rattus norvegicus Rattus norvegicus ED50 75.1 umol.kg-1 10.1021/jm00138a016
Rattus norvegicus Rattus norvegicus ED50 nan None 10.1016/j.bmcl.2009.03.031
Rattus norvegicus Rattus norvegicus IC50 2600.0 nM 10.1021/jm00371a012
Rattus norvegicus Rattus norvegicus IC50 22000.0 nM 10.1021/jm00371a012
Rattus norvegicus Rattus norvegicus Inhibition 20.0 % 10.1021/jm00056a010
Rattus norvegicus Rattus norvegicus Inhibition 70.0 % 10.1021/jm400143z
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Voltage-gated N-type calcium channel alpha-1B subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Toxoplasma gondii Toxoplasma gondii IC50 nan None 10.1016/j.bmc.2010.01.068
Trichomonas vaginalis Trichomonas vaginalis IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei Trypanosoma brucei IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma cruzi Trypanosoma cruzi IC50 nan None 10.1016/j.bmc.2010.01.068
None ADMET BPR 2.7 None 10.1021/jm901036q
None ADMET CL 15.0 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET delta logD -0.8 None 10.1021/jm0000564
None ADMET F 79.0 % 10.1021/jm0000564
None ADMET Fu 0.93 None 10.1021/jm030408h
None ADMET K(p,uu,brain) 0.89 None 10.1021/jm901036q
None ADMET log10(%HIA +10) 2.021 None 10.1016/j.ejmech.2010.11.005
None ADMET MRT 3.9 hr 10.1124/dmd.108.020479
None ADMET Potency nan None 10.1021/jm00177a001
None ADMET T1/2 4.0 hr 10.1124/dmd.108.020479
None ADMET Vdss 3.5 L.kg-1 10.1021/jm030408h
None ADMET Vdss 3.5 L.kg-1 10.1124/dmd.108.020479
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None NON-PROTEIN TARGET Fu 0.7 None 10.1124/dmd.108.020479
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 1.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 2.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET IC50 nan None 10.1016/j.bmc.2010.01.068
None No relevant target LogD -2.0 None 10.1021/jm960073m
None No relevant target LogD -0.28 None 10.1021/jm0000564
None No relevant target LogD 0.22 None 10.1021/jm960073m
None No relevant target LogD 0.23 None 10.1021/jm0100990
None No relevant target LogD 1.19 None 10.1021/jm960073m
None No relevant target LogP 0.25 None 10.1021/jm00398a007
None No relevant target Log S -1.52 None 10.1016/s0960-894x(00)00172-4
None No relevant target Peff 8.0 ucm/s 10.1021/acs.jmedchem.9b01301
None No relevant target pKa 7.9 None 10.1021/jm0000564
None No relevant target pKa 8.2 None 10.1007/s11095-013-1232-z
None No relevant target pKa 8.2 None 10.1016/j.ejmech.2009.06.004
None No relevant target pKa 8.2 None 10.1021/jm030408h
None No relevant target pKa 8.22 None 10.1021/jm960073m
None No relevant target pKa 8.4 None 10.1124/dmd.110.035998
None No relevant target pKa 9.48 None 10.1124/dmd.112.050278
None Unchecked EC50 34700.0 nM 10.1016/j.bmc.2007.10.030
None Unchecked ED50 25.0 mg.kg-1 10.1021/jm020067s
None Unchecked ED50 27.0 mg.kg-1 10.1021/jm020067s
None Unchecked ED50 33.0 mg.kg-1 10.1021/jm020067s
None Unchecked Hepatotoxicity (acute) 3.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked IC50 4320.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked IC50 20910.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked Inhibition nan % 10.1016/j.bmc.2013.09.062
None Unchecked Ki 6900.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked Km 260.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked Km 370.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked Km 410.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked Km 430.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked Km 480.0 nM 10.1016/j.bmc.2013.09.062
None Unchecked Ratio 8.5 None 10.1021/jm00371a012
None Unchecked Ratio Ki 35.0 None 10.1021/jm701457j
None Unchecked Ratio Ki 72.0 None 10.1021/jm701457j
None Unchecked Vmax 4.06 nmol/min/mg 10.1016/j.bmc.2013.09.062
None Unchecked Vmax 4.41 nmol/min/mg 10.1016/j.bmc.2013.09.062
None Unchecked Vmax 8.04 nmol/min/mg 10.1016/j.bmc.2013.09.062
None Unchecked Vmax 12.4 nmol/min/mg 10.1016/j.bmc.2013.09.062
None Unchecked Vmax 12.51 nmol/min/mg 10.1016/j.bmc.2013.09.062

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001950 C=O.CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5>>COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314 MNXR148303
AKRT011910 COc1ccc2c3c1O[C@H]1C(=O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314>>COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@@]341 None
AKRT011911 COc1ccc2c3c1O[C@H]1C(=O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314>>COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314 1.1.1.247-RXN
AKRT011917 COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@@]341>>COc1ccc2c3c1O[C@H]1C(=O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314 None
AKRT011918 COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>COc1cc([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)c2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314 enzymemap_34879
AKRT011919 COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>COc1ccc2c3c1O[C@H]1[C@@H](O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314 R08261
AKRT011920 COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314>>C=O RXN-8152
AKRT011921 COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314>>CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5 RXN-8152
AKRT011922 COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314>>COc1ccc2c3c1O[C@H]1C(=O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314 enzymemap_3082
AKRT011923 COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314>>COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)NCC[C@]314 R08264