Navigation

name Structure Reference Source Properties Activities Metabolism

Hydromorphone

AlkaPlorer ID: AK001469

Synonym: None

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

Structure

SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3C(=O)CC4

copy

InChI: InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1

copy

InChIKey: WVLOADHCBXTIJK-YNHQPCIGSA-N

copy

Source

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

Properties Information

Molecule Weight: 285.3430000000001

TPSA？: 49.77

MolLogP？: 1.6302999999999999

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
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 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 3A4 Inhibition nan % 10.1021/tx300075j
Homo sapiens Delta opioid receptor Ki 38.0 nM 10.1016/j.bmcl.2009.02.078
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 3.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens F 24.0 % 10.1016/j.bmc.2007.08.060
Homo sapiens Kappa opioid receptor EC50 11.0 nM 10.1016/j.bmcl.2009.02.078
Homo sapiens Kappa opioid receptor Emax 78.0 % 10.1016/j.bmcl.2009.02.078
Homo sapiens Kappa opioid receptor IC50 nan None 10.1016/j.bmcl.2009.02.078
Homo sapiens Kappa opioid receptor Imax nan None 10.1016/j.bmcl.2009.02.078
Homo sapiens Kappa opioid receptor Ki 2.8 nM 10.1016/j.bmcl.2009.02.078
Homo sapiens Liver microsomes Activity nan None 10.1021/tx300075j
Homo sapiens Liver microsomes Stability nan % 10.1021/tx300075j
Homo sapiens Mu opioid receptor EC50 2.6 nM 10.1016/j.bmcl.2009.02.078
Homo sapiens Mu opioid receptor Emax 70.0 % 10.1016/j.bmcl.2009.02.078
Homo sapiens Mu opioid receptor IC50 nan None 10.1016/j.bmcl.2009.02.078
Homo sapiens Mu opioid receptor Imax nan None 10.1016/j.bmcl.2009.02.078
Homo sapiens Mu opioid receptor Ki 0.28 nM 10.1016/j.bmcl.2009.02.078
Homo sapiens Skin log Kp -8.13 None 10.1016/j.bmc.2007.07.050
Homo sapiens Solute carrier family 22 member 1 Activity nan None 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 FC 1.7 None 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 FC 1.9 None 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 FC 2.0 None 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 IC50 137970.0 nM 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 Km 56100.0 nM 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 1 Vmax 33.0 pmol/min/mg 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 3 Km 755000.0 nM 10.1021/acs.jmedchem.9b01301
Homo sapiens Solute carrier family 22 member 3 Vmax 672.5 pmol/min/mg 10.1021/acs.jmedchem.9b01301
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 14.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-8 Activity 29.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-8 Activity 33.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 118.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 530.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 617.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 856.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 1028.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 1550.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens Whole blood Retention_time 1.84 min 10.1007/s00044-012-9977-1
Mus musculus Mus musculus ED50 0.08 mg.kg-1 10.1021/jm00350a019
Mus musculus Mus musculus ED50 0.25 uM 10.1021/jm00176a012
Mus musculus Mus musculus ED50 0.25 umol.kg-1 10.1021/jm00138a015
Mus musculus Mus musculus ED50 0.25 umol.kg-1 10.1021/jm00176a013
Mus musculus Mus musculus ED50 0.25 umol.kg-1 10.1021/jm00186a025
Mus musculus Mus musculus ED50 0.25 umol.kg-1 10.1021/jm00361a019
Mus musculus Mus musculus ED50 0.3 umol.kg-1 10.1021/jm00144a015
Rattus norvegicus Rattus norvegicus ED50 1.3 umol.kg-1 10.1021/jm00138a015
Rattus norvegicus Rattus norvegicus ED50 1.3 umol.kg-1 10.1021/jm00144a015
Rattus norvegicus Rattus norvegicus ED50 1.34 uM 10.1021/jm00176a012
Rattus norvegicus Rattus norvegicus ED50 1.34 umol.kg-1 10.1021/jm00176a013
Rattus norvegicus Rattus norvegicus ED50 1.34 umol.kg-1 10.1021/jm00186a025
Rattus norvegicus Rattus norvegicus ED50 78.0 nmol 10.1021/acs.jmedchem.5b00841
None ADMET CL 28.0 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET Cmax 40.0 nM 10.1021/acs.jmedchem.9b01301
None ADMET fCmax 0.03 uM 10.1021/acs.jmedchem.9b01301
None ADMET fCmax 0.72 uM 10.1021/acs.jmedchem.9b01301
None ADMET MRT 2.6 hr 10.1124/dmd.108.020479
None ADMET T1/2 2.3 hr 10.1124/dmd.108.020479
None ADMET Vdss 4.3 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 1.0 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 5.0 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 1.0 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 1.0 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 1.0 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 0.86 None 10.1124/dmd.108.020479
None No relevant target Peff 1.7 ucm/s 10.1021/acs.jmedchem.9b01301
None No relevant target Solubility 500000.0 nM 10.1016/j.bmcl.2010.10.068
None Unchecked Activity nan None 10.1021/acs.jmedchem.9b01301
None Unchecked Ratio 0.0002 None 10.1021/acs.jmedchem.9b01301
None Unchecked Ratio 0.005 None 10.1021/acs.jmedchem.9b01301
None Unchecked Ratio Ki 10.0 None 10.1016/j.bmcl.2009.02.078
None Unchecked Ratio Ki 136.0 None 10.1016/j.bmcl.2009.02.078

Metabolism Information