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Nalfurafine

AlkaPlorer ID: AK005793

Synonym: None

IUPAC Name: (E)-N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-3-(furan-3-yl)-N-methylprop-2-enamide

Structure

SMILES: CN([C@@H]1CC[C@]2([C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3CC6CC6)O)C(=O)/C=C/C7=COC=C7

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InChI: InChI=1S/C28H32N2O5/c1-29(23(32)7-4-18-9-13-34-16-18)20-8-10-28(33)22-14-19-5-6-21(31)25-24(19)27(28,26(20)35-25)11-12-30(22)15-17-2-3-17/h4-7,9,13,16-17,20,22,26,31,33H,2-3,8,10-12,14-15H2,1H3/b7-4+/t20-,22-,26+,27+,28-/m1/s1

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InChIKey: XGZZHZMWIXFATA-UEZBDDGYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 476.57300000000026

TPSA？: 86.38000000000001

MolLogP？: 3.0897000000000014

Number of H-Donors: 2

Number of H-Acceptors: 6

RingCount: 7

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Kappa opioid receptor Ki 0.17 nM 10.1016/j.bmcl.2015.09.040
Cavia porcellus Kappa opioid receptor Ki 0.18 nM 10.1016/j.bmcl.2014.09.029
Cavia porcellus Kappa opioid receptor Ki 0.225 nM 10.1016/j.bmc.2010.12.035
Cavia porcellus Kappa opioid receptor Ki 0.225 nM 10.1016/j.bmcl.2010.07.035
Cavia porcellus Mu opioid receptor Ki 0.39 nM 10.1016/j.bmcl.2015.09.040
Cavia porcellus Mu opioid receptor Ki 0.582 nM 10.1016/j.bmc.2010.12.035
Cavia porcellus Mu opioid receptor Ki 0.582 nM 10.1016/j.bmcl.2010.07.035
Cavia porcellus Opioid receptor (mu and kappa) Ratio Ki 2.6 None 10.1016/j.bmc.2010.12.035
Cavia porcellus Opioid receptor (mu and kappa) Ratio Ki 2.6 None 10.1016/j.bmcl.2010.07.035
Homo sapiens Adhesion G-protein coupled receptor F1 %Inhib (Mean) -17.42 % 10.6019/CHEMBL5209801
Homo sapiens Adhesion G-protein coupled receptor F1 %Max (Mean) 19.29 % 10.6019/CHEMBL5209801
Homo sapiens Alpha-2a adrenergic receptor %Inhib (Mean) -39.6 % 10.6019/CHEMBL5209801
Homo sapiens Alpha-2a adrenergic receptor %Max (Mean) 0.1 % 10.6019/CHEMBL5209801
Homo sapiens Apelin receptor %Inhib (Mean) -62.83 % 10.6019/CHEMBL5209801
Homo sapiens Apelin receptor %Max (Mean) 4.029 % 10.6019/CHEMBL5209801
Homo sapiens Beta-2 adrenergic receptor %Inhib (Mean) -79.41 % 10.6019/CHEMBL5209801
Homo sapiens Beta-2 adrenergic receptor %Max (Mean) -1.326 % 10.6019/CHEMBL5209801
Homo sapiens Bromodomain-containing protein 4 Delta TM -1.01 C None
Homo sapiens C5a anaphylatoxin chemotactic receptor %Inhib (Mean) -47.15 % 10.6019/CHEMBL5209801
Homo sapiens C5a anaphylatoxin chemotactic receptor %Max (Mean) -2.333 % 10.6019/CHEMBL5209801
Homo sapiens Casein kinase I delta Delta TM -0.01 C None
Homo sapiens C-X3-C chemokine receptor 1 %Inhib (Mean) -83.17 % 10.6019/CHEMBL5209801
Homo sapiens C-X3-C chemokine receptor 1 %Max (Mean) -2.46 % 10.6019/CHEMBL5209801
Homo sapiens Cyclin-dependent kinase 2 Delta TM 0.6 C None
Homo sapiens Delta opioid receptor EC50 74.1 nM 10.1016/j.bmcl.2014.09.029
Homo sapiens Delta opioid receptor Emax 55.2 % 10.1016/j.bmcl.2014.09.029
Homo sapiens Delta opioid receptor Ki 36.5 nM 10.1016/j.bmcl.2022.128527
Homo sapiens Fibroblast Growth Rate 0.55 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast growth factor receptor 3 Delta TM 0.13 C None
Homo sapiens Glucagon-like peptide 1 receptor %Inhib (Mean) -51.7 % 10.6019/CHEMBL5209801
Homo sapiens Glucagon-like peptide 1 receptor %Max (Mean) -1.299 % 10.6019/CHEMBL5209801
Homo sapiens Glucose-dependent insulinotropic receptor %Inhib (Mean) -41.29 % 10.6019/CHEMBL5209801
Homo sapiens Glucose-dependent insulinotropic receptor %Max (Mean) -0.529 % 10.6019/CHEMBL5209801
Homo sapiens Glycogen synthase kinase-3 beta Delta TM -0.5 C None
Homo sapiens G-protein coupled receptor 120 %Inhib (Mean) -64.71 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 120 %Max (Mean) -1.71 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 35 %Inhib (Mean) -41.22 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 35 %Max (Mean) 4.412 % 10.6019/CHEMBL5209801
Homo sapiens HEK-293T Growth Rate 0.49 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate 0.87 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate 0.91 None 10.6019/CHEMBL5058564
Homo sapiens Histone deacetylase 6 Inhibition -5.38 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -3.78 % 10.6019/CHEMBL4808148
Homo sapiens Kappa opioid receptor Activity 100.0 % 10.1016/j.bmcl.2015.09.040
Homo sapiens Kappa opioid receptor EC50 0.025 nM 10.1016/j.bmc.2007.10.067
Homo sapiens Kappa opioid receptor EC50 0.034 nM 10.1016/j.bmcl.2015.09.040
Homo sapiens Kappa opioid receptor EC50 0.05 nM 10.1016/j.bmcl.2014.09.029
Homo sapiens Kappa opioid receptor EC50 1.4 nM 10.1021/acs.jmedchem.8b00435
Homo sapiens Kappa opioid receptor EC50 110.0 nM 10.1021/acs.jmedchem.8b00435
Homo sapiens Kappa opioid receptor Emax 98.1 % 10.1016/j.bmcl.2014.09.029
Homo sapiens Kappa opioid receptor Emax 99.0 % 10.1021/acs.jmedchem.8b00435
Homo sapiens Kappa opioid receptor Emax 100.0 % 10.1021/acs.jmedchem.8b00435
Homo sapiens Kappa opioid receptor Inhibition 40.0 % 10.1039/C5MD00414D
Homo sapiens Kappa opioid receptor Ki 0.019 nM 10.1016/j.bmcl.2022.128527
Homo sapiens Kappa opioid receptor Ki 0.23 nM 10.1016/j.bmc.2013.03.026
Homo sapiens Kappa opioid receptor Ki 0.23 nM 10.1016/j.bmcl.2012.03.001
Homo sapiens Kappa opioid receptor Ki 170.0 nM 10.1016/j.bmcl.2015.09.040
Homo sapiens Lipoxin A4 receptor %Inhib (Mean) -28.55 % 10.6019/CHEMBL5209801
Homo sapiens Lipoxin A4 receptor %Max (Mean) -2.621 % 10.6019/CHEMBL5209801
Homo sapiens MAP kinase ERK1 EC50 0.55 nM 10.1016/j.ejmech.2019.111701
Homo sapiens MAP kinase ERK2 Delta TM -0.01 C None
Homo sapiens MAP kinase ERK2 EC50 0.55 nM 10.1016/j.ejmech.2019.111701
Homo sapiens MAP kinase p38 EC50 5.2 nM 10.1016/j.ejmech.2019.111701
Homo sapiens Mu opioid receptor EC50 0.72 nM 10.1016/j.bmcl.2014.09.029
Homo sapiens Mu opioid receptor Emax 70.4 % 10.1016/j.bmcl.2014.09.029
Homo sapiens Mu opioid receptor Ki 0.7 nM 10.1016/j.bmcl.2022.128527
Homo sapiens Peregrin Delta TM -1.68 C None
Homo sapiens Serine/threonine-protein kinase Aurora-A Delta TM -0.22 C None
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 %Inhib (Mean) -64.12 % 10.6019/CHEMBL5209801
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 %Max (Mean) 10.8 % 10.6019/CHEMBL5209801
Homo sapiens Transcription intermediary factor 1-alpha Delta TM -0.04 C None
Homo sapiens Type-1 angiotensin II receptor %Inhib (Mean) -30.04 % 10.6019/CHEMBL5209801
Homo sapiens Type-1 angiotensin II receptor %Max (Mean) -2.54 % 10.6019/CHEMBL5209801
Homo sapiens Tyrosine-protein kinase ABL Delta TM 0.68 C None
Homo sapiens U2OS Growth Rate -0.09 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.56 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.68 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.77 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.82 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.88 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 1.0 None 10.6019/CHEMBL5058564
Mus musculus Delta opioid receptor Ki 51.3 nM 10.1016/j.bmcl.2014.09.029
Mus musculus Mu opioid receptor Ki 0.43 nM 10.1016/j.bmcl.2014.09.029
Mus musculus Mus musculus Activity nan None 10.1016/j.bmcl.2020.127360
Mus musculus Mus musculus ED50 0.0033 mg.kg-1 10.1016/j.bmc.2010.12.035
Rattus norvegicus Delta opioid receptor Ki 0.37 nM 10.1016/j.bmcl.2015.09.040
Rattus norvegicus Kappa opioid receptor EC50 0.5 nM 10.1021/acs.jmedchem.8b00435
Rattus norvegicus Kappa opioid receptor EC50 5.2 nM 10.1021/acs.jmedchem.8b00435
Rattus norvegicus Kappa opioid receptor Emax 100.0 % 10.1021/acs.jmedchem.8b00435
Rattus norvegicus Kappa opioid receptor Emax 110.0 % 10.1021/acs.jmedchem.8b00435
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1349 None 10.1101/2020.04.21.054387
Trichomonas vaginalis Trichomonas vaginalis MIC 80000.0 nM 10.1016/j.bmc.2017.06.026
None ADMET Activity nan None 10.1016/j.bmcl.2020.127360
None ADMET Activity nan None 10.1021/acs.jmedchem.2c00014
None No relevant target pKa 9.4 None 10.1016/j.bmcl.2020.127360
None Unchecked Ki 96.5 nM 10.1016/j.bmc.2010.12.035
None Unchecked Ki 96.5 nM 10.1016/j.bmcl.2010.07.035
None Unchecked Ratio Ki 2.42 None 10.1016/j.bmcl.2014.09.029
None Unchecked Ratio Ki 36.8 None 10.1016/j.bmcl.2022.128527
None Unchecked Ratio Ki 166.0 None 10.1016/j.bmc.2010.12.035
None Unchecked Ratio Ki 429.0 None 10.1016/j.bmcl.2010.07.035
None Unchecked Ratio Ki 456.0 None 10.1016/j.bmc.2010.12.035
None Unchecked Ratio Ki 1921.0 None 10.1016/j.bmcl.2022.128527
None Unchecked Selectivity ratio 100.0 None 10.1016/j.bmc.2007.10.067

Metabolism Information