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name Structure Reference Source Properties Activities Metabolism

N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,?.0¹²,¹?]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide

AlkaPlorer ID: AK004619

Synonym: None

IUPAC Name: (6aR,9R)-N-(1-hydroxybutan-2-yl)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide

Structure

SMILES: CCC(CO)N=C(O)[C@@H]1C=C2C3=C4C(=CN(C)C4=CC=C3)C[C@H]2N(C)C1

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InChI: InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15?,19-/m1/s1

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InChIKey: KPJZHOPZRAFDTN-NQUBZZJWSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Apis cerana Apis Apidae Hymenoptera Insecta Arthropoda Metazoa Eukaryota

Properties Information

Molecule Weight: 353.4660000000001

TPSA？: 60.99000000000001

MolLogP？: 2.775400000000001

Number of H-Donors: 2

Number of H-Acceptors: 4

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Ileum Activity 37.0 % 10.1021/np50111a020
Cavia porcellus Ileum Activity nan None 10.1021/np50111a020
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 Bile salt export pump IC50 33070.0 nM 10.1124/dmd.112.047068
Homo sapiens HepG2 IC50 10000.0 nM 10.1073/pnas.1118370109
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 13.0 % 10.1016/j.bmc.2007.08.060
Homo sapiens Serotonin 2a (5-HT2a) receptor Inhibition 97.0 % 10.1021/jm300573d
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 1.585 nM 10.1021/jm300573d
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 12.59 nM 10.1021/jm030841r
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 79.43 nM 10.1016/j.ejmech.2019.111705
Homo sapiens Sigma opioid receptor IC50 912.01 nM 10.1021/jm00050a008
Homo sapiens Sodium channel alpha subunits; brain (Types I, II, III) Inhibition 17.8 % 10.1021/jm00381a019
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 ID50 0.52 mg.kg-1 10.1021/jm00395a013
Plasmodium berghei Plasmodium berghei IC50 356.0 nM 10.1073/pnas.1118370109
Plasmodium falciparum Plasmodium falciparum IC50 5000.0 nM 10.1073/pnas.1118370109
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 Rattus norvegicus IC50 7.413 nM 10.1021/jm00159a017
Rattus norvegicus Rattus norvegicus IC50 13.49 nM 10.1021/jm00159a017
Rattus norvegicus Rattus norvegicus ID50 0.4 mg.kg-1 10.1021/jm00395a013
Rattus norvegicus Rattus norvegicus Inhibition 78.9 % 10.1021/jm00035a012
Rattus norvegicus Rattus norvegicus Ki 1.92 nM 10.1021/jm00159a017
Rattus norvegicus Rattus norvegicus Ki 6.74 nM 10.1021/jm00159a017
Rattus norvegicus Serotonin 1 (5-HT1) receptor IC50 31.62 nM 10.1021/jm00395a013
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Activity 11.0 % 10.1016/j.ejmech.2015.04.046
Rattus norvegicus Serotonin 1a (5-HT1a) receptor Activity 18.0 % 10.1016/j.ejmech.2015.04.046
Rattus norvegicus Serotonin 2 (5-HT2) receptor IC50 5.012 nM 10.1021/jm00395a013
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 1.445 nM 10.1016/S0960-894X(01)81054-4
Rattus norvegicus Serotonin 2 (5-HT2) receptor Ki 5.3 nM 10.1021/jm9706832
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Ki 1.445 nM 10.1021/jm00042a009
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Ki 1.6 nM 10.1021/jm00014a021
Rattus norvegicus Serotonin 2a (5-HT2a) receptor Ki 1.995 nM 10.1021/jm990151g
Rattus norvegicus Serotonin 7 (5-HT7) receptor Ki 12.59 nM 10.1016/s0960-894x(00)00166-9
Sus scrofa LLC-PK1 Ratio 4.3 None 10.1021/ml300314h
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 Binding energy 12.3 kCal mol-1 10.1021/jm00378a021
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 LTKB_BD DILI severity score nan None 10.1016/j.drudis.2011.05.007
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) 0.0 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) 1.0 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 Unchecked Hepatotoxicity (acute) 0.0 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) 0.0 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 20.0 nM 10.1021/np50122a017
None Unchecked Ki 5.7 nM 10.1021/np960644d
None Unchecked Ki 6.8 nM 10.1021/np50094a001
None Unchecked Ki 14.8 nM 10.1021/np50094a001

Metabolism Information