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name Structure Reference Source Properties Activities Metabolism

8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

AlkaPlorer ID: AK027415

Synonym: None

IUPAC Name: (19S)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

Structure

SMILES: CC[C@@]1(O)C(=O)OCC2=C1C=C1C3=NC4=CC=CC(N)=C4C=C3CN1C2=O

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InChI: InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1

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InChIKey: FUXVKZWTXQUGMW-FQEVSTJZSA-N

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Reference

PubChem CID: 72402

CAS: 91421-43-1

NPASS: NPC192674

Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 363.37300000000016

TPSA？: 107.44

MolLogP？: 1.6618

Number of H-Donors: 2

Number of H-Acceptors: 7

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition -5.64 % 10.6019/CHEMBL4296182
Candida albicans Candida albicans Inhibition 4.9 % 10.6019/CHEMBL4296182
Cryptococcus neoformans Cryptococcus neoformans Inhibition -6.8 % 10.6019/CHEMBL4296182
Escherichia coli Escherichia coli Inhibition 12.69 % 10.6019/CHEMBL4296182
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 1409.2 nM None
Herpes simplex virus (type 1 / strain 17) Alpha trans-inducing protein (VP16) IC50 1991.0 nM None
Homo sapiens 786-0 GI50 10.0 nM None
Homo sapiens A498 GI50 79.43 nM None
Homo sapiens A498 ID50 10.0 ng ml-1 10.1016/s0960-894x(02)00388-8
Homo sapiens A549 GI50 18.79 nM None
Homo sapiens ACHN GI50 10.0 nM None
Homo sapiens Ataxin-2 Potency 5011.9 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 58.0 nM None
Homo sapiens ATP-binding cassette sub-family G member 2 Activity nan None None
Homo sapiens ATP-dependent DNA helicase Q1 Potency 39810.7 nM None
Homo sapiens BJ EC50 7.18 nM None
Homo sapiens Bloom syndrome protein Potency 28183.8 nM None
Homo sapiens BT-549 GI50 68.39 nM None
Homo sapiens CAKI-1 GI50 10.0 nM None
Homo sapiens CCRF-CEM GI50 36.9 nM None
Homo sapiens COLO 205 GI50 156.68 nM None
Homo sapiens COLO 205 IC50 6.6 nM 10.1021/jm990124q
Homo sapiens DLD-1 GI50 566.24 nM None
Homo sapiens DMS-114 GI50 10.0 nM None
Homo sapiens DMS-273 GI50 10.0 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 35481.3 nM None
Homo sapiens DNA polymerase beta Potency 50118.7 nM None
Homo sapiens DNA polymerase eta Potency 22387.2 nM None
Homo sapiens DNA polymerase iota Potency 79432.8 nM None
Homo sapiens DNA polymerase kappa Potency 79432.8 nM None
Homo sapiens DNA topoisomerase I Activity 87.0 % 10.1021/np034084b
Homo sapiens DNA topoisomerase I CC50 900.0 nM 10.1021/jm00105a017
Homo sapiens DNA topoisomerase I IC50 110.0 nM 10.1021/jm00070a013
Homo sapiens DNA topoisomerase I IC50 1800.0 nM 10.1016/S0960-894X(97)00105-4
Homo sapiens DNA topoisomerase I IC50 4200.0 nM 10.1016/0960-894X(96)00083-2
Homo sapiens DU-145 GI50 10.0 nM None
Homo sapiens EKVX GI50 340.41 nM None
Homo sapiens EVSA-T ID50 3.2 ng ml-1 10.1016/s0960-894x(02)00388-8
Homo sapiens Flap endonuclease 1 Potency 17782.8 nM None
Homo sapiens Geminin Potency 2059.6 nM None
Homo sapiens Guanine nucleotide-binding protein G(s), subunit alpha Potency 15848.9 nM None
Homo sapiens HCC 2998 GI50 110.66 nM None
Homo sapiens HCT-116 GI50 27.23 nM None
Homo sapiens HCT-15 GI50 196.79 nM None
Homo sapiens HepG2 IC50 3.5 nM 10.1021/jm990124q
Homo sapiens HepG2 Potency 112.2 nM None
Homo sapiens Histone deacetylase 6 Inhibition -20.21 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -1.39 % 10.6019/CHEMBL4808148
Homo sapiens HL-60 GI50 10.0 nM None
Homo sapiens HOP-18 GI50 27.73 nM None
Homo sapiens HOP-62 GI50 10.0 nM None
Homo sapiens HOP-92 GI50 35.65 nM None
Homo sapiens Hs-578T GI50 4216.97 nM None
Homo sapiens HT-29 Control 25.0 % 10.1021/jm00070a013
Homo sapiens HT-29 GI50 63.24 nM None
Homo sapiens HT-29 IC50 7.4 nM 10.1021/jm990124q
Homo sapiens IGROV-1 GI50 246.04 nM None
Homo sapiens IGROV-1 ID50 3.2 ng ml-1 10.1016/s0960-894x(02)00388-8
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 2059.6 nM None
Homo sapiens K562 GI50 112.2 nM None
Homo sapiens KM12 GI50 230.14 nM None
Homo sapiens KM-20L2 GI50 64.27 nM None
Homo sapiens LOX IMVI GI50 10.0 nM None
Homo sapiens LXFL 529 GI50 243.78 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 25118.9 nM None
Homo sapiens M14 GI50 11.32 nM None
Homo sapiens M19-MEL GI50 19.82 nM None
Homo sapiens M19-MEL ID50 24.0 ng ml-1 10.1016/s0960-894x(02)00388-8
Homo sapiens Malme-3M GI50 78.52 nM None
Homo sapiens MCF7 GI50 10.0 nM None
Homo sapiens MCF7 ID50 3.2 ng ml-1 10.1016/s0960-894x(02)00388-8
Homo sapiens MDA-MB-231 GI50 272.27 nM None
Homo sapiens MDA-MB-435 GI50 118.03 nM None
Homo sapiens MDA-N GI50 228.56 nM None
Homo sapiens microRNA 21 Potency 1309.2 nM None
Homo sapiens Microtubule-associated protein tau Potency 17782.8 nM None
Homo sapiens MOLT-4 GI50 10.0 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 461.1 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 562.3 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 1158.2 nM None
Homo sapiens Muscleblind-like protein 1 Potency 8912.5 nM None
Homo sapiens NCI/ADR-RES GI50 12.79 nM None
Homo sapiens NCI-H226 GI50 10.21 nM None
Homo sapiens NCI-H226 ID50 7.0 ng ml-1 10.1016/s0960-894x(02)00388-8
Homo sapiens NCI-H23 GI50 10.0 nM None
Homo sapiens NCI-H322M GI50 103.51 nM None
Homo sapiens NCI-H460 GI50 10.0 nM None
Homo sapiens NCI-H522 GI50 18.11 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 259.3 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 651.3 nM None
Homo sapiens OVCAR-3 GI50 207.01 nM None
Homo sapiens OVCAR-4 GI50 237.68 nM None
Homo sapiens OVCAR-5 GI50 127.94 nM None
Homo sapiens OVCAR-8 GI50 14.83 nM None
Homo sapiens Paired box protein Pax-8 AC50 260.0 nM None
Homo sapiens Parathyroid hormone receptor Potency 44668.4 nM None
Homo sapiens PC-3 GI50 72.78 nM None
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 31622.8 nM None
Homo sapiens Photoreceptor-specific nuclear receptor IC50 895.89 nM None
Homo sapiens Ras-related protein Rab-9A Potency 2238.7 nM None
Homo sapiens RPMI-8226 GI50 76.38 nM None
Homo sapiens RXF 393 GI50 40.83 nM None
Homo sapiens RXF 631 GI50 37.5 nM None
Homo sapiens SF-268 GI50 10.0 nM None
Homo sapiens SF-295 GI50 10.0 nM None
Homo sapiens SF-539 GI50 10.0 nM None
Homo sapiens SK-MEL-2 GI50 232.81 nM None
Homo sapiens SK-MEL-28 GI50 177.01 nM None
Homo sapiens SK-MEL-5 GI50 11.78 nM None
Homo sapiens SK-OV-3 GI50 15.7 nM None
Homo sapiens SN12C GI50 10.0 nM None
Homo sapiens SN12K1 GI50 22.7 nM None
Homo sapiens SNB-19 GI50 10.0 nM None
Homo sapiens SNB-75 GI50 11.48 nM None
Homo sapiens SNB-78 GI50 574.12 nM None
Homo sapiens Sphingomyelin phosphodiesterase Potency 15848.9 nM None
Homo sapiens SR GI50 215.28 nM None
Homo sapiens SW-620 GI50 32.06 nM None
Homo sapiens T47D GI50 10.0 nM None
Homo sapiens TK-10 GI50 1629.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 130.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 163.6 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 39810.7 nM None
Homo sapiens U-251 GI50 10.76 nM None
Homo sapiens UACC-257 GI50 57.15 nM None
Homo sapiens UACC-62 GI50 10.21 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 35481.3 nM None
Homo sapiens UO-31 GI50 17.5 nM None
Homo sapiens WiDr ID50 3.2 ng ml-1 10.1016/s0960-894x(02)00388-8
Homo sapiens XF498 GI50 143.22 nM None
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition 8.25 % 10.6019/CHEMBL4296182
Mus musculus Heat shock factor protein 1 AbsAC40_uM 15.89 uM None
Mus musculus Heat shock factor protein 1 EC50 260000.0 nM None
Mus musculus L1210 Active dose range 5.0 mg kg-1 10.1021/jm00393a016
Mus musculus L1210 IC50 12.0 nM 10.1021/jm00105a017
Mus musculus L1210 IC50 12.7 nM 10.1016/0960-894X(96)00083-2
Mus musculus L1210 IC50 12.7 nM 10.1016/S0960-894X(97)00105-4
Mus musculus L1210 KE 5.97 None 10.1021/jm00070a013
Mus musculus L1210 Toxic dose 10.0 mg kg-1 10.1021/jm00393a016
Mus musculus Mus musculus Cures 3.0 None 10.1021/jm00070a013
Mus musculus Mus musculus Highest active dose 0.6 mg kg-1 10.1021/jm00070a013
Mus musculus Mus musculus ILS 94.0 % 10.1021/jm00105a017
Mus musculus Mus musculus MTD 8.9 uM kg-1 10.1021/jm00105a017
Mus musculus Mus musculus No. of cures 4.0 None 10.1021/jm00393a016
Mus musculus Mus musculus T/C 1.15 None 10.1021/jm00070a013
Mus musculus Mus musculus T/C 2.44 None 10.1021/jm00070a013
Mus musculus Mus musculus T/C 5.97 % 10.1021/jm00393a016
Mus musculus Mus musculus T/C 138.0 % 10.1016/0960-894X(96)00083-2
Mus musculus Mus musculus T/C 163.0 % 10.1016/0960-894X(96)00083-2
Mus musculus Mus musculus T/C 361.0 % 10.1021/jm00070a013
Mus musculus Mus musculus T/C 361.0 % 10.1021/jm00393a016
Mus musculus Mus musculus Toxic dose 10.0 mg kg-1 10.1021/jm00070a013
Mus musculus Nuclear receptor ROR-gamma Potency 20.0 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 354.8 nM None
Mus musculus P338 Active dose range 2.5 mg kg-1 10.1021/jm00161a035
Mus musculus P338 No. of cures 4.0 None 10.1021/jm00161a035
Mus musculus P338 T/C 5.86 % 10.1021/jm00161a035
Mus musculus P338 T/C 348.0 % 10.1021/jm00161a035
Mus musculus P338 Toxic dose 10.0 mg kg-1 10.1021/jm00161a035
Mus musculus P388 GI50 11.91 nM None
Mus musculus P388/ADR GI50 17.38 nM None
Plasmodium falciparum Plasmodium falciparum Potency 1168.9 nM None
Plasmodium falciparum Plasmodium falciparum Potency 1852.6 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition 22.5 % 10.6019/CHEMBL4296182
Rattus norvegicus INS1 AC50 2132.0 nM None
Schistosoma mansoni Thioredoxin glutathione reductase Potency 50118.7 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 1.64 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 7.6 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.03 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.01 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 80.32 % 10.21203/rs.3.rs-23951/v1
Staphylococcus aureus Staphylococcus aureus Inhibition 34.7 % 10.6019/CHEMBL4296182
None ADMET CL 6.5 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET ED50 0.02 ug ml-1 10.1021/jm00393a016
None ADMET IC50 1.0 nM 10.1021/jm101354u
None ADMET IC50 90.0 nM 10.1021/jm101354u
None ADMET IC90 700.0 nM 10.1021/jm101354u
None ADMET MRT 5.6 hr 10.1124/dmd.108.020479
None ADMET Ratio 75.0 None 10.1021/jm101354u
None ADMET Ratio 88.0 None 10.1021/jm101354u
None ADMET T1/2 0.2983 hr 10.1021/jm00027a005
None ADMET T1/2 0.39 hr 10.1021/jm00027a005
None ADMET T1/2 7.0 hr 10.1124/dmd.108.020479
None ADMET Vdss 2.2 L.kg-1 10.1124/dmd.108.020479
None NCI-H928 IC50 7.9 nM 10.1021/jm990124q
None NON-PROTEIN TARGET AC50 2470.0 nM None
None NON-PROTEIN TARGET Fu 0.003 None 10.1124/dmd.108.020479
None NON-PROTEIN TARGET IC50 8.5 nM 10.1021/jm990124q
None No relevant target AC50 260.0 nM None
None No relevant target Solubility 0.06 mg kg-1 10.1021/jm990124q
None No relevant target Solubility 6.0 ug.mL-1 10.1021/jm990124q
None Unchecked AC50 260.0 nM None
None Unchecked AC50 348.0 nM None
None Unchecked AC50 463.0 nM None
None Unchecked Control 73.0 % 10.1021/jm00070a013
None Unchecked EC50 350000.0 nM None
None Unchecked IC50 160.0 nM None
None Unchecked IC50 620.0 nM None
None Unchecked IC50 6020.0 nM None
None Unchecked IC50 80000.0 nM None
None Unchecked Potency 410.9 nM None
None Unchecked Potency 920.0 nM None
None Unchecked Potency 1000.0 nM None
None Unchecked Potency 1258.9 nM None
None Unchecked Potency 1299.5 nM None
None Unchecked Potency 10000.0 nM None

Metabolism Information