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Rutaecarpine

AlkaPlorer ID: AK000405

Synonym: None

IUPAC Name: 3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one

Structure

SMILES: O=C1C2=CC=CC=C2N=C2C3=C(CCN21)C1=CC=CC=C1N3

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InChI: InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2

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InChIKey: ACVGWSKVRYFWRP-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 287.32199999999995

TPSA？: 50.68

MolLogP？: 3.100900000000001

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Danio rerio Danio rerio IC50 25490.0 nM None
Electrophorus electricus Acetylcholinesterase IC50 100000.0 nM 10.1016/j.ejmech.2009.12.044
Electrophorus electricus Acetylcholinesterase IC50 100000.0 nM 10.1016/j.ejmech.2019.05.055
Electrophorus electricus Acetylcholinesterase Inhibition -4.0 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase IC50 100000.0 nM 10.1016/j.ejmech.2009.12.044
Equus caballus Cholinesterase IC50 100000.0 nM 10.1016/j.ejmech.2019.05.055
Equus caballus Cholinesterase Inhibition -27.56 % 10.1016/j.bmc.2012.09.040
Equus caballus Ferritin light chain Potency 39810.7 nM None
Escherichia coli K-12 Beta-lactamase AmpC Potency 6309.6 nM None
Homo sapiens 78 kDa glucose-regulated protein Potency 261.2 nM None
Homo sapiens A549 GI50 14500.0 nM 10.1016/0960-894X(95)00046-V
Homo sapiens A549 GI50 14521.12 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 28183.8 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 35481.3 nM None
Homo sapiens Amyloid-beta A4 protein Inhibition 11.25 % 10.1016/j.ejmech.2019.05.055
Homo sapiens Ataxin-2 Potency 631.0 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 1457.5 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 2818.4 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 3262.9 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 8196.1 nM None
Homo sapiens Bloom syndrome protein Potency 19952.6 nM None
Homo sapiens CAKI-1 GI50 9204.5 nM None
Homo sapiens CCD-18Co IC50 50000.0 nM 10.1021/acs.jnatprod.2c00224
Homo sapiens CCD-841CoN IC50 50000.0 nM 10.1021/acs.jnatprod.2c00224
Homo sapiens CCRF-CEM GI50 18879.91 nM None
Homo sapiens CCRF-CEM GI50 18900.0 nM 10.1016/0960-894X(95)00046-V
Homo sapiens Cellular tumor antigen p53 Potency 2511.9 nM None
Homo sapiens Cellular tumor antigen p53 Potency 12589.3 nM None
Homo sapiens Cerebroside-sulfatase Potency 21.3 nM None
Homo sapiens Chromobox protein homolog 1 Potency 79432.8 nM None
Homo sapiens COLO 205 GI50 21777.1 nM None
Homo sapiens Cyclooxygenase-1 IC50 8700.0 nM 10.1016/j.bmc.2012.09.069
Homo sapiens Cyclooxygenase-1 IC50 8700.0 nM 10.1021/np049655u
Homo sapiens Cyclooxygenase-2 IC50 280.0 nM 10.1016/j.bmc.2012.09.069
Homo sapiens Cyclooxygenase-2 IC50 300.0 nM 10.1021/np049655u
Homo sapiens Cytochrome P450 1A1 IC50 260.0 nM 10.1016/s0960-894x(03)00469-4
Homo sapiens Cytochrome P450 1A2 AC50 316.23 nM None
Homo sapiens Cytochrome P450 1A2 IC50 22.0 nM 10.1016/s0960-894x(03)00469-4
Homo sapiens Cytochrome P450 1B1 IC50 55.0 nM 10.1016/j.ejmech.2017.04.042
Homo sapiens Cytochrome P450 1B1 IC50 55.0 nM 10.1016/s0960-894x(03)00469-4
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 3981.07 nM None
Homo sapiens Cytochrome P450 3A4 Ki 107700.0 nM 10.2174/138920005774330639
Homo sapiens Cytochrome P450 3A4 Kinact 0.387 min-1 10.2174/138920005774330639
Homo sapiens Cytochrome P450 3A4 Potency 3981.1 nM None
Homo sapiens DNA polymerase beta Potency 44668.4 nM None
Homo sapiens DNA polymerase iota Potency 22.4 nM None
Homo sapiens DU-145 GI50 17378.01 nM None
Homo sapiens EKVX GI50 20653.8 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 25118.9 nM None
Homo sapiens HCT-116 GI50 17538.81 nM None
Homo sapiens HCT-116 IC50 31100.0 nM 10.1021/acs.jnatprod.2c00224
Homo sapiens HCT-15 GI50 10000.0 nM None
Homo sapiens HCT-15 IC50 50000.0 nM 10.1021/acs.jnatprod.2c00224
Homo sapiens HEK293 Activity nan None 10.1021/acs.jnatprod.5b00599
Homo sapiens HEK293 Potency 446.7 nM None
Homo sapiens HEK293 Potency 1834.9 nM None
Homo sapiens HeLa EC50 26100.0 nM 10.1016/j.bmcl.2017.08.045
Homo sapiens Histone deacetylase 6 IC50 731.9 nM 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 7.17 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 84.3 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 99.53 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 891.3 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 1412.5 nM None
Homo sapiens HL-60 GI50 24154.61 nM None
Homo sapiens HOP-92 GI50 15595.53 nM None
Homo sapiens Hs-578T GI50 22600.0 nM 10.1016/0960-894X(95)00046-V
Homo sapiens Hs-578T GI50 22646.44 nM None
Homo sapiens Huh-7 Activity nan None 10.1021/jm201328e
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 15848.9 nM None
Homo sapiens IGROV-1 GI50 19769.7 nM None
Homo sapiens K562 GI50 25176.77 nM None
Homo sapiens KM12 GI50 10000.0 nM None
Homo sapiens LS174T Activity 0.5 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 1.3 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 1.4 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 1.5 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 2.1 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 2.2 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 2.4 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 2.7 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 4.1 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 4.4 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 4.5 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 4.7 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 5.6 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 6.1 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 7.0 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 7.2 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 9.6 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 10.7 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 11.8 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 13.9 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 16.8 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 24.7 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 25.9 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 41.5 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 54.6 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 65.7 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 68.3 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 75.8 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 76.9 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 80.3 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 81.6 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 85.4 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 87.3 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 87.4 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity 89.5 % 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Activity nan None 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T IC50 6100.0 nM 10.1021/acs.jnatprod.2c00224
Homo sapiens LS174T Inhibition nan % 10.1021/acs.jnatprod.2c00224
Homo sapiens LXR-beta IC50 67574.0 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 28183.8 nM None
Homo sapiens M14 GI50 17100.15 nM None
Homo sapiens Malme-3M GI50 28840.32 nM None
Homo sapiens Matrix metalloproteinase 9 IC50 7.95 ug.mL-1 10.1016/j.bmcl.2006.09.042
Homo sapiens MDA-N GI50 15205.48 nM None
Homo sapiens MOLT-4 GI50 19860.95 nM None
Homo sapiens NCI/ADR-RES GI50 19453.6 nM None
Homo sapiens NCI-H23 GI50 17823.79 nM None
Homo sapiens Niemann-Pick C1 protein Potency 2909.3 nM None
Homo sapiens Niemann-Pick C1 protein Potency 5623.4 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 461.1 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 920.0 nM None
Homo sapiens OVCAR-4 GI50 18900.0 nM 10.1016/0960-894X(95)00046-V
Homo sapiens OVCAR-4 GI50 18923.44 nM None
Homo sapiens OVCAR-5 GI50 17418.07 nM None
Homo sapiens OVCAR-8 GI50 26181.83 nM None
Homo sapiens Parathyroid hormone receptor Potency 17782.8 nM None
Homo sapiens PC-3 GI50 22233.1 nM None
Homo sapiens Peripheral myelin protein 22 Potency 75686.3 nM None
Homo sapiens Phosphodiesterase 5A IC50 1230.0 nM 10.1016/j.bmcl.2020.127097
Homo sapiens Prelamin-A/C Potency 707.9 nM None
Homo sapiens Pyruvate kinase isozymes M1/M2 Potency 3162.3 nM None
Homo sapiens Ras-related protein Rab-9A Potency 1778.3 nM None
Homo sapiens Ras-related protein Rab-9A Potency 2909.3 nM None
Homo sapiens RKO IC50 50000.0 nM 10.1021/acs.jnatprod.2c00224
Homo sapiens RPMI-8226 GI50 15031.42 nM None
Homo sapiens RXF 393 GI50 18793.17 nM None
Homo sapiens Serine/threonine-protein kinase mTOR Potency 18492.7 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 100000.0 nM 10.1021/np960678l
Homo sapiens Serum albumin Ka 1.0 uM 10.1016/j.bmcl.2017.08.045
Homo sapiens SF-268 GI50 26791.68 nM None
Homo sapiens SF-295 GI50 14060.48 nM None
Homo sapiens SK-MEL-28 GI50 25176.77 nM None
Homo sapiens SK-MEL-5 GI50 14689.26 nM None
Homo sapiens SK-OV-3 GI50 19408.86 nM None
Homo sapiens SNB-19 GI50 15776.11 nM None
Homo sapiens SNB-75 GI50 18879.91 nM None
Homo sapiens SR GI50 24434.31 nM None
Homo sapiens Survival motor neuron protein Potency 7943.3 nM None
Homo sapiens SW480 IC50 50000.0 nM 10.1021/acs.jnatprod.2c00224
Homo sapiens SW-620 GI50 18578.04 nM None
Homo sapiens T47D GI50 15739.83 nM None
Homo sapiens TAR DNA-binding protein 43 Potency 3548.1 nM None
Homo sapiens Thrombopoietin Potency 316.2 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 12589.3 nM None
Homo sapiens TK-10 GI50 29580.12 nM None
Homo sapiens Transient receptor potential cation channel subfamily A member 1 Activity nan None 10.1021/acs.jnatprod.5b00599
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 2592.9 nM None
Homo sapiens U-251 GI50 15275.66 nM None
Homo sapiens UO-31 GI50 14893.61 nM None
Leishmania major 2,3-bisphosphoglycerate-independent phosphoglycerate mutase Potency 23934.1 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 12589.3 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 35481.3 nM None
Photinus pyralis Luciferin 4-monooxygenase Potency 952.8 nM None
Plasmodium falciparum Plasmodium falciparum IC50 10000.0 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum Potency 1471.6 nM None
Plasmodium falciparum Plasmodium falciparum Potency 1651.1 nM None
Plasmodium falciparum Plasmodium falciparum Potency 6573.3 nM None
Rattus norvegicus Aorta Activity 72.0 % 10.1021/np960161+
Rattus norvegicus Aorta Activity nan None 10.1021/np960161+
Rattus norvegicus Aorta EC50 29.7 nM 10.1016/j.ejmech.2019.02.037
Rattus norvegicus Aorta EC50 156.0 nM 10.1016/j.ejmech.2019.02.037
Rattus norvegicus Aorta EC50 1050.0 nM 10.1021/np960161+
Rattus norvegicus Aorta EC50 1330.0 nM 10.1016/j.bmc.2009.02.015
Rattus norvegicus Aorta EC50 1750.0 nM 10.1021/np960161+
Rattus norvegicus Aorta Emax 23.0 % 10.1021/np960161+
Rattus norvegicus Aorta Emax 66.3 % 10.1016/j.ejmech.2019.02.037
Rattus norvegicus Aorta Emax 75.3 % 10.1016/j.ejmech.2019.02.037
Rattus norvegicus Aorta Emax 79.3 % 10.1016/j.bmc.2009.02.015
Rattus norvegicus Aorta Emax 96.0 % 10.1021/np960161+
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 17782.8 nM None
Rattus norvegicus Rattus norvegicus Activity nan None 10.1016/j.ejmech.2019.02.037
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 28183.8 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 29934.9 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 39810.7 nM None
Rattus norvegicus Vanilloid receptor Activity -200.3 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -157.2 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -55.0 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity 0.0 mV 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity nan None 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor EC50 2060.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Inhibition nan % 10.1021/acs.jnatprod.5b00599
Saccharomyces cerevisiae Saccharomyces cerevisiae Potency 1636.0 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition -0.638 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -4.67 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.1 % 10.6019/CHEMBL4495565
Trypanosoma cruzi Cruzipain Potency 39810.7 nM None
None ADMET Activity nan None 10.1021/acs.jnatprod.2c00224
None ADMET IC50 3.0 nM 10.1016/s0960-894x(03)00469-4
None ADMET IC50 13.0 nM 10.1016/s0960-894x(03)00469-4
None NON-PROTEIN TARGET Potency 3.0 nM None
None NON-PROTEIN TARGET Potency 375.5 nM None
None NON-PROTEIN TARGET Potency 840.7 nM None
None NON-PROTEIN TARGET Potency 5951.8 nM None
None NON-PROTEIN TARGET Potency 12589.3 nM None
None NON-PROTEIN TARGET Potency 14125.4 nM None
None No relevant target Inhibition nan % 10.1016/j.ejmech.2019.05.055
None No relevant target solubility nan None 10.1016/j.bmcl.2017.08.045
None No relevant target Solubility 25.7 nM 10.1016/j.bmcl.2017.08.045
None No relevant target Solubility 27.1 nM 10.1016/j.bmcl.2017.08.045
None No relevant target Solubility 32.8 nM 10.1016/j.bmcl.2017.08.045
None No relevant target Solubility 33.0 nM 10.1016/j.bmcl.2017.08.045
None Nucleic Acid Activity 27.6 uM 10.1021/jm201328e
None Nucleic Acid Activity 1032.98 None 10.1021/jm201328e
None Unchecked AC50 25060.0 nM None
None Unchecked AC50 195000.0 nM None
None Unchecked Activity nan None 10.1021/acs.jnatprod.2c00224
None Unchecked Activity nan None 10.1021/np960161+
None Unchecked IC50 4300.0 nM 10.1021/acs.jnatprod.2c00224
None Unchecked IC50 67574.0 nM None
None Unchecked Inhibition nan % 10.1021/acs.jnatprod.2c00224
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Ka 1.0 uM 10.1016/j.bmcl.2017.08.045
None Unchecked Potency 22.4 nM None
None Unchecked Potency 446.7 nM None
None Unchecked Potency 730.8 nM None
None Unchecked Potency 819.9 nM None
None Unchecked Potency 1122.0 nM None
None Unchecked Potency 1157.7 nM None
None Unchecked Potency 4466.8 nM None
None Unchecked Potency 5011.9 nM None
None Unchecked Potency 5804.8 nM None
None Unchecked Potency 9200.0 nM None
None Unchecked Potency 10000.0 nM None
None Unchecked Potency 15848.9 nM None
None Unchecked Potency 16360.1 nM None
None Unchecked Potency 19952.6 nM None
None Unchecked Ratio IC50 nan None 10.1016/j.ejmech.2019.05.055

Metabolism Information