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Evodiamine

AlkaPlorer ID: AK000626

Synonym: '', 'Evodiamine'

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

Structure

SMILES: CN1C2=CC=CC=C2C(=O)N2CCC3=C(NC4=CC=CC=C34)[C@H]21

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InChI: InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1

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InChIKey: TXDUTHBFYKGSAH-SFHVURJKSA-N

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Reference

MINOR ALKALOIDS OF<i>ARALIOPSIS TABOUENSIS</i>

PubChem CID: 442088

CAS: 518-17-2

LOTUS: LTS0199197

NPASS: NPC141612

data_source: manually

Properties Information

Molecule Weight: 303.365

TPSA？: 39.34

MolLogP？: 3.3148000000000017

Number of H-Donors: 1

Number of H-Acceptors: 2

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens A549 IC50 200000.0 nM 10.1021/acs.jmedchem.9b01626
Homo sapiens DNA topoisomerase I Inhibition nan % 10.1016/j.bmc.2013.09.030
Homo sapiens HCT-116 IC50 200000.0 nM 10.1021/acs.jmedchem.9b01626
Homo sapiens HepG2 Inhibition 69.0 % 10.1016/j.bmc.2013.09.030
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Inhibition nan % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 8.1 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 9.0 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 11.9 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 16.8 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 27.6 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 33.2 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 39.3 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 41.9 % 10.1039/C6MD00170J
Homo sapiens MCF7 Activity 51.5 % 10.1039/C6MD00170J
Homo sapiens MCF7 IC50 5400.0 nM 10.1039/C6MD00170J
Homo sapiens MCF7 Inhibition 44.0 % 10.1016/j.bmc.2013.09.030
Homo sapiens MDA-MB-435 IC50 22100.0 nM 10.1021/acs.jmedchem.9b01626
Homo sapiens MSTO-211H IC50 540.0 nM 10.1039/C6MD00170J
Homo sapiens NAD-dependent deacetylase sirtuin 1 Inhibition 4.2 % 10.1016/j.bmc.2013.09.030
Homo sapiens NAD-dependent deacetylase sirtuin 2 Inhibition 71.0 % 10.1016/j.bmc.2013.09.030
Homo sapiens NAD-dependent deacetylase sirtuin 3 Inhibition 20.0 % 10.1016/j.bmc.2013.09.030
Homo sapiens Phosphodiesterase 5A IC50 1300.0 nM 10.1021/acs.jmedchem.0c00983
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition -1.656 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -4.75 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 1.0 % 10.6019/CHEMBL4495565
None NON-PROTEIN TARGET IC50 260.0 nM 10.1039/C6MD00170J
None NON-PROTEIN TARGET IC50 2600.0 nM 10.1016/j.bmc.2013.09.030
None NON-PROTEIN TARGET Survival 26.75 % 10.1039/C6MD00170J
None NON-PROTEIN TARGET Survival 43.09 % 10.1039/C6MD00170J
None NON-PROTEIN TARGET Survival 53.22 % 10.1039/C6MD00170J
None NON-PROTEIN TARGET Survival 65.47 % 10.1039/C6MD00170J
None Unchecked IC50 19550.0 nM 10.1016/j.bmcl.2021.127954
None Unchecked IC50 48980.0 nM 10.1016/j.bmcl.2021.127954
None Unchecked IC50 100000.0 nM 10.1016/j.bmcl.2021.127954
None Unchecked Inhibition 60.0 % 10.1039/C6MD00170J
None Unchecked Inhibition 100.0 % 10.1039/C6MD00170J
None Unchecked Inhibition nan % 10.1039/C6MD00170J
None Unchecked Tm 75.5 degrees C 10.1039/C6MD00170J

Metabolism Information