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name Structure Reference Source Properties Activities Metabolism

Evodiamine; (±)-form

AlkaPlorer ID: AK014383

Synonym: None

IUPAC Name: 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)C21

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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

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InChIKey: TXDUTHBFYKGSAH-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

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
Electrophorus electricus Acetylcholinesterase IC50 10000.0 nM 10.1016/j.ejmech.2014.05.002
Electrophorus electricus Acetylcholinesterase Inhibition 37.0 % 10.1016/j.ejmech.2014.05.002
Equus caballus Cholinesterase IC50 4620.0 nM 10.1016/j.ejmech.2014.05.002
Equus caballus Cholinesterase Inhibition 5.34 % 10.1016/j.ejmech.2014.05.002
Homo sapiens A549 IC50 980.0 nM 10.1016/j.bmc.2016.05.001
Homo sapiens A549 IC50 77240.0 nM 10.1021/acs.jmedchem.1c01411
Homo sapiens Bel-7402 IC50 1190.0 nM 10.1016/j.ejmech.2018.04.009
Homo sapiens Caco-2 IC50 2730.0 nM 10.1016/j.ejmech.2018.04.009
Homo sapiens DNA topoisomerase I Inhibition 3.67 % 10.1021/acs.jmedchem.2c00520
Homo sapiens DNA topoisomerase I Inhibition 24.2 % 10.1016/j.ejmech.2022.114304
Homo sapiens DNA topoisomerase I Inhibition 63.41 % 10.1021/acs.jmedchem.2c00520
Homo sapiens DNA topoisomerase II alpha Inhibition 47.99 % 10.1021/acs.jmedchem.2c00520
Homo sapiens HCCLM9 IC50 9270.0 nM 10.1021/acs.jmedchem.2c00520
Homo sapiens HCT-116 IC50 32670.0 nM 10.1021/acs.jmedchem.1c01411
Homo sapiens HEK293 Activity nan None 10.1021/acs.jnatprod.5b00599
Homo sapiens HEK293 IC50 100000.0 nM 10.1021/acs.jmedchem.1c01411
Homo sapiens HepG2 IC50 2670.0 nM 10.1021/acs.jmedchem.2c00520
Homo sapiens HepG2 IC50 9320.0 nM 10.1016/j.bmcl.2017.10.014
Homo sapiens HepG2 Potency 35481.3 nM None
Homo sapiens Histone deacetylase 6 Inhibition 0.33 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 36.27 % 10.6019/CHEMBL4808148
Homo sapiens HL-60 IC50 1360.0 nM 10.1016/j.ejmech.2018.04.009
Homo sapiens HL-60 IC50 1390.0 nM 10.1016/j.bmcl.2017.10.014
Homo sapiens Huh-7 Activity 0.57 % 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 Activity 1.64 % 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 Activity 5.83 % 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 Activity 15.93 % 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 Activity 23.42 % 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 Activity 60.65 % 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 Activity 92.0 % 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 Activity nan None 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 IC50 2180.0 nM 10.1021/acs.jmedchem.2c00520
Homo sapiens Huh-7 TGI nan None 10.1021/acs.jmedchem.2c00520
Homo sapiens L02 IC50 3950.0 nM 10.1021/acs.jmedchem.2c00520
Homo sapiens MCF-10A IC50 100000.0 nM 10.1021/acs.jmedchem.1c01411
Homo sapiens MCF7 IC50 28530.0 nM 10.1016/j.ejmech.2018.04.009
Homo sapiens MDA-MB-231 IC50 13300.0 nM 10.1021/acs.jmedchem.1c01411
Homo sapiens MDA-MB-231 Inhibition 38.9 % 10.1021/acs.jmedchem.1c01411
Homo sapiens MDA-MB-231 Inhibition 53.3 % 10.1021/acs.jmedchem.1c01411
Homo sapiens MDA-MB-231 Inhibition 73.3 % 10.1021/acs.jmedchem.1c01411
Homo sapiens MDA-MB-435 IC50 6300.0 nM 10.1021/acs.jmedchem.1c01411
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 22387.2 nM None
Homo sapiens PBMC IC50 20960.0 nM 10.1016/j.ejmech.2018.04.009
Homo sapiens PBMC IC50 22870.0 nM 10.1016/j.bmcl.2017.10.014
Homo sapiens PC-3 IC50 13970.0 nM 10.1016/j.bmcl.2017.10.014
Homo sapiens Peroxisome proliferator-activated receptor gamma FC 0.49 None 10.1021/acs.jnatprod.1c00881
Homo sapiens Phosphodiesterase 5A IC50 2100.0 nM 10.1016/j.ejmech.2021.113815
Homo sapiens Phosphodiesterase 5A IC50 2100.0 nM 10.1021/acs.jmedchem.0c00983
Homo sapiens Phosphodiesterase 6C EC50 20000.0 nM 10.1021/acs.jmedchem.0c00983
Homo sapiens Retinoid X receptor alpha FC 1.04 None 10.1021/acs.jnatprod.1c00881
Homo sapiens SGC-7901 IC50 6930.0 nM 10.1016/j.ejmech.2018.04.009
Homo sapiens SK-HEP1 Activity 0.27 % 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 Activity 1.01 % 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 Activity 2.79 % 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 Activity 3.57 % 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 Activity 36.0 % 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 Activity 60.43 % 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 Activity 85.0 % 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 Activity nan None 10.1021/acs.jmedchem.2c00520
Homo sapiens SK-HEP1 IC50 2920.0 nM 10.1021/acs.jmedchem.2c00520
Homo sapiens SMMC-7721 IC50 3040.0 nM 10.1021/acs.jmedchem.2c00520
Homo sapiens THP-1 IC50 3370.0 nM 10.1016/j.bmcl.2017.10.014
Homo sapiens Transient receptor potential cation channel subfamily A member 1 Activity nan None 10.1021/acs.jnatprod.5b00599
Mus musculus Mus musculus Activity nan None 10.1021/acs.jnatprod.1c00881
Mus musculus Mus musculus FC 3.6 None 10.1021/acs.jnatprod.1c00881
Mus musculus Mus musculus Inhibition 33.2 % 10.1021/acs.jnatprod.1c00881
Mus musculus Mus musculus Inhibition 34.0 % 10.1021/acs.jnatprod.1c00881
Mus musculus Mus musculus Inhibition 42.3 % 10.1021/acs.jnatprod.1c00881
Mus musculus Mus musculus Inhibition 50.0 % 10.1021/acs.jnatprod.1c00881
Mus musculus Mus musculus Inhibition 65.1 % 10.1021/acs.jnatprod.1c00881
Mus musculus Mus musculus Inhibition 68.1 % 10.1021/acs.jnatprod.1c00881
Rattus norvegicus Vanilloid receptor Activity -2396.3 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -528.2 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -492.3 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -447.5 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -439.3 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -422.3 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -416.3 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -393.2 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -390.0 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -369.7 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -328.0 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -296.0 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -259.9 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -255.8 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -242.6 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -236.8 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -235.8 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -208.4 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -195.2 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -172.4 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -165.1 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -159.6 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -157.8 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -143.4 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -142.8 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -132.5 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -94.8 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -81.7 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -81.6 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -75.0 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -60.3 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -49.1 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -35.9 pA/pF 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Activity -6.4 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 100.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor EC50 180.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor EC50 330.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor EC50 600.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor EC50 860.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor EC50 2380.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor IC50 440.0 nM 10.1021/acs.jnatprod.5b00599
Rattus norvegicus Vanilloid receptor Inhibition nan % 10.1021/acs.jnatprod.5b00599
None ADMET Activity nan None 10.1021/acs.jmedchem.2c00520
None ADMET Activity nan None 10.1021/acs.jnatprod.1c00881
None ADMET IC50 340.0 nM 10.1016/j.bmc.2016.05.001
None ADMET Ratio 0.37 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 0.41 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 0.48 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 0.49 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 0.78 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 0.81 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 1.22 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 1.29 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 1.33 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 1.48 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 3.64 None 10.1021/acs.jnatprod.1c00881
None ADMET Ratio 3.85 None 10.1021/acs.jnatprod.1c00881
None ADMET Selectivity Index 10.7 None 10.1021/acs.jmedchem.1c01411
None NON-PROTEIN TARGET IC50 1160.0 nM 10.1016/j.bmc.2016.05.001
None NON-PROTEIN TARGET IC50 1230.0 nM 10.1016/j.bmc.2016.05.001
None NON-PROTEIN TARGET Potency 0.9 nM None
None NON-PROTEIN TARGET Potency 18.8 nM None
None NON-PROTEIN TARGET Potency 1677.4 nM None
None NON-PROTEIN TARGET Potency 9432.9 nM None
None Unchecked Activity 0.27 % 10.1021/acs.jmedchem.2c00520
None Unchecked Activity 0.9 % 10.1021/acs.jmedchem.2c00520
None Unchecked Activity 4.44 % 10.1021/acs.jmedchem.2c00520
None Unchecked Activity 94.4 % 10.1021/acs.jmedchem.2c00520
None Unchecked Activity nan None 10.1021/acs.jmedchem.2c00520
None Unchecked FC 1.53 None 10.1021/acs.jnatprod.1c00881
None Unchecked Inhibition nan % 10.1021/acs.jnatprod.1c00881
None Unchecked Ratio IC50 2.16 None 10.1016/j.ejmech.2014.05.002

Metabolism Information