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Chelidonine

AlkaPlorer ID: AK000873

Synonym: None

IUPAC Name: (1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

Structure

SMILES: CN1CC2=C3OCOC3=CC=C2[C@@H]2[C@H]1C1=CC3=C(C=C1C[C@@H]2O)OCO3

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InChI: InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1

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InChIKey: GHKISGDRQRSCII-ZOCIIQOWSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Chelidonium majus Chelidonium Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 353.37400000000014

TPSA？: 60.390000000000015

MolLogP？: 2.3313

Number of H-Donors: 1

Number of H-Acceptors: 6

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Electrophorus electricus Acetylcholinesterase Inhibition 29.78 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 6.72 % 10.1016/j.bmc.2012.09.040
Homo sapiens HCT-116 IC50 40000.0 nM 10.1016/j.bmcl.2019.126913
Homo sapiens HepG2 IC50 40000.0 nM 10.1016/j.bmcl.2019.126913
Homo sapiens HL-60 IC50 2200.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens Jurkat IC50 2200.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens K562 IC50 17650.0 nM 10.1016/j.bmcl.2019.126913
Homo sapiens L02 IC50 40000.0 nM 10.1016/j.bmcl.2019.126913
Homo sapiens MCF7 IC50 40000.0 nM 10.1016/j.bmcl.2019.126913
Homo sapiens MOLT-4 IC50 2200.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens PBMC IC50 40000.0 nM 10.1016/j.bmcl.2019.126913
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Mus musculus RAW264.7 Activity nan None 10.1016/j.bmcl.2011.09.128
Mus musculus RAW264.7 IC50 7300.0 nM 10.1016/j.bmcl.2011.09.128
Mus musculus RAW264.7 Inhibition nan % 10.1016/j.bmcl.2011.09.128

Metabolism Information