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Senecionine

AlkaPlorer ID: AK010783

Synonym: None

IUPAC Name: (1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

Structure

SMILES: C/C=C1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

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InChI: InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1

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InChIKey: HKODIGSRFALUTA-JTLQZVBZSA-N

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Reference

PubChem CID: 5280906

CAS: 130-01-8

LOTUS: LTS0172395

SuperNatural Ⅲ: SN0128182-08

NPASS: NPC193471

Source

Species Genus Family Order Class Phylum Kingdom Domain
Fordia cauliflora Fordia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Acinetobacter genospecies Acinetobacter Moraxellaceae Moraxellales Gammaproteobacteria Pseudomonadota None Bacteria
Sagotia racemosa Sagotia Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Schizogyne glaberrima Schizogyne Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rhodomyrtus macrocarpa Rhodomyrtus Myrtaceae Myrtales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ficus erecta Ficus Moraceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tussilago farfara Tussilago Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pycnanthemum muticum Pycnanthemum Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Magnolia compressa Magnolia Magnoliaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Senecio scandens Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pityrogramma sulphurea Pityrogramma Pteridaceae Polypodiales Polypodiopsida Streptophyta Viridiplantae Eukaryota
Pteraster tesselatus Pteraster Pterasteridae Velatida Asteroidea Echinodermata Metazoa Eukaryota
None Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Anticarsia gemmatalis Anticarsia Erebidae Lepidoptera Insecta Arthropoda Metazoa Eukaryota
Carlina corymbosa Carlina Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 335.40000000000003

TPSA？: 76.07

MolLogP？: 1.1928

Number of H-Donors: 1

Number of H-Acceptors: 6

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cricetulus griseus CHO EC50 100.0 ug.mL-1 10.1016/jbse.2007.08.015
Electrophorus electricus Acetylcholinesterase Inhibition 7.46 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 19.16 % 10.1016/j.bmc.2012.09.040
Homo sapiens A204 IC50 150.0 ug.mL-1 10.1021/np50058a005
Homo sapiens ATP-dependent DNA helicase Q1 Potency 28183.8 nM None
Homo sapiens Cytochrome P450 3A4 Log 1/Km -2.477 None 10.1016/j.bmcl.2005.06.015
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 35481.3 nM None
Homo sapiens DNA polymerase iota Potency 100000.0 nM None
Homo sapiens DNA polymerase kappa Potency 89125.1 nM None
Homo sapiens Flap endonuclease 1 Potency 100000.0 nM None
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 39810.7 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Lactuca sativa Lactuca sativa Inhibition 50.0 % 10.1016/jbse.2007.08.015
Leptinotarsa decemlineata Leptinotarsa decemlineata EC50 1.3 microg/cm2 10.1016/jbse.2007.08.015
Myzus persicae Myzus persicae Activity 40.0 % 10.1016/jbse.2007.08.015
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 25118.9 nM None
Rhopalosiphum padi Rhopalosiphum padi Activity 40.0 % 10.1016/jbse.2007.08.015
Spodoptera littoralis Spodoptera littoralis Activity 84.0 % 10.1016/jbse.2007.08.015
Spodoptera littoralis Spodoptera littoralis EC50 50.0 microg/cm2 10.1016/jbse.2007.08.015
None ADMET EC50 100.0 ug.mL-1 10.1016/jbse.2007.08.015

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001547 C/C=C1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>C/C=C1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CC[N+]3([C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O)CC[C@@H](OC1=O)[C@@H]23 enzymemap_34968
AKRT001548 C/C=C1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23>>C/C=C1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CC[N+]3(O)CC[C@@H](OC1=O)[C@@H]23 R07373