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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H25NO5
Molecular Weight 335.3948
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SENECIONINE

SMILES

[H][C@]12CCN3CC=C(COC(=O)[C@](C)(O)[C@H](C)C\C(=C\C)C(=O)O1)[C@]23[H]

InChI

InChIKey=HKODIGSRFALUTA-JTLQZVBZSA-N
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

HIDE SMILES / InChI

Description

The pyrrolizidine alkaloid senecionine has been shown to produce an increase in cytosolic free Ca2+ concentration in isolated hepatocytes that correlated with an increase in cellular toxicity. Senecionine inhibits the sequestration of Ca2+ in extramitochondrial and mitochondrial compartments possibly by inactivating free sulfhydryl groups and oxidizing pyridine nucleotides respectively. Senecionine showed moderate antitrypanosomal activity with an IC50 value of 41.78 ug/ml.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Pharmacokinetic experiments of intravenous administration in the jugular-catheterized rat model: An aqueous solution contained senecionine was administered to rats intravenously at dose of 1.5 mg/kg. Pharmacokinetic experiments of oral administration in the jugular-catheterized rat model: An aqueous solution of senecionine was administered orally to rats by gavage at doses of 24, 12, and 6 mg/kg.
Route of Administration: Other
In Vitro Use Guide
Senecionine was cocultured for 2 hr with a NADPH-generating system and rat liver S9. Senecionine showed a dose-dependent inhibition of colony formation at 50, 100, and 300 uM and induction of megalocytosis at 500 uM.