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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H25NO5
Molecular Weight 335.3955
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SENECIONINE

SMILES

C/C(/[H])=C\1/C[C@@]([H])(C)[C@](C)(C(=O)OCC2=CCN3CC[C@]([H])([C@@]23[H])OC1=O)O

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

Molecular Formula C18H25NO5
Molecular Weight 335.3955
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids.
2010 Mar 15
The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury.
2011 Feb 4
Metabolomic and genomic evidence for compromised bile acid homeostasis by senecionine, a hepatotoxic pyrrolizidine alkaloid.
2014 May 19
Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis.
2015 Oct
Patents

Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:53:38 UTC 2021
Edited
by admin
on Sat Jun 26 11:53:38 UTC 2021
Record UNII
BO6N1U5YG6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SENECIONINE
MI  
Common Name English
(-)-SENECIONINE
Common Name English
SENECIONIN
Common Name English
AUREINE
Common Name English
NSC-89935
Code English
(1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE, 3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-5,6-DIMETHYL-, (3Z,5R,6R,14AR,14BR)-
Systematic Name English
SENECIONINE [MI]
Common Name English
Code System Code Type Description
FDA UNII
BO6N1U5YG6
Created by admin on Sat Jun 26 11:53:38 UTC 2021 , Edited by admin on Sat Jun 26 11:53:38 UTC 2021
PRIMARY
CAS
130-01-8
Created by admin on Sat Jun 26 11:53:38 UTC 2021 , Edited by admin on Sat Jun 26 11:53:38 UTC 2021
PRIMARY
HSDB
3535
Created by admin on Sat Jun 26 11:53:38 UTC 2021 , Edited by admin on Sat Jun 26 11:53:38 UTC 2021
PRIMARY
MERCK INDEX
M9860
Created by admin on Sat Jun 26 11:53:38 UTC 2021 , Edited by admin on Sat Jun 26 11:53:38 UTC 2021
PRIMARY Merck Index
PUBCHEM
5280906
Created by admin on Sat Jun 26 11:53:38 UTC 2021 , Edited by admin on Sat Jun 26 11:53:38 UTC 2021
PRIMARY
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