INTEGERRIMINE

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 Search

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-IKZAEVNJSA-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	335.3948
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19505372 | https://www.ncbi.nlm.nih.gov/pubmed/2492804

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 Target	Pharmacology	Condition	Potency
glutathione transferase activity 6 Target ID: GO:0004364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6533413	Inhibitor 8297
Trypanosoma brucei brucei 12 Target ID: CHEMBL612851 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19505372	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19505372	Primary		Basic research	Unknown Approved Use Unknown
Gastric ulcer 67 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15213731 https://www.ncbi.nlm.nih.gov/pubmed/15507358	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids.	2010 Mar 15	20092275
The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury.	2011 Feb 4	21126554
Metabolomic and genomic evidence for compromised bile acid homeostasis by senecionine, a hepatotoxic pyrrolizidine alkaloid.	2014 May 19	24641316
Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis.	2015 Oct	26100227

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:40:16 GMT 2023` Edited by `admin` on `Fri Dec 15 19:40:16 GMT 2023`
Record UNII	3179A6U4PN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INTEGERRIMINE

Common Name

English

NSC-79540

Code

English

(-)-INTEGERRIMINE

Common Name

English

SQUALIDIN

Common Name

English

SQUALIDINE

Common Name

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-, (3E,5R,6R,14AR,14BR)-

Systematic Name

English

SENECIONINE C15-TRANS ISOMER [MI]

Common Name

English

SENECIONAN-11,16-DIONE, 12-HYDROXY-, (15E)-

Common Name

English

Code System Code Type Description

CAS

480-79-5