RIDDELLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23NO6
Molecular Weight	349.3783
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SVCNNZDUGWLODJ-RAYFHMIRSA-N

InChI=1S/C18H23NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,14-15,20,23H,2,5-10H2,1H3/b12-3-/t14-,15-,18-/m1/s1

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Transformation of BALB/c-3T3 cells: IV. Rank-ordered potency of 24 chemical responses detected in a sensitive new assay procedure.	1993 Jul	8243401
Toxicity and carcinogenicity of riddelliine following 13 weeks of treatment to rats and mice.	1994 Aug	7985194
Toxicokinetics of riddelliine, a carcinogenic pyrrolizidine alkaloid, and metabolites in rats and mice.	2002 Jul 15	12140173
Toxicity and carcinogenicity of riddelliine in rats and mice.	2003 Oct 15	12927348
Chemical-specific alterations in ras, p53, and beta-catenin genes in hemangiosarcomas from B6C3F1 mice exposed to o-nitrotoluene or riddelliine for 2 years.	2003 Sep 15	13678655
Analysis of vascular endothelial growth factor (VEGF) and a receptor subtype (KDR/flk-1) in the liver of rats exposed to riddelliine: a potential role in the development of hemangiosarcoma.	2004 Jul	15384251
Gene expression changes induced by the tumorigenic pyrrolizidine alkaloid riddelliine in liver of Big Blue rats.	2007 Nov 1	18047727
Comparison of gene expression profiles altered by comfrey and riddelliine in rat liver.	2007 Nov 1	18047722
Final report on carcinogens background document for riddelliine.	2008 Aug	20737008
Nuclear factor κB is a key transcription factor in the duodenal contractility alterations induced by lipopolysaccharide.	2011 Nov	21890516

Name

Type

Language

RIDDELLINE

Common Name

English

SENECIONAN-11,16-DIONE, 13,19-DIDEHYDRO-12,18-DIHYDROXY-

Systematic 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-6- (HYDROXYMETHYL)-5-METHYLENE-, (3Z,6S,14AR,14BR)-

Systematic Name

English

RIDDELIIN

Common Name

English

13,19-DIDEHYDRO-12,18-DIHYDROXYSENECIONAN-11,16-DIONE

Systematic 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-6-(HYDROXYMETHYL)-5-METHYLENE-, (6S-(3Z,6R*,14AS*,14BS*))-

Systematic Name

English

RIDDELLINE [HSDB]

Common Name

English

RIDDELINE

Common Name

English

Code System Code Type Description

WIKIPEDIA

Riddelline