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
Toxicity of pyrrolizidine alkaloids from Riddell groundsel (Senecio riddellii) to cattle.	1991 Jan	2021243
NTP technical report on the toxicity studies of Riddelliine (CAS No. 23246-96-0) Administered by Gavage to F344 Rats and B6C3F1 Mice.	1993 Dec	12209179
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
The hepatic endothelial carcinogen riddelliine induces endothelial apoptosis, mitosis, S phase, and p53 and hepatocytic vascular endothelial growth factor expression after short-term exposure.	2002 Nov 1	12460743
Toxicology and carcinogenesis studies of riddelliine (CAS No. 23246-96-0) in F344/N rats and B6C3F1 mice (gavage studies).	2003 May	12844193
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
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