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

C\C=C1\CC(=C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

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

Molecular Formula	C18H23NO6
Molecular Weight	349.3783
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Nuclear factor κB is a key transcription factor in the duodenal contractility alterations induced by lipopolysaccharide.	2011-11	21890516
Final report on carcinogens background document for riddelliine.	2008-08	20737008
Gene expression changes induced by the tumorigenic pyrrolizidine alkaloid riddelliine in liver of Big Blue rats.	2007-11-01	18047727
Comparison of gene expression profiles altered by comfrey and riddelliine in rat liver.	2007-11-01	18047722
Differential mutagenicity of riddelliine in liver endothelial and parenchymal cells of transgenic big blue rats.	2004-11-25	15488633
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.	2004-07	15384251
Correlation of DNA adduct formation and riddelliine-induced liver tumorigenesis in F344 rats and B6C3F1 mice [Cancer Lett. 193 (2003) 119-125.	2004-04-15	15127726
Toxicity and carcinogenicity of riddelliine in rats and mice.	2003-10-15	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.	2003-09-15	13678655
Toxicology and carcinogenesis studies of riddelliine (CAS No. 23246-96-0) in F344/N rats and B6C3F1 mice (gavage studies).	2003-05	12844193
The hepatic endothelial carcinogen riddelliine induces endothelial apoptosis, mitosis, S phase, and p53 and hepatocytic vascular endothelial growth factor expression after short-term exposure.	2002-11-01	12460743
Toxicokinetics of riddelliine, a carcinogenic pyrrolizidine alkaloid, and metabolites in rats and mice.	2002-07-15	12140173
Toxicity and carcinogenicity of riddelliine following 13 weeks of treatment to rats and mice.	1994-08	7985194
NTP technical report on the toxicity studies of Riddelliine (CAS No. 23246-96-0) Administered by Gavage to F344 Rats and B6C3F1 Mice.	1993-12	12209179
Transformation of BALB/c-3T3 cells: IV. Rank-ordered potency of 24 chemical responses detected in a sensitive new assay procedure.	1993-07	8243401
Toxicity of pyrrolizidine alkaloids from Riddell groundsel (Senecio riddellii) to cattle.	1991-01	2021243

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:20:53 GMT 2025` Edited by `admin` on `Mon Mar 31 22:20:53 GMT 2025`
Record UNII	81YO8GX9J8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIDDELIIN

Preferred Name

English

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

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