U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11NO2
Molecular Weight 153.1784
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEHYDROHELIOTRIDINE

SMILES

OCC1=C2[C@@H](O)CCN2C=C1

InChI

InChIKey=QFPRRXUPCPFWKD-ZETCQYMHSA-N
InChI=1S/C8H11NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,3,7,10-11H,2,4-5H2/t7-/m0/s1

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Riddelliine N-oxide is a phytochemical and mammalian metabolite with genotoxic activity that is comparable to the parent pyrrolizidine alkaloid riddelliine.
2003 Dec 10
Human liver microsomal metabolism and DNA adduct formation of the tumorigenic pyrrolizidine alkaloid, riddelliine.
2003 Jan
Identification of DNA adducts derived from riddelliine, a carcinogenic pyrrolizidine alkaloid.
2003 Sep
Differential metabolism of the pyrrolizidine alkaloid, senecionine, in Fischer 344 and Sprague-Dawley rats.
2004 May
Metabolic formation of DHP-derived DNA adducts from a representative otonecine type pyrrolizidine alkaloid clivorine and the extract of Ligularia hodgsonnii hook.
2004 May
Comparison of hepatic in vitro metabolism of the pyrrolizidine alkaloid senecionine in sheep and cattle.
2004 Nov
Metabolic activation of the tumorigenic pyrrolizidine alkaloid, monocrotaline, leading to DNA adduct formation in vivo.
2005 Aug 8
Human liver microsomal reduction of pyrrolizidine alkaloid N-oxides to form the corresponding carcinogenic parent alkaloid.
2005 Mar 15
Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, lasiocarpine.
2006 Jan 8
Formation of DHP-derived DNA adducts in vivo from dietary supplements and chinese herbal plant extracts containing carcinogenic pyrrolizidine alkaloids.
2006 Sep
Metabolic activation of retronecine and retronecine N-oxide - formation of DHP-derived DNA adducts.
2008 Apr
Final report on carcinogens background document for riddelliine.
2008 Aug
Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine.
2008 May 5
Comfrey (Symphytum Officinale. l.) and Experimental Hepatic Carcinogenesis: A Short-term Carcinogenesis Model Study.
2010 Jun
High-performance liquid chromatography electrospray ionization tandem mass spectrometry for the detection and quantitation of pyrrolizidine alkaloid-derived DNA adducts in vitro and in vivo.
2010 Mar 15
Metabolism, genotoxicity, and carcinogenicity of comfrey.
2010 Oct
Name Type Language
DEHYDROHELIOTRIDINE
Common Name English
HELIOTRIDINE, 3,8-DIDEHYDRO-
Common Name English
1H-PYRROLIZINE-7-METHANOL, 2,3-DIHYDRO-1-HYDROXY-, (1S)-
Systematic Name English
3,8-DEHYDROHELIOTRIDINE
Common Name English
NSC-116336
Code English
(+)-DEHYDROHELIOTRIDINE
Common Name English
Code System Code Type Description
NSC
116336
Created by admin on Sat Dec 16 09:44:09 GMT 2023 , Edited by admin on Sat Dec 16 09:44:09 GMT 2023
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HSDB
3480
Created by admin on Sat Dec 16 09:44:09 GMT 2023 , Edited by admin on Sat Dec 16 09:44:09 GMT 2023
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EPA CompTox
DTXSID00181000
Created by admin on Sat Dec 16 09:44:09 GMT 2023 , Edited by admin on Sat Dec 16 09:44:09 GMT 2023
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PUBCHEM
272106
Created by admin on Sat Dec 16 09:44:09 GMT 2023 , Edited by admin on Sat Dec 16 09:44:09 GMT 2023
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FDA UNII
EGL727L56R
Created by admin on Sat Dec 16 09:44:09 GMT 2023 , Edited by admin on Sat Dec 16 09:44:09 GMT 2023
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CAS
26400-24-8
Created by admin on Sat Dec 16 09:44:09 GMT 2023 , Edited by admin on Sat Dec 16 09:44:09 GMT 2023
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