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130-01-8,MFCD00221720
Catalog No.:AA000TS4

130-01-8 | [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-, (3Z,5R,6R,14aR,14bR)-

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1mg
≥98%
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$70.00   $49.00
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5mg
≥98%
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$240.00   $168.00
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10mg
≥98%
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$340.00   $238.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA000TS4
Chemical Name:
[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-, (3Z,5R,6R,14aR,14bR)-
CAS Number:
130-01-8
Molecular Formula:
C18H25NO5
Molecular Weight:
335.3948
MDL Number:
MFCD00221720
SMILES:
C/C=C\1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
NSC Number:
89935
Properties
Computed Properties
 
Complexity:
611  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
1  
XLogP3:
1.1  

Literature

Title: Structure-dependent induction of apoptosis by hepatotoxic pyrrolizidine alkaloids in the human hepatoma cell line HepaRG: Single versus repeated exposure.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20180401

Title: Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20151001

Title: Metabolomic and genomic evidence for compromised bile acid homeostasis by senecionine, a hepatotoxic pyrrolizidine alkaloid.

Journal: Chemical research in toxicology 20140519

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Haematological and immunological effects of repeated dose exposure of rats to integerrimine N-oxide from Senecio brasiliensis.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110901

Title: The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS.

Journal: Analytical and bioanalytical chemistry 20110701

Title: [Simultaneous quantitation of adonifoline and senecionine in Senecio herbs by UPLC-MS].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110301

Title: The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury.

Journal: Toxicology 20110204

Title: Identification of the UDP-glucuronosyltransferase isozyme involved in senecionine glucuronidation in human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100401

Title: Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids.

Journal: Chemical research in toxicology 20100315

Title: Pyrrolizidine alkaloids in pollen and pollen products.

Journal: Molecular nutrition & food research 20100201

Title: Simultaneous determination of senecionine, adonifoline and their metabolites in rat serum by UPLC-ESIMS and its application in pharmacokinetic studies.

Journal: Journal of pharmaceutical and biomedical analysis 20091205

Title: Feeding deterrence and detrimental effects of pyrrolizidine alkaloids fed to honey bees (Apis mellifera).

Journal: Journal of chemical ecology 20090901

Title: Determination of senkirkine and senecionine in Tussilago farfara using microwave-assisted extraction and pressurized hot water extraction with liquid chromatography tandem mass spectrometry.

Journal: Talanta 20090715

Title: The toxicity of Senecio inaequidens DC.

Journal: Journal of the South African Veterinary Association 20070901

Title: Modeling K(m) values using electrotopological state: substrates for cytochrome P450 3A4-mediated metabolism.

Journal: Bioorganic & medicinal chemistry letters 20050915

Title: Comparison of hepatic in vitro metabolism of the pyrrolizidine alkaloid senecionine in sheep and cattle.

Journal: American journal of veterinary research 20041101

Title: Differential metabolism of the pyrrolizidine alkaloid, senecionine, in Fischer 344 and Sprague-Dawley rats.

Journal: Archives of pharmacal research 20040501

Title: Variation in pyrrolizidine alkaloid patterns of Senecio jacobaea.

Journal: Phytochemistry 20040401

Title: Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants.

Journal: Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20030801

Title: Interplant alkaloid variation and Senecio vernalis toxicity in cattle.

Journal: Veterinary and human toxicology 20010601

Title: Defensive chemistry of Senecio miser.

Journal: Journal of natural products 20010101

Title: Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.

Journal: Journal of natural products 19910101

Title: Wang C, et al. The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. Anal Bioanal Chem. 2011 Jul;401(1):275-87.

Title: Kakrani HK, et al. Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats. J Ethnopharmacol. 1984 Dec;12(3):271-8.

Title: Tu ZB, et al. Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris. J Pharm Sci. 1988 May;77(5):461-3.

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SDS
Tags:130-01-8 Molecular Formula|130-01-8 MDL|130-01-8 SMILES|130-01-8 [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-, (3Z,5R,6R,14aR,14bR)-