Riddelliine (BioDeep_00000395559)

 

Secondary id: BioDeep_00000008056

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(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*))-

化学式: C18H23NO6 (349.1525298)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.89%

分子结构信息

SMILES: C=C1C/C(=C/C)C(=O)O[C@@H]2CCN3CC=C(COC(=O)[C@@]1(O)CO)[C@H]23
InChI: 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

描述信息

Riddelline is a colorless to off-white crystalline solid. Starts turning brown at approximately 329 °F; is blackish-brown at melting point. (NTP, 1992)
Riddelliine is a macrodiolide that is 13,19-didehydrosenecionan bearing two additional hydroxy substituents at positions 12 and 18 as well as two additional oxo groups at positions 11 and 16. It has a role as a genotoxin, a mutagen and a carcinogenic agent. It is a pyrrolizine alkaloid, an organic heterotricyclic compound, an olefinic compound and a macrodiolide. It is functionally related to a senecionan.
Riddelliine is a natural product found in Senecio aegyptius, Senecio glaucus, and other organisms with data available.
A macrodiolide that is 13,19-didehydrosenecionan bearing two additional hydroxy substituents at positions 12 and 18 as well as two additional oxo groups at positions 11 and 16.

同义名列表

21 个代谢物同义名

(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*))-; (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)-; (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)-; [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)-; (6S,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methylene-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione; (1R,4Z,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione; (15Z)-12,18-dihydroxy-13,19-didehydrosenecionan-11,16-dione; (Z)-ethylidene-hydroxy-(hydroxymethyl)-methylene-[?]dione; Senecionan-11,16-dione, 13,19-didehydro-12,18-dihydroxy-; 13,19-Didehydro-12,18-dihydroxysenecionan-11,16-dione; 18-Hydroxyseneciphylline; RIDDELLINE [HSDB]; UNII-81YO8GX9J8; riddelliine; Riddelline; 81YO8GX9J8; Riddeliine; Riddeliin; 1ST164452; Riddeline; Riddelline



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

33 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Yueyang Pan, Jiang Ma, Hui Zhao, Peter P Fu, Ge Lin. Hepatotoxicity screening and ranking of structurally different pyrrolizidine alkaloids in zebrafish. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Jun; 178(?):113903. doi: 10.1016/j.fct.2023.113903. [PMID: 37390955]
  • Naji Said Aboud Hadi, Ezgi Eyluel Bankoglu, Helga Stopper. Genotoxicity of pyrrolizidine alkaloids in metabolically inactive human cervical cancer HeLa cells co-cultured with human hepatoma HepG2 cells. Archives of toxicology. 2023 01; 97(1):295-306. doi: 10.1007/s00204-022-03394-z. [PMID: 36273350]
  • Sara Abdelfatah, Janine Naß, Caroline Knorz, Sabine M Klauck, Jan-Heiner Küpper, Thomas Efferth. Pyrrolizidine alkaloids cause cell cycle and DNA damage repair defects as analyzed by transcriptomics in cytochrome P450 3A4-overexpressing HepG2 clone 9 cells. Cell biology and toxicology. 2022 04; 38(2):325-345. doi: 10.1007/s10565-021-09599-9. [PMID: 33884520]
  • Frances Widjaja, Sebastiaan Wesseling, Ivonne M C M Rietjens. Physiologically based kinetic modelling predicts the in vivo relative potency of riddelliine N-oxide compared to riddelliine in rat to be dose dependent. Archives of toxicology. 2022 01; 96(1):135-151. doi: 10.1007/s00204-021-03179-w. [PMID: 34669010]
  • Lukas Rutz, Lan Gao, Jan-Heiner Küpper, Dieter Schrenk. Structure-dependent genotoxic potencies of selected pyrrolizidine alkaloids in metabolically competent HepG2 cells. Archives of toxicology. 2020 12; 94(12):4159-4172. doi: 10.1007/s00204-020-02895-z. [PMID: 32910235]
  • Suparmi Suparmi, Sebastiaan Wesseling, Ivonne M C M Rietjens. Monocrotaline-induced liver toxicity in rat predicted by a combined in vitro physiologically based kinetic modeling approach. Archives of toxicology. 2020 09; 94(9):3281-3295. doi: 10.1007/s00204-020-02798-z. [PMID: 32518961]
  • Ammon W Brown, Bryan L Stegelmeier, Steven M Colegate, Kip E Panter, Edward L Knoppel, Jeffery O Hall. Heterozygous p53 knockout mouse model for dehydropyrrolizidine alkaloid-induced carcinogenesis. Journal of applied toxicology : JAT. 2015 Dec; 35(12):1557-63. doi: 10.1002/jat.3120. [PMID: 25690669]
  • Reuel A Field, Bryan L Stegelmeier, Steven M Colegate, Ammon W Brown, Benedict T Green. An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. Toxicon : official journal of the International Society on Toxinology. 2015 Apr; 97(?):36-45. doi: 10.1016/j.toxicon.2015.02.001. [PMID: 25666399]
  • Tao Chen, Zhiguang Li, Jian Yan, Xi Yang, William Salminen. MicroRNA expression profiles distinguish the carcinogenic effects of riddelliine in rat liver. Mutagenesis. 2012 Jan; 27(1):59-66. doi: 10.1093/mutage/ger060. [PMID: 21976715]
  • Ligia Verónica Hernández, Sergio Gonzalo, Marta Castro, María Pilar Arruebo, Miguel Angel Plaza, María Divina Murillo, Laura Grasa. Nuclear factor κB is a key transcription factor in the duodenal contractility alterations induced by lipopolysaccharide. Experimental physiology. 2011 Nov; 96(11):1151-62. doi: 10.1113/expphysiol.2011.060830. [PMID: 21890516]
  • Lei Guo, Nan Mei, Stacey Dial, James Fuscoe, Tao Chen. Comparison of gene expression profiles altered by comfrey and riddelliine in rat liver. BMC bioinformatics. 2007 Nov; 8 Suppl 7(?):S22. doi: 10.1186/1471-2105-8-s7-s22. [PMID: 18047722]
  • Nan Mei, Lei Guo, Ruqing Liu, James C Fuscoe, Tao Chen. Gene expression changes induced by the tumorigenic pyrrolizidine alkaloid riddelliine in liver of Big Blue rats. BMC bioinformatics. 2007 Nov; 8 Suppl 7(?):S4. doi: 10.1186/1471-2105-8-s7-s4. [PMID: 18047727]
  • Po C Chan, Joseph K Haseman, J D Prejean, Abraham Nyska. Toxicity and carcinogenicity of riddelliine in rats and mice. Toxicology letters. 2003 Oct; 144(3):295-311. doi: 10.1016/s0378-4274(03)00240-6. [PMID: 12927348]
  • NULL. Toxicology and carcinogenesis studies of riddelliine (CAS No. 23246-96-0) in F344/N rats and B6C3F1 mice (gavage studies). National Toxicology Program technical report series. 2003 May; ?(508):1-280. doi: NULL. [PMID: 12844193]
  • Abraham Nyska, Cindy R Moomaw, Julie F Foley, Robert R Maronpot, David E Malarkey, Connie A Cummings, Shyamal Peddada, Carolyn F Moyer, David G Allen, Greg Travlos, Po C Chan. The hepatic endothelial carcinogen riddelliine induces endothelial apoptosis, mitosis, S phase, and p53 and hepatocytic vascular endothelial growth factor expression after short-term exposure. Toxicology and applied pharmacology. 2002 Nov; 184(3):153-64. doi: 10.1006/taap.2002.9485. [PMID: 12460743]
  • Lee Williams, Ming W Chou, Jian Yan, John F Young, Po C Chan, Daniel R Doerge. Toxicokinetics of riddelliine, a carcinogenic pyrrolizidine alkaloid, and metabolites in rats and mice. Toxicology and applied pharmacology. 2002 Jul; 182(2):98-104. doi: 10.1006/taap.2002.9441. [PMID: 12140173]
  • S T Lee, T K Schoch, B L Stegelmeier, D R Gardner, K A Than, R J Molyneux. Development of enzyme-linked immunosorbent assays for the hepatotoxic alkaloids riddelliine and riddelliine N-oxide. Journal of agricultural and food chemistry. 2001 Aug; 49(8):4144-51. doi: 10.1021/jf010042m. [PMID: 11513723]
  • T K Schoch, D R Gardner, B L Stegelmeier. GC/MS/MS detection of pyrrolic metabolites in animals poisoned with the pyrrolizidine alkaloid riddelliine. Journal of natural toxins. 2000 May; 9(2):197-206. doi: ". [PMID: 10868345]
  • Po Chan. NTP technical report on the toxicity studies of Riddelliine (CAS No. 23246-96-0) Administered by Gavage to F344 Rats and B6C3F1 Mice. Toxicity report series. 1993 Dec; 27(?):1-D9. doi: NULL. [PMID: 12209179]
  • R J Molyneux, A E Johnson, J D Olsen, D C Baker. Toxicity of pyrrolizidine alkaloids from Riddell groundsel (Senecio riddellii) to cattle. American journal of veterinary research. 1991 Jan; 52(1):146-51. doi: NULL. [PMID: 2021243]