Retronecine (BioDeep_00000001045)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


InChI=1/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s

化学式: C8H13NO2 (155.0946)
中文名称: 1H-吡咯里嗪-7-甲醇，2,3,5,7a-四氢-1-羟基-（1S-顺式）
谱图信息: 最多检出来源 Homo sapiens(feces) 43.22%

分子结构信息

SMILES: C1=C(CO)[C@@H]2[C@@H](CCN2C1)O
InChI: InChI=1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2

描述信息

Retronecine is a member of pyrrolizines.
Retronecine is a natural product found in Senecio nebrodensis, Lappula spinocarpos, and other organisms with data available.
Retronecine is a pyrrolizidine alkaloid found in a variety of plants in the genera Senecio and Crotalaria, and the family Boraginaceae. It is the most common central core for other pyrrolizidine alkaloids.
Origin: Plant; SubCategory_DNP: Alkaloids derived from ornithine, Pyrrolizidine alkaloids

同义名列表

25 个代谢物同义名

InChI=1/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s; 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1R-trans)-; 1H-Pyrrolizine-7-methanol, 2,3,5,7a-beta-tetrahydro-1-alpha-hydroxy-; (1r,7ar)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-ol; (1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol; (1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-ol; retronecine, monohydrochloride, (1S-trans)-isomer; retronecine, monohydrochloride, (1S-cis)-isomer; Retronecine, analytical standard; retronecine, (1S-cis)-isomer; RETRONECINE [HSDB]; RETRONECINE [MI]; UNII-2P5723M6II; ( )-Retronecine; (+)-Retronecine; Senecifolinene; heliotridine; Retronecine; Retronecin; 2P5723M6II; 1ST160717; 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1S-cis)-; Heliotridine; Retronecine; 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1S-cis)-



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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)

72 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 CASP3, CASP8, CASP9, CYP2D6, CYP3A4, HMGB1, HPGDS, PDLIM4, RARA
Peripheral membrane protein 3 CYP1B1, HMGB1, PDLIM4
Endoplasmic reticulum membrane 5 CYP1A2, CYP1B1, CYP2D6, CYP3A4, CYP3A5
Nucleus 8 CASP3, CASP8, CASP9, HMGB1, NR1I2, PARP1, PDLIM4, RARA
autophagosome 1 MAP1LC3A
cytosol 9 CASP3, CASP8, CASP9, GPT, HPGDS, MAP1LC3A, PARP1, PRF1, RARA
dendrite 1 RARA
nuclear body 2 NR1I2, PARP1
nucleoplasm 8 ATP2B1, CASP3, CASP8, HMGB1, HPGDS, NR1I2, PARP1, RARA
RNA polymerase II transcription regulator complex 1 RARA
Cell membrane 3 ATP2B1, HMGB1, PRF1
Lipid-anchor 1 MAP1LC3A
Cytoplasmic side 1 PDLIM4
lamellipodium 2 CASP8, PDLIM4
Early endosome membrane 1 PDLIM4
Multi-pass membrane protein 2 ATP2B1, PRF1
Synapse 2 ATP2B1, PDLIM4
cell surface 1 HMGB1
glutamatergic synapse 3 ATP2B1, CASP3, MAP1LC3A
Golgi apparatus 2 ATRN, TAS1R3
neuronal cell body 1 CASP3
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 1 PARP1
endosome 1 HMGB1
plasma membrane 6 ATP2B1, ATRN, HMGB1, PRF1, RARA, TAS1R3
synaptic vesicle membrane 1 ATP2B1
Membrane 8 ATP2B1, CYP1B1, CYP2D6, CYP3A4, CYP3A5, PARP1, PRF1, TAS1R3
basolateral plasma membrane 1 ATP2B1
extracellular exosome 3 ATP2B1, ATRN, GPT
endoplasmic reticulum 2 CYP2D6, HMGB1
extracellular space 2 ATRN, HMGB1
perinuclear region of cytoplasm 2 PDLIM4, RARA
adherens junction 1 PDLIM4
mitochondrion 5 CASP8, CASP9, CYP1B1, CYP2D6, PARP1
protein-containing complex 4 CASP8, CASP9, PARP1, RARA
intracellular membrane-bounded organelle 8 ATP2B1, CYP1A2, CYP1B1, CYP2D6, CYP3A4, CYP3A5, HPGDS, MAP1LC3A
Microsome membrane 5 CYP1A2, CYP1B1, CYP2D6, CYP3A4, CYP3A5
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 ATRN
Secreted 2 HMGB1, PRF1
extracellular region 2 HMGB1, PRF1
Single-pass membrane protein 1 CYP2D6
mitochondrial outer membrane 1 CASP8
[Isoform 2]: Secreted 1 ATRN
Extracellular side 1 HMGB1
transcription regulator complex 3 NR1I2, PARP1, RARA
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
actin cytoskeleton 1 RARA
dendritic spine 1 PDLIM4
Z disc 1 PDLIM4
nucleolus 2 PARP1, RARA
postsynaptic membrane 1 PDLIM4
Cell projection, lamellipodium 2 CASP8, PDLIM4
Cytoplasm, perinuclear region 1 PDLIM4
Cytoplasm, cytoskeleton 2 MAP1LC3A, PDLIM4
microtubule 1 MAP1LC3A
Cell projection, dendritic spine 1 PDLIM4
lateral plasma membrane 1 ATP2B1
Late endosome 1 MAP1LC3A
chromatin 3 NR1I2, PARP1, RARA
Cytoplasmic vesicle, autophagosome membrane 1 MAP1LC3A
autophagosome membrane 1 MAP1LC3A
cell projection 1 ATP2B1
Chromosome 2 HMGB1, PARP1
cytoskeleton 2 CASP8, PDLIM4
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Basolateral cell membrane 1 ATP2B1
organelle membrane 1 MAP1LC3A
site of double-strand break 1 PARP1
[Isoform 3]: Secreted 1 ATRN
nuclear envelope 1 PARP1
Recycling endosome membrane 1 PDLIM4
Endomembrane system 2 MAP1LC3A, PDLIM4
endosome lumen 1 PRF1
filamentous actin 1 PDLIM4
Presynaptic cell membrane 1 ATP2B1
cell body 1 CASP8
intermediate filament cytoskeleton 1 NR1I2
stress fiber 1 PDLIM4
ficolin-1-rich granule lumen 1 HMGB1
secretory granule lumen 1 HMGB1
transcription repressor complex 1 HMGB1
immunological synapse 2 ATP2B1, PRF1
apoptosome 1 CASP9
[Isoform 2]: Cytoplasm 1 PDLIM4
endoplasmic reticulum-Golgi intermediate compartment 1 HMGB1
Synapse, synaptosome 1 PDLIM4
protein-DNA complex 1 PARP1
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
[Isoform 1]: Cytoplasm, cytoskeleton 1 PDLIM4
[Isoform 1]: Cell membrane 1 ATRN
condensed chromosome 1 HMGB1
site of DNA damage 1 PARP1
Autolysosome 1 MAP1LC3A
alphav-beta3 integrin-HMGB1 complex 1 HMGB1
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
Cytolytic granule 1 PRF1
cytolytic granule lumen 1 PRF1
photoreceptor ribbon synapse 1 ATP2B1
early endosome lumen 1 PDLIM4
recycling endosome lumen 1 PDLIM4
caspase complex 1 CASP9
sweet taste receptor complex 1 TAS1R3


文献列表

  • Kyohei Takano, Hajime Ikeda, Kojiro Takanashi. Pyrrolizidine alkaloids are synthesized and accumulated in flower of Myosotis scorpioides. Journal of plant research. 2024 May; 137(3):455-462. doi: 10.1007/s10265-024-01525-4. [PMID: 38368590]
  • Lea A Barny, Julia A Tasca, Hugo A Sanchez, Chelsea R Smith, Suzanne Koptur, Tatyana Livshultz, Kevin P C Minbiole. Chemotaxonomic investigation of Apocynaceae for retronecine-type pyrrolizidine alkaloids using HPLC-MS/MS. Phytochemistry. 2021 May; 185(?):112662. doi: 10.1016/j.phytochem.2021.112662. [PMID: 33774572]
  • Fen Xiong, Kaiyuan Jiang, Yan Chen, Zhengcai Ju, Li Yang, Aizhen Xiong, Zhengtao Wang. Protein cross-linking in primary cultured mouse hepatocytes by dehydropyrrolizidine alkaloids: Structure-toxicity relationship. Toxicon : official journal of the International Society on Toxinology. 2020 Oct; 186(?):4-11. doi: 10.1016/j.toxicon.2020.07.015. [PMID: 32687888]
  • Verena Schöning, Felix Hammann, Mark Peinl, Jürgen Drewe. Editor's Highlight: Identification of Any Structure-Specific Hepatotoxic Potential of Different Pyrrolizidine Alkaloids Using Random Forests and Artificial Neural Networks. Toxicological sciences : an official journal of the Society of Toxicology. 2017 Dec; 160(2):361-370. doi: 10.1093/toxsci/kfx187. [PMID: 28973379]
  • Themístocles da Silva Negreiros Neto, Dale Gardner, Fernando Hallwass, Ana Jéssica Matias Leite, Camila Guimarães de Almeida, Laura Nunes Silva, Alan de Araújo Roque, Fernanda Gobbi de Bitencourt, Euzébio Guimarães Barbosa, Tiana Tasca, Alexandre José Macedo, Mauro Vieira de Almeida, Raquel Brandt Giordani. Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2016 Oct; 83(?):323-329. doi: 10.1016/j.biopha.2016.06.033. [PMID: 27399809]
  • Lin Zhu, Jian-Qing Ruan, Na Li, Peter P Fu, Yang Ye, Ge Lin. A novel ultra-performance liquid chromatography hyphenated with quadrupole time of flight mass spectrometry method for rapid estimation of total toxic retronecine-type of pyrrolizidine alkaloids in herbs without requiring corresponding standards. Food chemistry. 2016 Mar; 194(?):1320-8. doi: 10.1016/j.foodchem.2014.11.093. [PMID: 26471688]
  • Michael Boppré, Steven M Colegate. Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae). Phytochemical analysis : PCA. 2015 May; 26(3):215-25. doi: 10.1002/pca.2555. [PMID: 25645745]
  • Boris M Mandić, Marina D Vlajić, Snežana S Trifunović, Milena R Simić, Ljubodrag V Vujisić, Ivan M VuČković, Miroslav M Novaković, Snežana D Nikolić-Mandić, Vele V Tešević, Vlatka V Vajs, Slobodan M Milosavljević. Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge. Natural product research. 2015; 29(9):887-90. doi: 10.1080/14786419.2014.991929. [PMID: 25528897]
  • Carlos H Z Martins, Beatriz P Cunha, Vera N Solferini, José R Trigo. Feeding on Host Plants with Different Concentrations and Structures of Pyrrolizidine Alkaloids Impacts the Chemical-Defense Effectiveness of a Specialist Herbivore. PloS one. 2015; 10(10):e0141480. doi: 10.1371/journal.pone.0141480. [PMID: 26517873]
  • Eva Castells, Patrick P J Mulder, Míriam Pérez-Trujillo. Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): implications for toxicity. Phytochemistry. 2014 Dec; 108(?):137-46. doi: 10.1016/j.phytochem.2014.09.006. [PMID: 25269662]
  • Steven M Colegate, Dale R Gardner, T Zane Davis, Joseph M Betz, Kip E Panter. Dehydropyrrolizidine alkaloids in two Cryptantha species: including two new open chain diesters one of which is amphoteric. Phytochemical analysis : PCA. 2013 May; 24(3):201-12. doi: 10.1002/pca.2400. [PMID: 23070903]
  • Steven M Colegate, Dale R Gardner, Robert J Joy, Joseph M Betz, Kip E Panter. Dehydropyrrolizidine alkaloids, including monoesters with an unusual esterifying acid, from cultivated Crotalaria juncea (Sunn Hemp cv.'Tropic Sun'). Journal of agricultural and food chemistry. 2012 Apr; 60(14):3541-50. doi: 10.1021/jf205296s. [PMID: 22429238]
  • Yi-Cheng Yang, John Crowder, Nicholas J Wardle, Li Yang, Kenneth N White, Zheng-Tao Wang, S W Annie Bligh. ¹H NMR study of monocrotaline and its metabolites in human blood. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Nov; 49(11):2793-9. doi: 10.1016/j.fct.2011.07.063. [PMID: 21843583]
  • M Kempf, M Wittig, A Reinhard, K von der Ohe, T Blacquière, K-P Raezke, R Michel, P Schreier, T Beuerle. Pyrrolizidine alkaloids in honey: comparison of analytical methods. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2011 Mar; 28(3):332-47. doi: 10.1080/19440049.2010.521772. [PMID: 21082464]
  • Ai-Zhen Xiong, Li Yang, Fang Zhang, Xue-Jing Yang, Chang-Hong Wang, Zheng-Tao Wang. Determination of total retronecine esters-type hepatotoxic pyrrolizidine alkaloids in plant materials by pre-column derivatization high-performance liquid chromatography. Biomedical chromatography : BMC. 2009 Jun; 23(6):665-71. doi: 10.1002/bmc.1172. [PMID: 19277972]
  • Fang Zhang, Chang-hong Wang, Ai-zhen Xiong, Wan Wang, Li Yang, Christopher J Branford-White, Zheng-tao Wang, S W Annie Bligh. Quantitative analysis of total retronecine esters-type pyrrolizidine alkaloids in plant by high performance liquid chromatography. Analytica chimica acta. 2007 Dec; 605(1):94-101. doi: 10.1016/j.aca.2007.10.021. [PMID: 18022416]
  • Alex T Jordan, Tappey H Jones, William E Conner. Morphogenetic effects of alkaloidal metabolites on the development of the coremata in the salt marsh moth, Estigmene acrea (Dru.) (Lepidoptera: Arctiidae). Archives of insect biochemistry and physiology. 2007 Dec; 66(4):183-9. doi: 10.1002/arch.20211. [PMID: 18000873]
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