Tropine (BioDeep_00000184599)

Main id: BioDeep_00000000990

 

human metabolite blood metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


8-Methyl-8-azabicyclo[3.2.1]octan-3-ol

化学式: C8H15NO (141.1154)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN1C2CCC1CC(C2)O
InChI: InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3

描述信息

Pseudotropine, also known as tropine hydrochloride, (endo)-isomer or tropine, (exo)-isomer, is a member of the class of compounds known as tropane alkaloids. Tropane alkaloids are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Pseudotropine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Pseudotropine can be found in a number of food items such as winter savory, japanese chestnut, blackcurrant, and black walnut, which makes pseudotropine a potential biomarker for the consumption of these food products. Pseudotropine (3β-tropanol, ψ-tropine, 3-pseudotropanol or PTO) is a derivative of tropane and an isomer of tropine .
Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].
Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].

同义名列表

11 个代谢物同义名

8-Methyl-8-azabicyclo[3.2.1]octan-3-ol; tropine hydrochloride, (endo)-isomer; tropine hydrobromide, (endo)-isomer; tropine hydrochloride, (exo)-isomer; tropine, (exo)-isomer; Pseudotropine; Tropine; tropin; Pseudotropine; Tropine; Tropine



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)

163 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 10 ABCB1, AR, ATN1, AZIN2, DDB1, DICER1, HTR4, MAB21L2, ODC1, SOX10
Peripheral membrane protein 1 SOX10
Endosome membrane 1 HTR4
Endoplasmic reticulum membrane 1 UGT1A1
Nucleus 8 AR, ATN1, AZIN2, DDB1, DICER1, MAB21L1, MAB21L2, SOX10
cytosol 5 AR, AZIN2, DICER1, ODC1, TBATA
dendrite 3 AZIN2, DRD2, HTR4
trans-Golgi network 1 AZIN2
nucleoplasm 4 AR, ATN1, DDB1, SOX10
Cell membrane 6 ABCB1, ADRB3, DRD2, GLRA2, HTR3A, HTR4
Cytoplasmic side 1 SOX10
Cleavage furrow 1 HTR3A
Multi-pass membrane protein 6 ABCB1, ADRB3, DRD2, GLRA2, HTR3A, HTR4
Golgi apparatus membrane 1 DRD2
Synapse 4 DRD2, GLRA2, HTR3A, HTR4
cell junction 1 ATN1
cell surface 1 ABCB1
glutamatergic synapse 2 DRD2, HTR4
Golgi membrane 1 DRD2
postsynapse 2 HTR3A, HTR4
presynaptic membrane 1 DRD2
Cytoplasm, cytosol 1 TBATA
acrosomal vesicle 1 DRD2
endosome 1 HTR4
plasma membrane 10 ABCB1, ADRB3, AR, DRD2, GLRA2, HTR3A, HTR4, KNG1, SERPINC1, UGT1A1
synaptic vesicle membrane 1 DRD2
Membrane 7 ABCB1, AR, AZIN2, GLRA2, HTR3A, HTR4, UGT1A1
apical plasma membrane 1 ABCB1
axon 2 AZIN2, DRD2
extracellular exosome 6 ABCB1, COL1A2, DDB1, DICER1, KNG1, SERPINC1
endoplasmic reticulum 1 UGT1A1
extracellular space 4 COL1A2, DDB1, KNG1, SERPINC1
perinuclear region of cytoplasm 4 ATN1, AZIN2, DICER1, UGT1A1
mitochondrion 1 AZIN2
protein-containing complex 2 AR, DDB1
intracellular membrane-bounded organelle 1 GLRA2
Secreted 1 COL1A2
extracellular region 3 COL1A2, KNG1, SERPINC1
Mitochondrion outer membrane 1 SOX10
Single-pass membrane protein 1 UGT1A1
mitochondrial outer membrane 1 SOX10
anchoring junction 1 ATN1
ciliary membrane 1 DRD2
Secreted, extracellular space, extracellular matrix 1 COL1A2
dendritic spine 1 DRD2
perikaryon 2 AZIN2, DRD2
cytoplasmic vesicle 1 AZIN2
nucleolus 1 DDB1
postsynaptic membrane 2 DRD2, HTR3A
Apical cell membrane 1 ABCB1
Cytoplasm, perinuclear region 2 DICER1, UGT1A1
GABA-ergic synapse 2 DRD2, GLRA2
cis-Golgi network 1 AZIN2
collagen trimer 1 COL1A2
collagen-containing extracellular matrix 3 COL1A2, KNG1, SERPINC1
lateral plasma membrane 1 DRD2
nuclear speck 1 AR
Postsynaptic cell membrane 2 GLRA2, HTR3A
receptor complex 1 ADRB3
neuron projection 2 GLRA2, HTR3A
ciliary basal body 1 TBATA
cilium 1 DRD2
chromatin 2 AR, SOX10
cell projection 1 GLRA2
Secreted, extracellular space 2 KNG1, SERPINC1
chromosome, telomeric region 1 DDB1
blood microparticle 2 KNG1, SERPINC1
non-motile cilium 1 DRD2
serotonin-activated cation-selective channel complex 1 HTR3A
transmembrane transporter complex 2 GLRA2, HTR3A
site of double-strand break 1 DDB1
sperm flagellum 1 DRD2
chloride channel complex 1 GLRA2
endoplasmic reticulum lumen 3 COL1A2, KNG1, SERPINC1
nuclear matrix 1 ATN1
platelet alpha granule lumen 1 KNG1
axon terminus 1 DRD2
endocytic vesicle 1 DRD2
transport vesicle 1 AZIN2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 AZIN2
endoplasmic reticulum-Golgi intermediate compartment 1 AZIN2
external side of apical plasma membrane 1 ABCB1
postsynaptic specialization membrane 1 GLRA2
dopaminergic synapse 1 DRD2
Golgi apparatus, cis-Golgi network 1 AZIN2
RISC complex 1 DICER1
RISC-loading complex 1 DICER1
collagen type I trimer 1 COL1A2
glycinergic synapse 1 GLRA2
endoplasmic reticulum chaperone complex 1 UGT1A1
G protein-coupled receptor complex 1 DRD2
cytochrome complex 1 UGT1A1
Cul4A-RING E3 ubiquitin ligase complex 1 DDB1
Cul4-RING E3 ubiquitin ligase complex 1 DDB1
Cul4B-RING E3 ubiquitin ligase complex 1 DDB1
granular vesicle 1 AZIN2


文献列表

  • Monique de Nijs, Colin Crews, Folke Dorgelo, Susan MacDonald, Patrick P J Mulder. Emerging Issues on Tropane Alkaloid Contamination of Food in Europe. Toxins. 2023 Jan; 15(2):. doi: 10.3390/toxins15020098. [PMID: 36828413]
  • Radin Sadre, Thilani M Anthony, Josh M Grabar, Matthew A Bedewitz, A Daniel Jones, Cornelius S Barry. Metabolomics-guided discovery of cytochrome P450s involved in pseudotropine-dependent biosynthesis of modified tropane alkaloids. Nature communications. 2022 07; 13(1):3832. doi: 10.1038/s41467-022-31653-1. [PMID: 35780230]
  • Prashanth Srinivasan, Christina D Smolke. Engineering a microbial biosynthesis platform for de novo production of tropane alkaloids. Nature communications. 2019 08; 10(1):3634. doi: 10.1038/s41467-019-11588-w. [PMID: 31406117]
  • Jesús Marín-Sáez, Roberto Romero-González, Antonia Garrido Frenich. Degradation of tropane alkaloids in baked bread samples contaminated with Solanaceae seeds. Food research international (Ottawa, Ont.). 2019 08; 122(?):585-592. doi: 10.1016/j.foodres.2019.01.027. [PMID: 31229117]
  • Jesús Marín-Sáez, Roberto Romero-González, Antonia Garrido Frenich. Effect of tea making and boiling processes on the degradation of tropane alkaloids in tea and pasta samples contaminated with Solanaceae seeds and coca leaf. Food chemistry. 2019 Jul; 287(?):265-272. doi: 10.1016/j.foodchem.2019.02.091. [PMID: 30857698]
  • Yu Ping, Xiaodong Li, Wenjing You, Guoqiang Li, Mengquan Yang, Wenping Wei, Zhihua Zhou, Youli Xiao. De Novo Production of the Plant-Derived Tropine and Pseudotropine in Yeast. ACS synthetic biology. 2019 06; 8(6):1257-1262. doi: 10.1021/acssynbio.9b00152. [PMID: 31181154]
  • Katarzyna M Romek, Gérald S Remaud, Virginie Silvestre, Piotr Paneth, Richard J Robins. Non-statistical 13C Fractionation Distinguishes Co-incident and Divergent Steps in the Biosynthesis of the Alkaloids Nicotine and Tropine. The Journal of biological chemistry. 2016 08; 291(32):16620-9. doi: 10.1074/jbc.m116.734087. [PMID: 27288405]
  • Amit K Kushwaha, Neelam S Sangwan, Sandhya Tripathi, Rajender S Sangwan. Molecular cloning and catalytic characterization of a recombinant tropine biosynthetic tropinone reductase from Withania coagulans leaf. Gene. 2013 Mar; 516(2):238-47. doi: 10.1016/j.gene.2012.11.091. [PMID: 23266822]
  • Amit Kumar Kushwaha, Neelam Singh Sangwan, Prabodh Kumar Trivedi, Arvind Singh Negi, Laxminarain Misra, Rajender Singh Sangwan. Tropine forming tropinone reductase gene from Withania somnifera (Ashwagandha): biochemical characteristics of the recombinant enzyme and novel physiological overtones of tissue-wide gene expression patterns. PloS one. 2013; 8(9):e74777. doi: 10.1371/journal.pone.0074777. [PMID: 24086372]
  • Andrea Brock, Wolfgang Brandt, Birgit Dräger. The functional divergence of short-chain dehydrogenases involved in tropinone reduction. The Plant journal : for cell and molecular biology. 2008 May; 54(3):388-401. doi: 10.1111/j.1365-313x.2008.03422.x. [PMID: 18221363]
  • Heike Kaiser, Ute Richter, Ronald Keiner, Anja Brabant, Bettina Hause, Birgit Dräger. Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts. Planta. 2006 Dec; 225(1):127-37. doi: 10.1007/s00425-006-0335-8. [PMID: 16845528]
  • Birgit Dräger. Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. Phytochemistry. 2006 Feb; 67(4):327-37. doi: 10.1016/j.phytochem.2005.12.001. [PMID: 16426652]
  • Rawia Zayed, Michael Wink. Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae). Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Nov; 59(11-12):863-7. doi: 10.1515/znc-2004-11-1216. [PMID: 15666547]
  • Grit Rothe, Akira Hachiya, Yasuyuki Yamada, Takashi Hashimoto, Birgit Dräger. Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase. Journal of experimental botany. 2003 Sep; 54(390):2065-70. doi: 10.1093/jxb/erg227. [PMID: 12885861]
  • E W Moore, J M Hunter. The new neuromuscular blocking agents: do they offer any advantages?. British journal of anaesthesia. 2001 Dec; 87(6):912-25. doi: 10.1093/bja/87.6.912. [PMID: 11878696]
  • P C Schultheiss, A P Knight, J L Traub-Dargatz, F G Todd, F R Stermitz. Toxicity of field bindweed (Convolvulus arvensis) to mice. Veterinary and human toxicology. 1995 Oct; 37(5):452-4. doi: . [PMID: 8592835]
  • H He, G McKay, K K Midha. Phase I and II metabolites of benztropine in rat urine and bile. Xenobiotica; the fate of foreign compounds in biological systems. 1995 Aug; 25(8):857-72. doi: 10.3109/00498259509061899. [PMID: 8779226]
  • M J Van der Meer, H K Hundt, F O Müller. The metabolism of atropine in man. The Journal of pharmacy and pharmacology. 1986 Oct; 38(10):781-4. doi: 10.1111/j.2042-7158.1986.tb04494.x. [PMID: 2879005]
  • P H Hinderling, U Gundert-Remy, O Schmidlin. Integrated pharmacokinetics and pharmacodynamics of atropine in healthy humans. I: Pharmacokinetics. Journal of pharmaceutical sciences. 1985 Jul; 74(7):703-10. doi: 10.1002/jps.2600740702. [PMID: 4032240]
  • M Eckert, P H Hinderling. Atropine: a sensitive gas chromatography-mass spectrometry assay and prepharmacokinetic studies. Agents and actions. 1981 Nov; 11(5):520-31. doi: 10.1007/bf02004716. [PMID: 7337075]
  • O O Barriga. Depression of cell-mediated immunity following inoculation of Trichinella spiralis extract in the mouse. Immunology. 1978 Jan; 34(1):167-73. doi: NULL. [PMID: 23994]