Neoglucobrassicin (BioDeep_00000003272)

   

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


{[(E)-[2-(1-methoxy-1H-indol-3-yl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid

化学式: C17H22N2O10S2 (478.0716)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 92.31%

分子结构信息

SMILES: c1ccc2c(c1)n(cc2C/C(=N/OS(=O)(=O)O)/S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)OC
InChI: InChI=1S/C17H22N2O10S2/c1-27-19-7-9(10-4-2-3-5-11(10)19)6-13(18-29-31(24,25)26)30-17-16(23)15(22)14(21)12(8-20)28-17/h2-5,7,12,14-17,20-23H,6,8H2,1H3,(H,24,25,26)/b18-13+

描述信息

Neoglucobrassicin, also known as MIMG, belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Outside of the human body, neoglucobrassicin has been detected, but not quantified in, several different foods, such as swedes, garden cress, Brussel sprouts, Chinese cabbages, and kohlrabis. This could make neoglucobrassicin a potential biomarker for the consumption of these foods. Neoglucobrassicin is widespread in Brassica species and found in the Cruciferae, Tovariaceae, Capparidaceae, and Resedaceae.
Widespread in Brassica subspecies and found in the Cruciferae, Tovariaceae, Capparidaceae and Resedaceae

同义名列表

11 个代谢物同义名

{[(E)-[2-(1-methoxy-1H-indol-3-yl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid; [(E)-[2-(1-methoxyindol-3-yl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxysulfonic acid; [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(1-methoxyindol-3-yl)-N-sulfooxyethanimidothioate; 1-Methoxy-3-indolylmethyl-glucosinolate; 1-Methoxy-3-indolylmethyl glucosinolate; 1-Methoxy-3-indolylmethylglucosinolate; 1-Methoxyglucobrassicin; Neoglucobrassicine; Neoglucobrassicin; MIMG; Neoglucobrassicin



数据库引用编号

21 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)

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 AHR, ALB, ARHGAP45, CDKN1A, CYP1A1, GPX2, GSTM1, HPGDS, NQO1, SULT1A1
Peripheral membrane protein 2 CYP1A1, PTPMT1
Endoplasmic reticulum membrane 1 CYP1A1
Nucleus 7 AHR, ALB, CDKN1A, GABPA, MYB, NQO1, PTPMT1
cytosol 11 AHR, ALB, ARHGAP45, CDKN1A, GLS, GPX2, GSTM1, HPGDS, MYB, NQO1, SULT1A1
dendrite 1 NQO1
nuclear body 1 CDKN1A
centrosome 1 ALB
nucleoplasm 5 AHR, CDKN1A, GABPA, HPGDS, MYB
RNA polymerase II transcription regulator complex 1 MYB
Cell membrane 1 GPR132
ruffle membrane 1 ARHGAP45
Multi-pass membrane protein 3 GPR132, SLC45A2, SLC7A7
Synapse 2 GLS, NQO1
Golgi apparatus 1 ALB
mitochondrial inner membrane 2 CYP1A1, PTPMT1
neuronal cell body 1 NQO1
Cytoplasm, cytosol 3 GLS, GPX2, NQO1
plasma membrane 3 ARHGAP45, GPR132, SLC7A7
Membrane 6 ARHGAP45, GPR132, MYB, NQO1, SLC45A2, SLC7A7
basolateral plasma membrane 1 SLC7A7
extracellular exosome 1 ALB
endoplasmic reticulum 1 ALB
extracellular space 2 ALB, COL2A1
perinuclear region of cytoplasm 1 CDKN1A
mitochondrion 3 CYP1A1, GLS, PTPMT1
protein-containing complex 3 AHR, ALB, CDKN1A
intracellular membrane-bounded organelle 2 CYP1A1, HPGDS
Microsome membrane 1 CYP1A1
Secreted 2 ALB, COL2A1
extracellular region 4 ALB, ARHGAP45, COL2A1, ESM1
mitochondrial matrix 1 GLS
anchoring junction 1 ALB
transcription regulator complex 1 AHR
Secreted, extracellular space, extracellular matrix 1 COL2A1
nucleolus 1 CDKN1A
Melanosome membrane 1 SLC45A2
Cell projection, ruffle membrane 1 ARHGAP45
Mitochondrion inner membrane 2 CYP1A1, PTPMT1
Matrix side 1 PTPMT1
basement membrane 1 COL2A1
collagen trimer 1 COL2A1
collagen-containing extracellular matrix 1 COL2A1
ciliary basal body 1 ALB
chromatin 2 AHR, GABPA
mitotic spindle 1 GPX2
centriole 1 ALB
[Isoform 1]: Mitochondrion 1 GLS
spindle pole 1 ALB
blood microparticle 1 ALB
Basolateral cell membrane 1 SLC7A7
intercellular bridge 2 GPX2, GSTM1
aryl hydrocarbon receptor complex 1 AHR
secretory granule lumen 1 ARHGAP45
endoplasmic reticulum lumen 2 ALB, COL2A1
nuclear matrix 1 MYB
platelet alpha granule lumen 1 ALB
azurophil granule lumen 1 ARHGAP45
[Isoform 3]: Mitochondrion 1 GLS
cyclin-dependent protein kinase holoenzyme complex 1 CDKN1A
[Glutaminase kidney isoform, mitochondrial 68 kDa chain]: Mitochondrion matrix 1 GLS
[Glutaminase kidney isoform, mitochondrial 65 kDa chain]: Mitochondrion matrix 1 GLS
collagen type II trimer 1 COL2A1
collagen type XI trimer 1 COL2A1
PCNA-p21 complex 1 CDKN1A
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
ciliary transition fiber 1 ALB


文献列表

  • Hansruedi Glatt, Wolfram Engst, Simone Florian, Monika Schreiner, Chimgee Baasanjav-Gerber. Feeding Brassica vegetables to rats leads to the formation of characteristic DNA adducts (from 1-methoxy-3-indolylmethyl glucosinolate) in many tissues. Archives of toxicology. 2022 03; 96(3):933-944. doi: 10.1007/s00204-021-03216-8. [PMID: 34997255]
  • Melanie Wiesner-Reinhold, Gitte Barknowitz, Simone Florian, Inga Mewis, Fabian Schumacher, Monika Schreiner, Hansruedi Glatt. 1-Methoxy-3-indolylmethyl DNA adducts in six tissues, and blood protein adducts, in mice under pak choi diet: time course and persistence. Archives of toxicology. 2019 06; 93(6):1515-1527. doi: 10.1007/s00204-019-02452-3. [PMID: 30993378]
  • Doris Lippmann, Carsten Lehmann, Simone Florian, Gitte Barknowitz, Michael Haack, Inga Mewis, Melanie Wiesner, Monika Schreiner, Hansruedi Glatt, Regina Brigelius-Flohé, Anna P Kipp. Glucosinolates from pak choi and broccoli induce enzymes and inhibit inflammation and colon cancer differently. Food & function. 2014 Jun; 5(6):1073-81. doi: 10.1039/c3fo60676g. [PMID: 24714741]
  • Melanie Wiesner, Monika Schreiner, Rita Zrenner. Functional identification of genes responsible for the biosynthesis of 1-methoxy-indol-3-ylmethyl-glucosinolate in Brassica rapa ssp. chinensis. BMC plant biology. 2014 May; 14(?):124. doi: 10.1186/1471-2229-14-124. [PMID: 24886080]
  • Melanie Wiesner, Monika Schreiner, Hansruedi Glatt. High mutagenic activity of juice from pak choi (Brassica rapa ssp. chinensis) sprouts due to its content of 1-methoxy-3-indolylmethyl glucosinolate, and its enhancement by elicitation with methyl jasmonate. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 May; 67(?):10-6. doi: 10.1016/j.fct.2014.02.008. [PMID: 24530313]
  • Fabian Schumacher, Simone Florian, Anke Schnapper, Bernhard H Monien, Inga Mewis, Monika Schreiner, Albrecht Seidel, Wolfram Engst, Hansruedi Glatt. A secondary metabolite of Brassicales, 1-methoxy-3-indolylmethyl glucosinolate, as well as its degradation product, 1-methoxy-3-indolylmethyl alcohol, forms DNA adducts in the mouse, but in varying tissues and cells. Archives of toxicology. 2014 Mar; 88(3):823-36. doi: 10.1007/s00204-013-1149-7. [PMID: 24154822]
  • Gitte Barknowitz, Wolfram Engst, Stephan Schmidt, Mareike Bernau, Bernhard H Monien, Markus Kramer, Simone Florian, Hansruedi Glatt. Identification and quantification of protein adducts formed by metabolites of 1-methoxy-3-indolylmethyl glucosinolate in vitro and in mouse models. Chemical research in toxicology. 2014 Feb; 27(2):188-99. doi: 10.1021/tx400277w. [PMID: 24422435]
  • Fabian Schumacher, Wolfram Engst, Bernhard H Monien, Simone Florian, Anke Schnapper, Lisa Steinhauser, Klaus Albert, Heinz Frank, Albrecht Seidel, Hansruedi Glatt. Detection of DNA adducts originating from 1-methoxy-3-indolylmethyl glucosinolate using isotope-dilution UPLC-ESI-MS/MS. Analytical chemistry. 2012 Jul; 84(14):6256-62. doi: 10.1021/ac301436q. [PMID: 22816785]
  • Klaus Peter Latté, Klaus-Erich Appel, Alfonso Lampen. Health benefits and possible risks of broccoli - an overview. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Dec; 49(12):3287-309. doi: 10.1016/j.fct.2011.08.019. [PMID: 21906651]
  • Jeffrey A Harvey, Nicole M van Dam, Ciska E Raaijmakers, James M Bullock, Rieta Gols. Tri-trophic effects of inter- and intra-population variation in defence chemistry of wild cabbage (Brassica oleracea). Oecologia. 2011 Jun; 166(2):421-31. doi: 10.1007/s00442-010-1861-4. [PMID: 21140168]
  • Jeroen J Jansen, Nicole M van Dam, Huub C J Hoefsloot, Age K Smilde. Crossfit analysis: a novel method to characterize the dynamics of induced plant responses. BMC bioinformatics. 2009 Dec; 10(?):425. doi: 10.1186/1471-2105-10-425. [PMID: 20015363]
  • Rieta Gols, R Wagenaar, Tibor Bukovinszky, Nicole M van Dam, Marcel Dicke, James M Bullock, Jeffrey A Harvey. Genetic variation in defense chemistry in wild cabbages affects herbivores and their endoparasitoids. Ecology. 2008 Jun; 89(6):1616-26. doi: 10.1890/07-0873.1. [PMID: 18589526]
  • Yun-Xiang Zang, Myung-Ho Lim, Beom-Seok Park, Seung-Beom Hong, Doo Hwan Kim. Metabolic engineering of indole glucosinolates in Chinese cabbage plants by expression of Arabidopsis CYP79B2, CYP79B3, and CYP83B1. Molecules and cells. 2008 Apr; 25(2):231-41. doi: . [PMID: 18414013]
  • Jules Beekwilder, Wessel van Leeuwen, Nicole M van Dam, Monica Bertossi, Valentina Grandi, Luca Mizzi, Mikhail Soloviev, Laszlo Szabados, Jos W Molthoff, Bert Schipper, Hans Verbocht, Ric C H de Vos, Piero Morandini, Mark G M Aarts, Arnaud Bovy. The impact of the absence of aliphatic glucosinolates on insect herbivory in Arabidopsis. PloS one. 2008 Apr; 3(4):e2068. doi: 10.1371/journal.pone.0002068. [PMID: 18446225]
  • Rieta Gols, Tibor Bukovinszky, Nicole M van Dam, Marcel Dicke, James M Bullock, Jeffrey A Harvey. Performance of generalist and specialist herbivores and their endoparasitoids differs on cultivated and wild Brassica populations. Journal of chemical ecology. 2008 Feb; 34(2):132-43. doi: 10.1007/s10886-008-9429-z. [PMID: 18231835]
  • Hanneke van Leur, Louise E M Vet, Wim H van der Putten, Nicole M van Dam. Barbarea vulgaris glucosinolate phenotypes differentially affect performance and preference of two different species of lepidopteran herbivores. Journal of chemical ecology. 2008 Feb; 34(2):121-31. doi: 10.1007/s10886-007-9424-9. [PMID: 18213497]
  • L Filippo D'Antuono, Simona Elementi, Roberta Neri. Glucosinolates in Diplotaxis and Eruca leaves: diversity, taxonomic relations and applied aspects. Phytochemistry. 2008 Jan; 69(1):187-99. doi: 10.1016/j.phytochem.2007.06.019. [PMID: 17669448]
  • Jeffrey A Harvey, Rieta Gols, Roel Wagenaar, T Martijn Bezemer. Development of an insect herbivore and its pupal parasitoid reflect differences in direct plant defense. Journal of chemical ecology. 2007 Aug; 33(8):1556-69. doi: 10.1007/s10886-007-9323-0. [PMID: 17587139]
  • Roxina Soler, T Martijn Bezemer, Anne Marie Cortesero, Wim H Van der Putten, Louise E M Vet, Jeffrey A Harvey. Impact of foliar herbivory on the development of a root-feeding insect and its parasitoid. Oecologia. 2007 May; 152(2):257-64. doi: 10.1007/s00442-006-0649-z. [PMID: 17334787]
  • Markus Piotrowski, Andreas Schemenewitz, Anna Lopukhina, Axel Müller, Tim Janowitz, Elmar W Weiler, Claudia Oecking. Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure. The Journal of biological chemistry. 2004 Dec; 279(49):50717-25. doi: 10.1074/jbc.m407681200. [PMID: 15358770]
  • Xian Li, Mosbah M Kushad. Correlation of glucosinolate content to myrosinase activity in horseradish (Armoracia rusticana). Journal of agricultural and food chemistry. 2004 Nov; 52(23):6950-5. doi: 10.1021/jf0401827. [PMID: 15537302]
  • O Vang, H Frandsen, K T Hansen, J N Sørensen, H Sørensen, O Andersen. Biochemical effects of dietary intakes of different broccoli samples. I. Differential modulation of cytochrome P-450 activities in rat liver, kidney, and colon. Metabolism: clinical and experimental. 2001 Oct; 50(10):1123-9. doi: 10.1053/meta.2001.26743. [PMID: 11586481]
  • O Vang, J Mortensen, O Andersen. Biochemical effects of dietary intake of different broccoli samples. II. Multivariate analysis of contributions of specific glucosinolates in modulating cytochrome P-450 and antioxidant defense enzyme activities. Metabolism: clinical and experimental. 2001 Oct; 50(10):1130-5. doi: 10.1053/meta.2001.26744. [PMID: 11586482]
  • E Andreasson, S Wretblad, G Granér, X Wu, J Zhang, C Dixelius, L Rask, J Meijer. The myrosinase-glucosinolate system in the interaction between Leptosphaeria maculans and Brassica napus. Molecular plant pathology. 2001 Sep; 2(5):281-6. doi: 10.1046/j.1464-6722.2001.00076.x. [PMID: 20573016]