Linamarin (BioDeep_00000000674)

 

Secondary id: BioDeep_00000407855

human metabolite PANOMIX_OTCML-2023 Antitumor activity natural product


代谢物信息卡片


2-Methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propanenitrile

化学式: C10H17NO6 (247.1056)
中文名称: 亞麻苷, 亚麻苦苷
谱图信息: 最多检出来源 Viridiplantae(plant) 9.48%

分子结构信息

SMILES: CC(C)(C#N)OC1C(C(C(C(O1)CO)O)O)O
InChI: InChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1

描述信息

Linamarin is a beta-D-glucoside. It is functionally related to a 2-hydroxy-2-methylpropanenitrile.
Linamarin is a natural product found in Osteospermum ecklonis, Lotus arenarius, and other organisms with data available.
Linamarin is found in coffee and coffee products. Linamarin occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isloated in 1830.
Occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isol in 1830. Linamarin is found in many foods, some of which are gooseberry, chinese broccoli, cascade huckleberry, and leek.
Linamarin is found in coffee and coffee products. Linamarin occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isloated in 1830.
Linamarin, a natural compound, possesses anticancer activity[1].
Linamarin, a natural compound, possesses anticancer activity[1].

同义名列表

37 个代谢物同义名

2-Methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propanenitrile; 2-methyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)propanenitrile; 2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile; 2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile; alpha-Hydroxyisobutyronitrile beta-D-glucopyranoside, >=98.0\\% (HPLC); Propanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-; 2-(.BETA.-D-GLUCOPYRANOSYLOXY)-2-METHYLPROPANENITRILE; 2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9CI; 2-(beta-D-Glucopyranosyloxy)-2-methyl-Propanenitrile; alpha-Hydroxyisobutyronitrile beta-D-glucopyranoside; 2-(beta-D-Glucopyranosyloxy)-2-methylpropanenitrile; 2-beta-d-glucopyranosyloxy-2-methylpropanenitrile; alpha-Hydroxyisobutyronitrile-beta-D-glucose; 5-17-07-00397 (Beilstein Handbook Reference); 2-(beta-D-Glucopyranosyloxy)isobutyronitrile; 1-cyano-1-methylethyl beta-D-glucoside; 1-Cyano-1-methylethyl b-D-glucoside; 1-Cyano-1-methylethyl β-D-glucoside; Linamarin min. 99\\%; Spectrum5_000575; Spectrum3_001622; Spectrum4_001668; LINAMARIN [HSDB]; Spectrum2_001972; UNII-H3V9RP3WLO; LINAMARIN [MI]; DivK1c_007032; phaseolunatin; KBio3_002503; KBio2_007628; KBio1_001976; KBio2_002492; KBio2_005060; Manihotoxin; H3V9RP3WLO; Linamarin; Linamarin



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(4)

PlantCyc(4)

代谢反应

48 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(5)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(43)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

173 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 ALB, BNIP3, CA1, CASP3, DNM1, ITPR3, PRDX6, TH, WT1
Peripheral membrane protein 2 CYP1B1, GBA1
Endoplasmic reticulum membrane 3 BNIP3, CYP1B1, ITPR3
Mitochondrion membrane 1 BNIP3
Nucleus 7 ALB, BNIP3, CASP3, PARP1, PRDX6, TH, WT1
cytosol 10 ACACA, ALB, CA1, CASP3, GPT, HCCS, PARP1, PRDX6, TH, WT1
dendrite 2 BNIP3, TH
mitochondrial membrane 1 BNIP3
nuclear body 1 PARP1
trans-Golgi network 1 GBA1
centrosome 1 ALB
nucleoplasm 5 BNIP3, CASP3, ITPR3, PARP1, WT1
Cell membrane 3 DNM1, ITGAM, P2RY4
Lipid-anchor 1 HCCS
Cell projection, axon 1 TH
Multi-pass membrane protein 4 ITPR3, P2RY4, SLC5A1, SLC7A7
Synapse 1 DNM1
cell surface 1 ITGAM
glutamatergic synapse 3 CASP3, DNM1, P2RY4
Golgi apparatus 2 ALB, GBA1
lysosomal membrane 1 GBA1
mitochondrial inner membrane 1 HCCS
neuronal cell body 2 CASP3, ITPR3
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Cytoplasm, cytosol 2 ACACA, PARP1
Lysosome 2 GBA1, PRDX6
Presynapse 1 DNM1
plasma membrane 6 DNM1, ITGAM, ITPR3, P2RY4, SLC5A1, SLC7A7
terminal bouton 1 TH
Membrane 8 BNIP3, CYP1B1, HCCS, ITGAM, ITPR3, PARP1, PRDX6, SLC7A7
apical plasma membrane 2 P2RY4, SLC5A1
axon 1 TH
basolateral plasma membrane 2 P2RY4, SLC7A7
brush border 1 ITPR3
extracellular exosome 8 ALB, CA1, DNM1, GBA1, GPT, ITGAM, PRDX6, SLC5A1
Lysosome membrane 1 GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 4 ALB, BNIP3, GBA1, ITPR3
extracellular space 4 ALB, ITGAM, PRDX6, TST
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 3 PRDX6, SLC5A1, TH
mitochondrion 8 ACACA, BNIP3, CYP1B1, HCCS, PARP1, PRDX6, TH, TST
protein-containing complex 2 ALB, PARP1
intracellular membrane-bounded organelle 1 CYP1B1
Microsome membrane 1 CYP1B1
postsynaptic density 2 BNIP3, CASP3
Single-pass type I membrane protein 1 ITGAM
Secreted 1 ALB
extracellular region 2 ALB, PRDX6
cytoplasmic side of plasma membrane 1 TH
Single-pass membrane protein 1 BNIP3
mitochondrial outer membrane 1 BNIP3
Mitochondrion matrix 1 TST
mitochondrial matrix 1 TST
anchoring junction 1 ALB
transcription regulator complex 1 PARP1
photoreceptor inner segment 1 DNM1
external side of plasma membrane 1 ITGAM
actin cytoskeleton 1 ACACA
perikaryon 1 TH
cytoplasmic vesicle 2 DNM1, TH
nucleolus 3 ITPR3, PARP1, WT1
Melanosome membrane 1 TH
Early endosome 1 SLC5A1
Membrane, clathrin-coated pit 1 DNM1
apical part of cell 1 ITPR3
clathrin-coated pit 1 DNM1
presynaptic active zone membrane 1 P2RY4
Apical cell membrane 1 SLC5A1
Cytoplasm, perinuclear region 1 TH
Mitochondrion inner membrane 1 HCCS
Membrane raft 1 ITGAM
microtubule 1 DNM1
intracellular vesicle 1 SLC5A1
sarcoplasmic reticulum 1 ITPR3
nuclear speck 1 WT1
nuclear outer membrane 1 ITPR3
receptor complex 1 ITPR3
neuron projection 1 TH
ciliary basal body 1 ALB
chromatin 1 PARP1
cell projection 1 DNM1
Chromosome 1 PARP1
centriole 1 ALB
brush border membrane 1 SLC5A1
Nucleus, nucleolus 1 PARP1
spindle pole 1 ALB
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
blood microparticle 1 ALB
Basolateral cell membrane 1 SLC7A7
site of double-strand break 1 PARP1
fibrillar center 1 ACACA
nuclear envelope 2 BNIP3, PARP1
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
Nucleus speckle 1 WT1
plasma membrane raft 1 ITGAM
secretory granule membrane 1 ITPR3
endoplasmic reticulum lumen 1 ALB
platelet alpha granule lumen 1 ALB
endocytic vesicle 1 DNM1
azurophil granule lumen 1 PRDX6
mitochondrial envelope 1 BNIP3
platelet dense tubular network membrane 1 ITPR3
protein-DNA complex 1 PARP1
death-inducing signaling complex 1 CASP3
membrane coat 1 DNM1
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
site of DNA damage 1 PARP1
integrin complex 1 ITGAM
transport vesicle membrane 1 ITPR3
integrin alphaM-beta2 complex 1 ITGAM
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule 1 DNM1
chromaffin granule 1 DNM1
presynaptic endocytic zone membrane 1 DNM1
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
photoreceptor ribbon synapse 1 DNM1
intracellular organelle 1 SLC5A1
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
[Isoform 1]: Nucleus speckle 1 WT1
[Isoform 4]: Nucleus, nucleoplasm 1 WT1
ciliary transition fiber 1 ALB


文献列表

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  • Youn Young Shim, Clara M Olivia, Jun Liu, Rineke Boonen, Jianheng Shen, Martin J T Reaney. Secoisolariciresinol Diglucoside and Cyanogenic Glycosides in Gluten-free Bread Fortified with Flaxseed Meal. Journal of agricultural and food chemistry. 2016 Dec; 64(50):9551-9558. doi: 10.1021/acs.jafc.6b03962. [PMID: 27998066]
  • Daniela Lai, Martina Pičmanová, Maher Abou Hachem, Mohammed Saddik Motawia, Carl Erik Olsen, Birger Lindberg Møller, Fred Rook, Adam M Takos. Lotus japonicus flowers are defended by a cyanogenic β-glucosidase with highly restricted expression to essential reproductive organs. Plant molecular biology. 2015 Sep; 89(1-2):21-34. doi: 10.1007/s11103-015-0348-4. [PMID: 26249044]
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  • M Sulyok, F Beed, S Boni, A Abass, A Mukunzi, R Krska. Quantitation of multiple mycotoxins and cyanogenic glucosides in cassava samples from Tanzania and Rwanda by an LC-MS/MS-based multi-toxin method. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(4):488-502. doi: 10.1080/19440049.2014.975752. [PMID: 25350522]
  • Joel Fürstenberg-Hägg, Mika Zagrobelny, Kirsten Jørgensen, Heiko Vogel, Birger Lindberg Møller, Søren Bak. Chemical defense balanced by sequestration and de novo biosynthesis in a lepidopteran specialist. PloS one. 2014; 9(10):e108745. doi: 10.1371/journal.pone.0108745. [PMID: 25299618]
  • Eduardo Rivadeneyra-Domínguez, Alma Vázquez-Luna, Juan Francisco Rodríguez-Landa, Rafael Díaz-Sobac. Neurotoxic effect of linamarin in rats associated with cassava (Manihot esculenta Crantz) consumption. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Sep; 59(?):230-5. doi: 10.1016/j.fct.2013.06.004. [PMID: 23778051]
  • Jumat Salimon, Bashar Mudhaffar Abdullah, Nadia Salih. Rubber (Hevea brasiliensis) seed oil toxicity effect and Linamarin compound analysis. Lipids in health and disease. 2012 Jun; 11(?):74. doi: 10.1186/1476-511x-11-74. [PMID: 22694753]
  • Shigeki Saito, Mohammed Saddik Motawia, Carl Erik Olsen, Birger Lindberg Møller, Søren Bak. Biosynthesis of rhodiocyanosides in Lotus japonicus: rhodiocyanoside A is synthesized from (Z)-2-methylbutanaloxime via 2-methyl-2-butenenitrile. Phytochemistry. 2012 May; 77(?):260-7. doi: 10.1016/j.phytochem.2012.01.020. [PMID: 22385904]
  • Willie Girald, Alejandro Collin, Marta Izquierdo. Toxicity and delivery methods for the linamarase/linamarin/glucose oxidase system, when used against human glioma tumors implanted in the brain of nude rats. Cancer letters. 2011 Dec; 313(1):99-107. doi: 10.1016/j.canlet.2011.08.029. [PMID: 21955616]
  • Rubini Kannangara, Mohammed S Motawia, Natascha K K Hansen, Suzanne M Paquette, Carl E Olsen, Birger L Møller, Kirsten Jørgensen. Characterization and expression profile of two UDP-glucosyltransferases, UGT85K4 and UGT85K5, catalyzing the last step in cyanogenic glucoside biosynthesis in cassava. The Plant journal : for cell and molecular biology. 2011 Oct; 68(2):287-301. doi: 10.1111/j.1365-313x.2011.04695.x. [PMID: 21736650]
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  • Joabe Gomes de Melo, Ariane Gaspar Santos, Elba Lúcia Cavalcanti de Amorim, Silene Carneiro do Nascimento, Ulysses Paulino de Albuquerque. Medicinal plants used as antitumor agents in Brazil: an ethnobotanical approach. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):365359. doi: 10.1155/2011/365359. [PMID: 21528006]
  • Narayanan N Narayanan, Uzoma Ihemere, Claire Ellery, Richard T Sayre. Overexpression of hydroxynitrile lyase in cassava roots elevates protein and free amino acids while reducing residual cyanogen levels. PloS one. 2011; 6(7):e21996. doi: 10.1371/journal.pone.0021996. [PMID: 21799761]
  • Niels Bjerg Jensen, Mika Zagrobelny, Karin Hjernø, Carl Erik Olsen, Jens Houghton-Larsen, Jonas Borch, Birger Lindberg Møller, Søren Bak. Convergent evolution in biosynthesis of cyanogenic defence compounds in plants and insects. Nature communications. 2011; 2(?):273. doi: 10.1038/ncomms1271. [PMID: 21505429]
  • M Guadalupe Rojas, Juan Alfredo Morales-Ramos. Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis. Journal of chemical ecology. 2010 Dec; 36(12):1354-62. doi: 10.1007/s10886-010-9872-5. [PMID: 20953678]
  • Adam Takos, Daniela Lai, Lisbeth Mikkelsen, Maher Abou Hachem, Dale Shelton, Mohammed Saddik Motawia, Carl Erik Olsen, Trevor L Wang, Cathie Martin, Fred Rook. Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism. The Plant cell. 2010 May; 22(5):1605-19. doi: 10.1105/tpc.109.073502. [PMID: 20453117]
  • Soad A L Bayoumi, Michael G Rowan, John R Beeching, Ian S Blagbrough. Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots. Phytochemistry. 2010 Apr; 71(5-6):598-604. doi: 10.1016/j.phytochem.2009.10.012. [PMID: 20137795]
  • Lotte Kolind-Hansen, Leon Brimer. The retail market for fresh cassava root tubers in the European Union (EU): the case of Copenhagen, Denmark--a chemical food safety issue?. Journal of the science of food and agriculture. 2010 Jan; 90(2):252-6. doi: 10.1002/jsfa.3804. [PMID: 20355039]
  • Somphit Sornyotha, Khin Lay Kyu, Khanok Ratanakhanokchai. An efficient treatment for detoxification process of cassava starch by plant cell wall-degrading enzymes. Journal of bioscience and bioengineering. 2010 Jan; 109(1):9-14. doi: 10.1016/j.jbiosc.2009.06.021. [PMID: 20129074]
  • Mika Zagrobelny, Karsten Scheibye-Alsing, Niels Bjerg Jensen, Birger Lindberg Møller, Jan Gorodkin, Søren Bak. 454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides. BMC genomics. 2009 Dec; 10(?):574. doi: 10.1186/1471-2164-10-574. [PMID: 19954531]
  • Daniel J Ballhorn, Stefanie Kautz, Martin Heil, Adrian D Hegeman. Cyanogenesis of wild lima bean (Phaseolus lunatus L.) is an efficient direct defence in nature. PloS one. 2009; 4(5):e5450. doi: ". [PMID: 19424497]
  • Vega García-Escudero, Ricardo Gargini. Autophagy induction as an efficient strategy to eradicate tumors. Autophagy. 2008 Oct; 4(7):923-5. doi: 10.4161/auto.6714. [PMID: 18716458]
  • Anne Vinther Morant, Nanna Bjarnholt, Mads Emil Kragh, Christian Hauge Kjaergaard, Kirsten Jørgensen, Suzanne Michelle Paquette, Markus Piotrowski, Anne Imberty, Carl Erik Olsen, Birger Lindberg Møller, Søren Bak. The beta-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus. Plant physiology. 2008 Jul; 147(3):1072-91. doi: 10.1104/pp.107.109512. [PMID: 18467457]
  • Nanna Bjarnholt, Mette Laegdsmand, Hans C B Hansen, Ole H Jacobsen, Birger Lindberg Møller. Leaching of cyanogenic glucosides and cyanide from white clover green manure. Chemosphere. 2008 Jun; 72(6):897-904. doi: 10.1016/j.chemosphere.2008.03.047. [PMID: 18472138]
  • Tetsuya Sakurai, Germán Plata, Fausto Rodríguez-Zapata, Motoaki Seki, Andrés Salcedo, Atsushi Toyoda, Atsushi Ishiwata, Joe Tohme, Yoshiyuki Sakaki, Kazuo Shinozaki, Manabu Ishitani. Sequencing analysis of 20,000 full-length cDNA clones from cassava reveals lineage specific expansions in gene families related to stress response. BMC plant biology. 2007 Dec; 7(?):66. doi: 10.1186/1471-2229-7-66. [PMID: 18096061]
  • Mika Zagrobelny, Søren Bak, Carl Erik Olsen, Birger Lindberg Møller. Intimate roles for cyanogenic glucosides in the life cycle of Zygaena filipendulae (Lepidoptera, Zygaenidae). Insect biochemistry and molecular biology. 2007 Nov; 37(11):1189-97. doi: 10.1016/j.ibmb.2007.07.008. [PMID: 17916505]
  • Christopher Avwoghokoghene Idibie, Hajierah Davids, Sunny Esayegbemu Iyuke. Cytotoxicity of purified cassava linamarin to a selected cancer cell lines. Bioprocess and biosystems engineering. 2007 Jul; 30(4):261-9. doi: 10.1007/s00449-007-0122-3. [PMID: 17566787]
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