Salicin (BioDeep_00000000284)

 

Secondary id: BioDeep_00000398593

human metabolite PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside, Salicoside, Salicyl alcohol glucoside, Saligenin beta-D-glucoside

化学式: C13H18O7 (286.10524780000003)
中文名称: D(-)-水杨苷, 水杨苷
谱图信息: 最多检出来源 Viridiplantae(plant) 0.26%

分子结构信息

SMILES: C1=CC=C(C(=C1)CO)OC2C(C(C(C(O2)CO)O)O)O
InChI: InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2

描述信息

Salicin, also known as salicoside or delta-salicin, is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a prodrug, an antipyretic, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is an aryl beta-D-glucoside, an aromatic primary alcohol and a member of benzyl alcohols. It derives from a salicyl alcohol. Salicin belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Salicin exists in all living organisms, ranging from bacteria to humans. Salicin is a bitter tasting compound.
Salicin is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a prodrug, an antipyretic, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is an aryl beta-D-glucoside, an aromatic primary alcohol and a member of benzyl alcohols. It is functionally related to a salicyl alcohol.
Salicin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Salicin is a natural product found in Salix candida, Populus tremula, and other organisms with data available.
Salicin is an alcoholic β-glycoside that contains D-glucose. Salicin is an anti-inflammatory agent that is produced from willow bark. Salicin is closely related in chemical make-up to aspirin and has a very similar action in the human body. When consumed by humans, Salicin is metabolized into salicylic acid. [HMDB]
An aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue.
D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent
D002491 - Central Nervous System Agents > D000700 - Analgesics
D000893 - Anti-Inflammatory Agents
D004791 - Enzyme Inhibitors
Salicin is a natural COX inhibitor.
Salicin is a natural COX inhibitor.

同义名列表

77 个代谢物同义名

2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside, Salicoside, Salicyl alcohol glucoside, Saligenin beta-D-glucoside; (2S,4S,5S,3R,6R)-6-(hydroxymethyl)-2-[2-(hydroxymethyl)phenoxy]-2H-3,4,5,6-tet rahydropyran-3,4,5-triol; (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-(hydroxymethyl)-phenoxy)tetrahydro-2H-pyran-3,4,5-triol; (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol; WURCS=2.0/1,1,0/[a2122h-1b_1-5_1*O(C^ZC^ZC^ZC^ZC^ZC^E$3)/4CO]/1/; D-Salicin, United States Pharmacopeia (USP) Reference Standard; Salicin, European Pharmacopoeia (EP) Reference Standard; 2-(hydroxymethyl)phenyl-O-beta-D-glucopyranoside; 2-(Hydroxymethyl)phenyl-.beta.-d-glucopyranoside; 2-(Hydroxymethyl)-phenyl-beta-D-glucopyranoside; beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl; o-(Hydroxymethyl)phenyl beta-D-glucopyranoside; 2-(Hydroxymethyl)phenyl beta-D-glucopyranoside; 2-(Hydroxymethyl)phenyl-beta-d-glucopyranoside; 2-(Hydroxymethyl)phenyl-O-β-D-glucopyranoside; 2(hydroxymethyl)phenyl-beta-D-glucopyranoside; 2-(Hydroxymethyl)phenyl-O-b-D-glucopyranoside; B-D-Glucopyranoside, 2-(hydroxymethyl)phenyl; alpha-Hydroxy-o-tolyl beta-D-glucopyranoside; O-(Hydroxymethyl)phenyl b-D-glucopyranoside; 2-(Hydroxymethyl)phenyl-β-D-glucopyranoside; 2-(Hydroxymethyl)phenyl-b-D-glucopyranoside; O-(Hydroxymethyl)phenyl β-D-glucopyranoside; 2(Hydroxymethyl)phenyl-b-D-glucopyranoside; 2(Hydroxymethyl)phenyl-β-D-glucopyranoside; Benzyl alcohol, o-hydroxy-, o-glucoside; 2-(Hydroxymethyl)phenyl hexopyranoside; EAD32BE1-198E-432C-9F44-DC0DC9A3305B; Saligenin-beta-delta-glucopyranoside; Saligenin beta-delta-glucopyranoside; D-(-)-Salicin, analytical standard; SALICYL ALCOHOL GLUCOSIDE [WHO-DD]; Saligenin beta-D-glucopyranoside; Saligenin-beta-D-glucopyranoside; Salicin (Salicoside, Salicine); Saligenin-b-D-glucopyranoside; Saligenin β-D-glucopyranoside; Saligenin b-D-glucopyranoside; NGFMICBWJRZIBI-UJPOAAIJSA-N; D-(-)-Salicin, >=99\\% (GC); salicyl alcohol glucoside; D-()-Salicin;Salicoside; Saligenin glucoside; D-SALICIN [USP-RS]; Salicin (6CI,8CI); Spectrum3_000948; SALICINUM [HPUS]; Spectrum2_000756; Spectrum5_000971; Spectrum4_001058; SALICIN [INCI]; D-(?)-Salicin; delta-Salicin; D-(-)-Salicin; Salicin [USP]; DivK1c_000030; MEGxp0_000685; ACon1_000373; D(-)-Salicin; D-()-Salicin; KBio3_002016; KBio2_001710; SALICIN [MI]; KBio2_004278; KBio1_000030; KBio2_006846; IDI1_000030; Salicoside; D-Salicin; Salicinum; AI3-19099; C13H18O7; Salicine; Salicin; SA0; D-(-)-Salicin;Salicoside



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

53 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

  • Yashika Gandhi, Hemant Rawat, Daljeet Singh Dhanjal, Vijay Kumar, Vaibhav Charde, Hemant Soni, Sujeet K Mishra, Gagandeep Singh, Simranjeet Singh, Preeti Sharma, Santosh K Shakya, C V Narsimhaji, Ajay K Meena, Arjun Singh, Ravindra Singh, Naryanam Srikanth, Rabinarayan Acharya. A Comparative Analysis of Phytochemicals, Metal Ions, Volatile Metabolites in Heart Wood, Stem Bark and Leaves of Salix alba L. along with in Vitro Antioxidant, Antacid, Antimicrobial Activities for Sake of Environment Conservation by Substitution of Stem Bark With Leaf. Chemistry & biodiversity. 2023 Dec; 20(12):e202301234. doi: 10.1002/cbdv.202301234. [PMID: 37867394]
  • Hee Jung Kim, Da Eun Lee, Eon Chung Park, Moon-Jin Ra, Sang-Mi Jung, Jeong-Nam Yu, Sung Hee Um, Ki Hyun Kim. Anti-Adipogenic Effects of Salicortin from the Twigs of Weeping Willow (Salix pseudolasiogyne) in 3T3-L1 Cells. Molecules (Basel, Switzerland). 2022 Oct; 27(20):. doi: 10.3390/molecules27206954. [PMID: 36296558]
  • Nguyen Phan Khoi Le, Corinna Herz, João Victor Dutra Gomes, Nadja Förster, Kyriaki Antoniadou, Verena Karolin Mittermeier-Kleßinger, Inga Mewis, Corinna Dawid, Christian Ulrichs, Evelyn Lamy. Comparative Anti-Inflammatory Effects of Salix Cortex Extracts and Acetylsalicylic Acid in SARS-CoV-2 Peptide and LPS-Activated Human In Vitro Systems. International journal of molecular sciences. 2021 Jun; 22(13):. doi: 10.3390/ijms22136766. [PMID: 34201817]
  • Kartika Vashishtha, S Mahadevan. Catabolism of aromatic β-glucosides by bacteria can lead to antibiotics resistance. Archives of microbiology. 2020 Aug; 202(6):1301-1315. doi: 10.1007/s00203-020-01836-9. [PMID: 32130434]
  • Nathalie D Lackus, Andrea Müller, Tabea D U Kröber, Michael Reichelt, Axel Schmidt, Yoko Nakamura, Christian Paetz, Katrin Luck, Richard L Lindroth, C Peter Constabel, Sybille B Unsicker, Jonathan Gershenzon, Tobias G Köllner. The Occurrence of Sulfated Salicinoids in Poplar and Their Formation by Sulfotransferase1. Plant physiology. 2020 05; 183(1):137-151. doi: 10.1104/pp.19.01447. [PMID: 32098786]
  • Jane L Ward, Yanqi Wu, Claudia Harflett, Hannah Onafuye, Delia Corol, Charlotte Lomax, William J Macalpine, Jindrich Cinatl, Mark N Wass, Martin Michaelis, Michael H Beale. Miyabeacin: A new cyclodimer presents a potential role for willow in cancer therapy. Scientific reports. 2020 04; 10(1):6477. doi: 10.1038/s41598-020-63349-1. [PMID: 32296088]
  • Christin Fellenberg, Oliver Corea, Lok-Hang Yan, Finn Archinuk, Eerik-Mikael Piirtola, Harley Gordon, Michael Reichelt, Wolfgang Brandt, Jeremy Wulff, Jürgen Ehlting, C Peter Constabel. Discovery of salicyl benzoate UDP-glycosyltransferase, a central enzyme in poplar salicinoid phenolic glycoside biosynthesis. The Plant journal : for cell and molecular biology. 2020 04; 102(1):99-115. doi: 10.1111/tpj.14615. [PMID: 31736216]
  • Manrong Yu, Hui Chen, Pan Liu, Mei Yang, Leqin Zou, Dingfu Xiao. Antioxidant Function and Metabolomics Study in Mice after Dietary Supplementation with Methionine. BioMed research international. 2020; 2020(?):9494528. doi: 10.1155/2020/9494528. [PMID: 33145362]
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  • Vieri Piazzini, Elisabetta Bigagli, Cristina Luceri, Anna Rita Bilia, Maria Camilla Bergonzi. Enhanced Solubility and Permeability of Salicis cortex Extract by Formulating as a Microemulsion. Planta medica. 2018 Aug; 84(12-13):976-984. doi: 10.1055/a-0611-6203. [PMID: 29689586]
  • Giulio Del Popolo, Federico Nelli. Recurrent bacterial symptomatic cystitis: A pilot study on a new natural option for treatment. Archivio italiano di urologia, andrologia : organo ufficiale [di] Societa italiana di ecografia urologica e nefrologica. 2018 Jun; 90(2):101-103. doi: 10.4081/aiua.2018.2.101. [PMID: 29974728]
  • Ke-Feng Zhai, Hong Duan, Ghulam Jilany Khan, Hui Xu, Fang-Kai Han, Wen-Gen Cao, Gui-Zhen Gao, Ling-Ling Shan, Zhao-Jun Wei. Salicin from Alangium chinense Ameliorates Rheumatoid Arthritis by Modulating the Nrf2-HO-1-ROS Pathways. Journal of agricultural and food chemistry. 2018 Jun; 66(24):6073-6082. doi: 10.1021/acs.jafc.8b02241. [PMID: 29852739]
  • Clarice Noleto-Dias, Jane L Ward, Alice Bellisai, Charlotte Lomax, Michael H Beale. Salicin-7-sulfate: A new salicinoid from willow and implications for herbal medicine. Fitoterapia. 2018 Jun; 127(?):166-172. doi: 10.1016/j.fitote.2018.02.009. [PMID: 29447984]
  • Elizabeth Vaca, Claire Behrens, Tiju Theccanat, Jun-Yong Choe, John V Dean. Mechanistic differences in the uptake of salicylic acid glucose conjugates by vacuolar membrane-enriched vesicles isolated from Arabidopsis thaliana. Physiologia plantarum. 2017 Nov; 161(3):322-338. doi: 10.1111/ppl.12602. [PMID: 28665551]
  • Anup Kumar Singh, Sarma Rajeev Kumar, Varun Dwivedi, Avanish Rai, Shaifali Pal, Ajit K Shasany, Dinesh A Nagegowda. A WRKY transcription factor from Withania somnifera regulates triterpenoid withanolide accumulation and biotic stress tolerance through modulation of phytosterol and defense pathways. The New phytologist. 2017 Aug; 215(3):1115-1131. doi: 10.1111/nph.14663. [PMID: 28649699]
  • Garcia Gonzalez Jessica, Garcia Lorenzana Mario, Zamilpa Alejandro, Almanza Perez Julio Cesar, Jasso Villagomez E Ivan, Roman Ramos Ruben, Alarcon-Aguilar Francisco Javier. CHEMICAL CHARACTERIZATION OF A HYPOGLYCEMIC EXTRACT FROM CUCURBITA FICIFOLIA BOUCHE THAT INDUCES LIVER GLYCOGEN ACCUMULATION IN DIABETIC MICE. African journal of traditional, complementary, and alternative medicines : AJTCAM. 2017; 14(3):218-230. doi: 10.21010/ajtcam.v14i3.24. [PMID: 28480434]
  • G Andreas Boeckler, Christian Paetz, Peter Feibicke, Jonathan Gershenzon, Sybille B Unsicker. Metabolism of poplar salicinoids by the generalist herbivore Lymantria dispar (Lepidoptera). Insect biochemistry and molecular biology. 2016 11; 78(?):39-49. doi: 10.1016/j.ibmb.2016.08.001. [PMID: 27503687]
  • Yanqi Wu, Darja Dobermann, Michael H Beale, Jane L Ward. Acutifoliside, a novel benzoic acid glycoside from Salix acutifolia. Natural product research. 2016 Aug; 30(15):1731-9. doi: 10.1080/14786419.2015.1137571. [PMID: 26820172]
  • Lijuan Wang, Liangjian Qu, Liwei Zhang, Jianjun Hu, Fang Tang, Mengzhu Lu. Metabolic Responses of Poplar to Apripona germari (Hope) as Revealed by Metabolite Profiling. International journal of molecular sciences. 2016 Jun; 17(5):. doi: 10.3390/ijms17060923. [PMID: 27331808]
  • Chung Sub Kim, Lalita Subedi, Kyoung Jin Park, Sun Yeou Kim, Sang Un Choi, Ki Hyun Kim, Kang Ro Lee. Salicin derivatives from Salix glandulosa and their biological activities. Fitoterapia. 2015 Oct; 106(?):147-52. doi: 10.1016/j.fitote.2015.08.013. [PMID: 26344424]
  • Mohd Shara, Sidney J Stohs. Efficacy and Safety of White Willow Bark (Salix alba) Extracts. Phytotherapy research : PTR. 2015 Aug; 29(8):1112-6. doi: 10.1002/ptr.5377. [PMID: 25997859]
  • Russell J Chedgy, Tobias G Köllner, C Peter Constabel. Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis. Phytochemistry. 2015 May; 113(?):149-59. doi: 10.1016/j.phytochem.2014.10.018. [PMID: 25561400]
  • Wei Wei, Kasimu Rena, Xiu-Wei Yang. New salicin derivatives from the leaves of Populus euphratica. Journal of Asian natural products research. 2015 May; 17(5):491-6. doi: 10.1080/10286020.2015.1028920. [PMID: 25903097]
  • Parisa Zangoui, Kartika Vashishtha, Subramony Mahadevan. Evolution of aromatic β-glucoside utilization by successive mutational steps in Escherichia coli. Journal of bacteriology. 2015 Feb; 197(4):710-6. doi: 10.1128/jb.02185-14. [PMID: 25448815]
  • Nadine Austel, Andreas Reinecke, Christer Björkman, Monika Hilker, Torsten Meiners. Phenotypic plasticity in a willow leaf beetle depends on host plant species: release and recognition of beetle odors. Chemical senses. 2015 Feb; 40(2):109-24. doi: 10.1093/chemse/bju065. [PMID: 25537016]
  • Chang-Seok Kong, Ka-Hyun Kim, Jae-Sun Choi, Ja-Eun Kim, Chan Park, Joo-Won Jeong. Salicin, an extract from white willow bark, inhibits angiogenesis by blocking the ROS-ERK pathways. Phytotherapy research : PTR. 2014 Aug; 28(8):1246-51. doi: 10.1002/ptr.5126. [PMID: 24535656]
  • Fengli Chen, Kailin Mo, Zhaizhi Liu, Fengjian Yang, Kexin Hou, Shuangyang Li, Yuangang Zu, Lei Yang. Ionic liquid-based vacuum microwave-assisted extraction followed by macroporous resin enrichment for the separation of the three glycosides salicin, hyperin and rutin from Populus bark. Molecules (Basel, Switzerland). 2014 Jul; 19(7):9689-711. doi: 10.3390/molecules19079689. [PMID: 25004075]
  • Tara Joy Massad, Susan E Trumbore, Gantsetseg Ganbat, Michael Reichelt, Sybille Unsicker, Andreas Boeckler, Gerd Gleixner, Jonathan Gershenzon, Steffen Ruehlow. An optimal defense strategy for phenolic glycoside production in Populus trichocarpa--isotope labeling demonstrates secondary metabolite production in growing leaves. The New phytologist. 2014 Jul; 203(2):607-619. doi: 10.1111/nph.12811. [PMID: 24739022]
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  • Nirmal Verma, Ravi Verma, Reena Kumari, Raju Ranjha, Jaishree Paul. Effect of salicin on gut inflammation and on selected groups of gut microbiota in dextran sodium sulfate induced mouse model of colitis. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2014 Feb; 63(2):161-9. doi: 10.1007/s00011-013-0685-1. [PMID: 24240229]
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