Salicin (BioDeep_00000000284)

 

Secondary id: BioDeep_00000398593

human metabolite PANOMIX_OTCML-2023 Chemicals and Drugs natural product


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 (286.1052)
中文名称: D(-)-水杨苷, 水杨苷
谱图信息: 最多检出来源 Viridiplantae(plant) 25.82%

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as salicoside or delta-salicin, is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue.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Salicin is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue.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

79 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; Salicin; Salicin



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(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)

237 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 6 CAT, FABP4, HSPD1, PIK3CA, PTGS1, PTGS2
Golgi apparatus, trans-Golgi network membrane 1 LRBA
Peripheral membrane protein 4 GBA1, GORASP1, PTGS1, PTGS2
Endoplasmic reticulum membrane 3 LRBA, PTGS1, PTGS2
Nucleus 3 FABP4, GABPA, PLCZ1
cytosol 6 CAT, FABP4, HSPD1, LRBA, PIK3CA, PLCZ1
trans-Golgi network 2 GBA1, TAS2R16
nucleoplasm 2 GABPA, PLCZ1
Cell membrane 3 LRBA, TAS2R16, TNF
Cytoplasmic side 1 GORASP1
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 TAS2R16
Golgi apparatus membrane 1 GORASP1
cell surface 2 HSPD1, TNF
Golgi apparatus 5 GBA1, GORASP1, LRBA, PTGS1, TAS1R3
Golgi membrane 1 GORASP1
lysosomal membrane 3 GAA, GBA1, LRBA
mitochondrial inner membrane 1 HSPD1
neuronal cell body 1 TNF
Lysosome 2 GAA, GBA1
plasma membrane 7 GAA, HSPD1, LRBA, PIK3CA, TAS1R3, TAS2R16, TNF
Membrane 8 CAT, CLYBL, GAA, GUSB, HSPD1, LRBA, TAS1R3, TAS2R16
caveola 1 PTGS2
extracellular exosome 7 CAT, FABP4, GAA, GBA1, GUSB, HSPD1, PTGS1
Lysosome membrane 3 GAA, GBA1, LRBA
Lumenal side 1 GBA1
endoplasmic reticulum 3 GBA1, PTGS2, TAS2R16
extracellular space 6 GH1, GUSB, HSPD1, IL10, IL6, TNF
lysosomal lumen 3 GAA, GBA1, GUSB
perinuclear region of cytoplasm 2 PIK3CA, PLCZ1
intercalated disc 1 PIK3CA
mitochondrion 3 CAT, CLYBL, HSPD1
protein-containing complex 3 CAT, HSPD1, PTGS2
intracellular membrane-bounded organelle 4 CAT, GAA, GUSB, PTGS1
Microsome membrane 2 PTGS1, PTGS2
pronucleus 1 PLCZ1
Secreted 4 GAA, GH1, IL10, IL6
extracellular region 7 CAT, GAA, GH1, GUSB, IL10, IL6, TNF
Single-pass membrane protein 1 LRBA
mitochondrial matrix 2 CAT, HSPD1
photoreceptor outer segment 1 PTGS1
external side of plasma membrane 2 TAS2R16, TNF
nucleolus 1 PLCZ1
Early endosome 1 HSPD1
clathrin-coated pit 1 HSPD1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 PLCZ1
Membrane raft 1 TNF
focal adhesion 1 CAT
cis-Golgi network 1 GORASP1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 HSPD1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 2 PTGS1, PTGS2
chromatin 1 GABPA
phagocytic cup 1 TNF
sperm midpiece 1 HSPD1
Endomembrane system 1 PTGS1
endosome lumen 1 GH1
Lipid droplet 1 FABP4
tertiary granule membrane 1 GAA
sperm plasma membrane 1 HSPD1
lipopolysaccharide receptor complex 1 HSPD1
ficolin-1-rich granule lumen 2 CAT, GUSB
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 2 IL6, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
azurophil granule membrane 1 GAA
azurophil granule lumen 1 GUSB
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
ficolin-1-rich granule membrane 1 GAA
coated vesicle 1 HSPD1
growth hormone receptor complex 1 GH1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
sperm head 1 PLCZ1
interleukin-6 receptor complex 1 IL6
autolysosome lumen 1 GAA
migrasome 1 HSPD1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
sweet taste receptor complex 1 TAS1R3


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]
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  • 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]
  • Hellen A Oketch-Rabah, Robin J Marles, Scott A Jordan, Tieraona Low Dog. United States Pharmacopeia Safety Review of Willow Bark. Planta medica. 2019 Nov; 85(16):1192-1202. doi: 10.1055/a-1007-5206. [PMID: 31604354]
  • Keqiang Gao, Fan Gao, Liping Du, Chuanjiang He, Hao Wan, Ping Wang. Integrated olfaction, gustation and toxicity detection by a versatile bioengineered cell-based biomimetic sensor. Bioelectrochemistry (Amsterdam, Netherlands). 2019 Aug; 128(?):1-8. doi: 10.1016/j.bioelechem.2019.02.009. [PMID: 30861388]
  • Lydia Schmidt, Natalie Wielsch, Ding Wang, Wilhelm Boland, Antje Burse. Tissue-specific profiling of membrane proteins in the salicin sequestering juveniles of the herbivorous leaf beetle, Chrysomela populi. Insect biochemistry and molecular biology. 2019 06; 109(?):81-91. doi: 10.1016/j.ibmb.2019.03.009. [PMID: 30922827]
  • Thomas Fabisch, Jonathan Gershenzon, Sybille B Unsicker. Specificity of Herbivore Defense Responses in a Woody Plant, Black Poplar (Populus nigra). Journal of chemical ecology. 2019 Feb; 45(2):162-177. doi: 10.1007/s10886-019-01050-y. [PMID: 30788656]
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  • 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]
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  • 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]
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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]
  • Atsushi Ishikado, Yoko Sono, Motonobu Matsumoto, Stacey Robida-Stubbs, Aya Okuno, Masashi Goto, George L King, T Keith Blackwell, Taketoshi Makino. Willow bark extract increases antioxidant enzymes and reduces oxidative stress through activation of Nrf2 in vascular endothelial cells and Caenorhabditis elegans. Free radical biology & medicine. 2013 Dec; 65(?):1506-1515. doi: 10.1016/j.freeradbiomed.2012.12.006. [PMID: 23277146]
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