2-Hydroxybenzyl alcohol (BioDeep_00000001211)

 

Secondary id: BioDeep_00000870089, BioDeep_00001867831

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


Salicyl alcohol, monosodium salt

化学式: C7H8O2 (124.0524)
中文名称: 2-羟基苄醇, 2-羟基苯甲醇
谱图信息: 最多检出来源 Homo sapiens(plant) 12.16%

分子结构信息

SMILES: C1=CC=C(C(=C1)CO)O
InChI: InChI=1S/C7H8O2/c8-5-6-3-1-2-4-7(6)9/h1-4,8-9H,5H2

描述信息

Salicyl alcohol, also known as saligenin or 2-hydroxybenzyl alcohol, is a member of the class of compounds known as benzyl alcohols. Benzyl alcohols are organic compounds containing the phenylmethanol substructure. Salicyl alcohol is soluble (in water) and a very weakly acidic compound (based on its pKa). Salicyl alcohol can be synthesized from phenol and benzyl alcohol. Salicyl alcohol can also be synthesized into salicin. Salicyl alcohol can be found in a number of food items such as red huckleberry, rye, jerusalem artichoke, and ceylon cinnamon, which makes salicyl alcohol a potential biomarker for the consumption of these food products. Salicyl alcohol (saligenin) is precursor of salicylic acid and is formed from salicin by enzymatic hydrolysis by Salicyl-alcohol beta-D-glucosyltransferase or by acid hydrolysis .
2-Hydroxybenzyl alcohol (CAS Number 90-01-7) is a stable light brown crystalline powder.
C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent
Salicyl alcohol is an intermediate for medicine, perfume, pesticide.
Salicyl alcohol is an intermediate for medicine, perfume, pesticide.

同义名列表

12 个代谢物同义名

Salicyl alcohol, monosodium salt; Salicyl alcohol, disodium salt; Salicyl alcohol, (ar)-isomer; 2-(Hydroxymethyl)phenol; 2-Hydroxybenzyl alcohol; O-Hydroxybenzyl alcohol; 2-Monomethylolphenol; 2-Methylol phenol; salicyl alcohol; Saligenin; Salicyl alcohol; 2-Hydroxybenzyl alcohol



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(1)

PlantCyc(1)

代谢反应

5 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(2)

PharmGKB(0)

12 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 7 ANXA5, CAT, DNM1L, KITLG, PTGS1, PTGS2, SRP54
Peripheral membrane protein 5 ANXA5, DNM1L, GBA1, PTGS1, PTGS2
Endosome membrane 1 ADRB2
Endoplasmic reticulum membrane 3 DNM1L, PTGS1, PTGS2
Nucleus 5 ADRB2, ERH, SRP54, TFDP2, ZNF79
cytosol 4 ANXA5, CAT, DNM1L, SRP54
trans-Golgi network 1 GBA1
nucleoplasm 2 CD2, TFDP2
RNA polymerase II transcription regulator complex 1 TFDP2
Cell membrane 5 ADRB2, CD2, KITLG, SLC26A4, TNF
lamellipodium 1 KITLG
Multi-pass membrane protein 3 ADRB2, SLC26A4, TPRA1
cell surface 2 CD2, TNF
Golgi apparatus 5 ADRB2, CD2, DNM1L, GBA1, PTGS1
lysosomal membrane 1 GBA1
neuronal cell body 1 TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 DNM1L
Lysosome 2 ADRB2, GBA1
endosome 1 ADRB2
plasma membrane 7 ADRB2, BCHE, CD2, KITLG, SLC26A4, TNF, TPRA1
synaptic vesicle membrane 1 DNM1L
Membrane 7 ADRB2, ANXA5, CAT, DNM1L, KITLG, SLC26A4, TPRA1
apical plasma membrane 2 ADRB2, SLC26A4
brush border 1 DNM1L
caveola 1 PTGS2
extracellular exosome 5 ANXA5, CAT, GBA1, PTGS1, SLC26A4
Lysosome membrane 1 GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 4 DNM1L, GBA1, PTGS2, SRP54
extracellular space 5 BCHE, IL10, IL3, KITLG, TNF
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 1 DNM1L
mitochondrion 2 CAT, DNM1L
protein-containing complex 4 CAT, CD2, DNM1L, PTGS2
intracellular membrane-bounded organelle 3 CAT, DNM1L, PTGS1
Microsome membrane 2 PTGS1, PTGS2
filopodium 1 KITLG
Single-pass type I membrane protein 2 CD2, KITLG
Secreted 4 BCHE, IL10, IL3, KITLG
extracellular region 9 ANXA5, BCHE, CAT, CD2, DNAH9, IL10, IL3, KITLG, TNF
cytoplasmic side of plasma membrane 1 CD2
Mitochondrion outer membrane 1 DNM1L
mitochondrial outer membrane 1 DNM1L
mitochondrial matrix 1 CAT
transcription regulator complex 1 TFDP2
motile cilium 1 DNAH9
photoreceptor outer segment 1 PTGS1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 DNM1L
external side of plasma membrane 3 ANXA5, CD2, TNF
midbody 1 ERH
Early endosome 1 ADRB2
Membrane, clathrin-coated pit 1 DNM1L
cell-cell junction 1 CD2
clathrin-coated pit 1 DNM1L
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 SLC26A4
Cell projection, lamellipodium 1 KITLG
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 KITLG
focal adhesion 2 ANXA5, CAT
microtubule 2 DNAH9, DNM1L
Peroxisome 2 CAT, DNM1L
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ANXA5
axoneme 1 DNAH9
nuclear speck 1 SRP54
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, filopodium 1 KITLG
receptor complex 1 ADRB2
Zymogen granule membrane 1 ANXA5
neuron projection 2 PTGS1, PTGS2
chromatin 1 TFDP2
phagocytic cup 1 TNF
mitotic spindle 1 TFDP2
cytoskeleton 1 KITLG
brush border membrane 1 SLC26A4
blood microparticle 1 BCHE
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAH9
Endomembrane system 2 DNM1L, PTGS1
Nucleus speckle 1 SRP54
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 2 BCHE, PTGS2
neuronal dense core vesicle 1 ADRB2
9+2 motile cilium 1 DNAH9
dynein complex 1 DNAH9
nuclear envelope lumen 1 BCHE
methylosome 1 ERH
[Isoform 2]: Cytoplasm 1 KITLG
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 ADRB2
signal recognition particle 1 SRP54
signal recognition particle, endoplasmic reticulum targeting 1 SRP54
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
endothelial microparticle 1 ANXA5
outer dynein arm 1 DNAH9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
distal portion of axoneme 1 DNAH9


文献列表

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Monika Untergehrer, Josef Kiermaier, Susanne Reintjes, Jörg Heilmann, Guido Jürgenliemk. Identification of phase-II metabolites from human serum samples after oral intake of a willow bark extract. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Apr; 57(?):396-402. doi: 10.1016/j.phymed.2018.11.003. [PMID: 30849676]
  • Wataru Nabeyama, Kenji Ishihara, Hyun Seung Ban, Hiroshi Wada, Hiroyuki Nakamura. Discovery of (2-aminophenyl)methanol as a new molecular chaperone that rescues the localization of P123S mutant pendrin stably expressed in HEK293 cells. Bioorganic & medicinal chemistry. 2017 05; 25(9):2601-2608. doi: 10.1016/j.bmc.2017.03.024. [PMID: 28341401]
  • 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]
  • Mariya S Liyasova, Lawrence M Schopfer, Oksana Lockridge. Cresyl saligenin phosphate makes multiple adducts on free histidine, but does not form an adduct on histidine 438 of human butyrylcholinesterase. Chemico-biological interactions. 2013 Mar; 203(1):103-7. doi: 10.1016/j.cbi.2012.07.006. [PMID: 22898212]
  • G Ulrich-Merzenich, O Kelber, A Koptina, A Freischmidt, J Heilmann, J Müller, H Zeitler, M F Seidel, M Ludwig, E U Heinrich, H Winterhoff. Novel neurological and immunological targets for salicylate-based phytopharmaceuticals and for the anti-depressant imipramine. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2012 Jul; 19(10):930-9. doi: 10.1016/j.phymed.2012.05.004. [PMID: 22743246]
  • Keisuke Morita, Hisanori Imura. Substoichiometric isotope dilution mass spectrometry of boron by the ion-pair extraction with halogenated salicyl alcohol derivatives and a quaternary ammonium salt. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2012; 28(3):243-9. doi: 10.2116/analsci.28.243. [PMID: 22451364]
  • Mariya Liyasova, Bin Li, Lawrence M Schopfer, Florian Nachon, Patrick Masson, Clement E Furlong, Oksana Lockridge. Exposure to tri-o-cresyl phosphate detected in jet airplane passengers. Toxicology and applied pharmacology. 2011 Nov; 256(3):337-47. doi: 10.1016/j.taap.2011.06.016. [PMID: 21723309]
  • G Andreas Boeckler, Jonathan Gershenzon, Sybille B Unsicker. Phenolic glycosides of the Salicaceae and their role as anti-herbivore defenses. Phytochemistry. 2011 Sep; 72(13):1497-509. doi: 10.1016/j.phytochem.2011.01.038. [PMID: 21376356]
  • Susanne Knuth, Helmut Schübel, Martin Hellemann, Guido Jürgenliemk. Catechol, a bioactive degradation product of salicortin, reduces TNF-α induced ICAM-1 expression in human endothelial cells. Planta medica. 2011 Jul; 77(10):1024-6. doi: 10.1055/s-0030-1270722. [PMID: 21305449]
  • Karla Tolzin-Banasch, Enkhmaa Dagvadorj, Ulrike Sammer, Maritta Kunert, Roy Kirsch, Kerstin Ploss, Jacques M Pasteels, Wilhelm Boland. Glucose and glucose esters in the larval secretion of Chrysomela lapponica; selectivity of the glucoside import system from host plant leaves. Journal of chemical ecology. 2011 Feb; 37(2):195-204. doi: 10.1007/s10886-011-9913-8. [PMID: 21301937]
  • Thomas Louveau, Celine Leitao, Sol Green, Cyril Hamiaux, Benoît van der Rest, Odile Dechy-Cabaret, Ross G Atkinson, Christian Chervin. Predicting the substrate specificity of a glycosyltransferase implicated in the production of phenolic volatiles in tomato fruit. The FEBS journal. 2011 Jan; 278(2):390-400. doi: 10.1111/j.1742-4658.2010.07962.x. [PMID: 21166996]
  • Raquel González-Fernández, Elena Prats, Jesús V Jorrín-Novo. Proteomics of plant pathogenic fungi. Journal of biomedicine & biotechnology. 2010; 2010(?):932527. doi: 10.1155/2010/932527. [PMID: 20589070]
  • Raja S Payyavula, Benjamin A Babst, Matthew P Nelsen, Scott A Harding, Chung-Jui Tsai. Glycosylation-mediated phenylpropanoid partitioning in Populus tremuloides cell cultures. BMC plant biology. 2009 Dec; 9(?):151. doi: 10.1186/1471-2229-9-151. [PMID: 20040108]
  • Surajdevprakash B Dhiman, Jayashree P Kamat, Devidas B Naik. Antioxidant activity and free radical scavenging reactions of hydroxybenzyl alcohols. Biochemical and pulse radiolysis studies. Chemico-biological interactions. 2009 Dec; 182(2-3):119-27. doi: 10.1016/j.cbi.2009.07.025. [PMID: 19665455]
  • Elodie Descamps, Maud Petrault-Laprais, Pierre Maurois, Nicole Pages, Pierre Bac, Régis Bordet, Joseph Vamecq. Experimental stroke protection induced by 4-hydroxybenzyl alcohol is cancelled by bacitracin. Neuroscience research. 2009 Jun; 64(2):137-42. doi: 10.1016/j.neures.2009.02.005. [PMID: 19428693]
  • Carmen Michalski, Hoda Mohagheghi, Manfred Nimtz, Jacques Pasteels, Dietrich Ober. Salicyl alcohol oxidase of the chemical defense secretion of two chrysomelid leaf beetles. Molecular and functional characterization of two new members of the glucose-methanol-choline oxidoreductase gene family. The Journal of biological chemistry. 2008 Jul; 283(28):19219-28. doi: 10.1074/jbc.m802236200. [PMID: 18482980]
  • Hassan A N El-Fawal, Wilfred C McCain. Antibodies to neural proteins in organophosphorus-induced delayed neuropathy (OPIDN) and its amelioration. Neurotoxicology and teratology. 2008 May; 30(3):161-6. doi: 10.1016/j.ntt.2008.01.005. [PMID: 18353611]
  • Hany A El-Shemy, Ahmed M Aboul-Enein, Khalid Mostafa Aboul-Enein, Kounosuke Fujita. Willow leaves' extracts contain anti-tumor agents effective against three cell types. PloS one. 2007 Jan; 2(1):e178. doi: 10.1371/journal.pone.0000178. [PMID: 17264881]
  • Katarina Hostanska, Guido Jürgenliemk, Gudrun Abel, Adolf Nahrstedt, Reinhard Saller. Willow bark extract (BNO1455) and its fractions suppress growth and induce apoptosis in human colon and lung cancer cells. Cancer detection and prevention. 2007; 31(2):129-39. doi: 10.1016/j.cdp.2007.03.001. [PMID: 17418981]
  • Swati J Modi, William R LaCourse. Monitoring carbohydrate enzymatic reactions by quantitative in vitro microdialysis. Journal of chromatography. A. 2006 Jun; 1118(1):125-33. doi: 10.1016/j.chroma.2006.02.045. [PMID: 16546198]
  • Fernando A Genta, Rod J Dillon, Walter R Terra, Clélia Ferreira. Potential role for gut microbiota in cell wall digestion and glucoside detoxification in Tenebrio molitor larvae. Journal of insect physiology. 2006 Jun; 52(6):593-601. doi: 10.1016/j.jinsphys.2006.02.007. [PMID: 16600286]
  • Kristiina Aalto-Korte, Jarmo Välimaa, Maj-Len Henriks-Eckerman, Riitta Jolanki. Allergic contact dermatitis from salicyl alcohol and salicylaldehyde in aspen bark (Populus tremula). Contact dermatitis. 2005 Feb; 52(2):93-5. doi: 10.1111/j.0105-1873.2005.00506.x. [PMID: 15725287]
  • Stuart McLean, Sue Brandon, Noel W Davies, Rebecca Boyle, William J Foley, Ben Moore, Georgia J Pass. Glucuronuria in the koala. Journal of chemical ecology. 2003 Jun; 29(6):1465-77. doi: 10.1023/a:1024273722192. [PMID: 12918928]
  • Teruaki Akao, Tetsuro Yoshino, Kyoich Kobashi, Masao Hattori. Evaluation of salicin as an antipyretic prodrug that does not cause gastric injury. Planta medica. 2002 Aug; 68(8):714-8. doi: 10.1055/s-2002-33792. [PMID: 12221594]
  • A Itoh, T Tanahashi, N Nagakura, K Inoue, H Kuwajima, H X Wu. Glycosides of benzyl and salicyl alcohols from Alangium chinense. Chemical & pharmaceutical bulletin. 2001 Oct; 49(10):1343-5. doi: 10.1248/cpb.49.1343. [PMID: 11605667]
  • S McLean, G J Pass, W J Foley, S Brandon, N W Davies. Does excretion of secondary metabolites always involve a measurable metabolic cost? Fate of plant antifeedant salicin in common brushtail possum, Trichosurus vulpecula. Journal of chemical ecology. 2001 Jun; 27(6):1077-89. doi: 10.1023/a:1010303726439. [PMID: 11504015]
  • T Estlander, R Jolanki, K Alanko, L Kanerva. Occupational allergic contact dermatitis caused by wood dusts. Contact dermatitis. 2001 Apr; 44(4):213-7. doi: 10.1034/j.1600-0536.2001.044004213.x. [PMID: 11260236]
  • M Sakurai, M Ohsako, M Nagano, C Nakamura, O Tsuzuki, M Ichikawa, Y Matsumoto. [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1996 Aug; 116(8):630-8. doi: 10.1248/yakushi1947.116.8_630. [PMID: 8831264]
  • W C McCain, D M Flaherty, L Correll, B Jortner, M Ehrich. Catecholamine concentrations and contractile responses of isolated vessels from hens treated with cyclic phenyl saligenin phosphate or paraoxon in the presence or absence of verapamil. Journal of toxicology and environmental health. 1996 Jul; 48(4):397-411. doi: 10.1080/009841096161276. [PMID: 8691509]
  • A Mentzschel, S Vamvakas, W Dekant, D Henschler. DNA adduct formation in Salmonella typhimurium, cultured liver cells and in Fischer 344 rats treated with o-tolyl phosphates and their metabolites. Carcinogenesis. 1993 Oct; 14(10):2039-43. doi: 10.1093/carcin/14.10.2039. [PMID: 8222051]
  • Y Y Mo, D C Gross. Plant signal molecules activate the syrB gene, which is required for syringomycin production by Pseudomonas syringae pv. syringae. Journal of bacteriology. 1991 Sep; 173(18):5784-92. doi: 10.1128/jb.173.18.5784-5792.1991. [PMID: 1885550]
  • J L Rosner, M Aumercier. Potentiation by salicylate and salicyl alcohol of cadmium toxicity and accumulation in Escherichia coli. Antimicrobial agents and chemotherapy. 1990 Dec; 34(12):2402-6. doi: 10.1128/aac.34.12.2402. [PMID: 2088194]
  • M Aumercier, D M Murray, J L Rosner. Potentiation of susceptibility to aminoglycosides by salicylate in Escherichia coli. Antimicrobial agents and chemotherapy. 1990 May; 34(5):786-91. doi: 10.1128/aac.34.5.786. [PMID: 2193619]
  • S Tsuji, K Nakagawa, T Fukushima. Genetically controlled quantitative variation of ornithine transcarbamylase in the chick kidney. Biochemical genetics. 1983 Oct; 21(9-10):857-69. doi: 10.1007/bf00483945. [PMID: 6419722]
  • H H Borden, R W Harris, W E Mosher. A waterborne outbreak of gastroenteritis in western New York State. American journal of public health and the nation's health. 1970 Feb; 60(2):283-8. doi: 10.2105/ajph.60.2.283. [PMID: 5460971]
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