Azelaic Acid (BioDeep_00000400099)

Main id: BioDeep_00000000146

 

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


Azelaic Acid

化学式: C9H16O4 (188.1048536)
中文名称: 壬二酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.42%

分子结构信息

SMILES: C(CCCC(=O)O)CCCC(=O)O
InChI: InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)

描述信息

D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use
C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent
D000970 - Antineoplastic Agents
D003879 - Dermatologic Agents
Annotation level-2
Azelaic acid is a nine-carbon dicarboxylic acid. Azelaic acid has antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis through inhibition of microbial cellular prorein synthesis. Azelaic acid has hypopigmentation action resulting from its ability to scavenge free radicals[1][2].
Azelaic acid is a nine-carbon dicarboxylic acid. Azelaic acid has antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis through inhibition of microbial cellular prorein synthesis. Azelaic acid has hypopigmentation action resulting from its ability to scavenge free radicals[1][2].

同义名列表

4 个代谢物同义名

Azelaic Acid; Nonanedioic acid; Azelaic acid; Azelaic acid



数据库引用编号

60 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)

123 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

  • Sara Álvarez-Rodríguez, Fabrizio Araniti, Marta Teijeira, Manuel J Reigosa, Adela M Sánchez-Moreiras. Azelaic acid can efficiently compete for the auxin binding site TIR1, altering auxin polar transport, gravitropic response, and root growth and architecture in Arabidopsisthaliana roots. Plant physiology and biochemistry : PPB. 2024 May; 210(?):108592. doi: 10.1016/j.plaphy.2024.108592. [PMID: 38569422]
  • Ahmed A Shibl, Michael A Ochsenkühn, Amin R Mohamed, Ashley Isaac, Lisa S Y Coe, Yejie Yun, Grzegorz Skrzypek, Jean-Baptiste Raina, Justin R Seymour, Ahmed J Afzal, Shady A Amin. Molecular mechanisms of microbiome modulation by the eukaryotic secondary metabolite azelaic acid. eLife. 2024 Jan; 12(?):. doi: 10.7554/elife.88525. [PMID: 38189382]
  • Agata Markiewicz-Tomczyk, Elżbieta Budzisz, Anna Erkiert-Polguj. Clinical evaluation of anti-aging effects of combined therapy-Azelaic acid, phytic acid, and vitamin C applied layer by layer in females with Fitzpatrick skin types II and III. Journal of cosmetic dermatology. 2022 Dec; 21(12):6830-6839. doi: 10.1111/jocd.15359. [PMID: 36056802]
  • Attila L Ádám, György Kátay, András Künstler, Lóránt Király. Detection of Lipid Peroxidation-Derived Free Azelaic Acid, a Biotic Stress Marker and Other Dicarboxylic Acids in Tobacco by Reversed-Phase HPLC-MS Under Non-derivatized Conditions. Methods in molecular biology (Clifton, N.J.). 2022; 2526(?):191-200. doi: 10.1007/978-1-0716-2469-2_14. [PMID: 35657521]
  • 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]
  • Hang Gao, Miaojie Guo, Jianbo Song, Yeye Ma, Ziqin Xu. Signals in systemic acquired resistance of plants against microbial pathogens. Molecular biology reports. 2021 Apr; 48(4):3747-3759. doi: 10.1007/s11033-021-06344-7. [PMID: 33893927]
  • Supriya Kumari Singh, Saumya Chaubey, Anil Bansal, Gurpreet Kaur, Deepinder Singh Malik. Cosmeceutical Aptitudes of Azelaic Acid. Current drug research reviews. 2021; 13(3):222-229. doi: 10.2174/2589977513666210526122909. [PMID: 34042044]
  • Chunyan Wu, Mi-Young Jeong, Jung Yeon Kim, Giljae Lee, Ji-Sun Kim, Yu Eun Cheong, Hyena Kang, Chung Hwan Cho, Jimin Kim, Min Kyung Park, You Kyoung Shin, Kyoung Heon Kim, Geun Hee Seol, Seung Hoi Koo, GwangPyo Ko, Sung-Joon Lee. Activation of ectopic olfactory receptor 544 induces GLP-1 secretion and regulates gut inflammation. Gut microbes. 2021 Jan; 13(1):1987782. doi: 10.1080/19490976.2021.1987782. [PMID: 34674602]
  • Juan Bai, Renalison Farias-Pereira, Miran Jang, Yuan Zhang, Sang Mi Lee, Young-Suk Kim, Yeonhwa Park, Jun Bae Ahn, Gun-Hee Kim, Kee-Hong Kim. Azelaic Acid Promotes Caenorhabditis elegans Longevity at Low Temperature Via an Increase in Fatty Acid Desaturation. Pharmaceutical research. 2021 Jan; 38(1):15-26. doi: 10.1007/s11095-020-02975-w. [PMID: 33449249]
  • Nabeelah Bibi Sadeer, Kouadio Ibrahime Sinan, Zoltán Cziáky, József Jekő, Gokhan Zengin, Rajesh Jeewon, Hassan H Abdallah, Kannan R R Rengasamy, Mohamad Fawzi Mahomoodally. Assessment of the Pharmacological Properties and Phytochemical Profile of Bruguiera gymnorhiza (L.) Lam Using in Vitro Studies, in Silico Docking, and Multivariate Analysis. Biomolecules. 2020 05; 10(5):. doi: 10.3390/biom10050731. [PMID: 32392806]
  • Robert T Streeper, Christopher Louden, Elzbieta Izbicka. Oral Azelaic Acid Ester Decreases Markers of Insulin Resistance in Overweight Human Male Subjects. In vivo (Athens, Greece). 2020 May; 34(3):1173-1186. doi: 10.21873/invivo.11890. [PMID: 32354907]
  • Gabriele Micheletti, Natalia Calonghi, Giovanna Farruggia, Elena Strocchi, Vincenzo Palmacci, Dario Telese, Silvia Bordoni, Giulia Frisco, Carla Boga. Synthesis of Novel Structural Hybrids between Aza-Heterocycles and Azelaic Acid Moiety with a Specific Activity on Osteosarcoma Cells. Molecules (Basel, Switzerland). 2020 Jan; 25(2):. doi: 10.3390/molecules25020404. [PMID: 31963693]
  • Cristina Bez, Sree Gowrinadh Javvadi, Iris Bertani, Giulia Devescovi, Corrado Guarnaccia, David J Studholme, Alexander M Geller, Asaf Levy, Vittorio Venturi. AzeR, a transcriptional regulator that responds to azelaic acid in Pseudomonas nitroreducens. Microbiology (Reading, England). 2020 01; 166(1):73-84. doi: 10.1099/mic.0.000865. [PMID: 31621557]
  • 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]
  • Eduardo J S Brás, Ana Margarida Fortes, Virginia Chu, Pedro Fernandes, João Pedro Conde. Microfluidic device for the point of need detection of a pathogen infection biomarker in grapes. The Analyst. 2019 Aug; 144(16):4871-4879. doi: 10.1039/c9an01002e. [PMID: 31298663]
  • Michael Maes, Buranee Kanchanatawan, Sunee Sirivichayakul, André F Carvalho. In Schizophrenia, Increased Plasma IgM/IgA Responses to Gut Commensal Bacteria Are Associated with Negative Symptoms, Neurocognitive Impairments, and the Deficit Phenotype. Neurotoxicity research. 2019 Apr; 35(3):684-698. doi: 10.1007/s12640-018-9987-y. [PMID: 30552634]
  • Francesca Nicolì, Carmine Negro, Eliana Nutricati, Marzia Vergine, Alessio Aprile, Erika Sabella, Gina Damiano, Luigi De Bellis, Andrea Luvisi. Accumulation of Azelaic Acid in Xylella fastidiosa-Infected Olive Trees: A Mobile Metabolite for Health Screening. Phytopathology. 2019 Feb; 109(2):318-325. doi: 10.1094/phyto-07-18-0236-fi. [PMID: 30566025]
  • Nicolás M Cecchini, Suruchi Roychoudhry, DeQuantarius J Speed, Kevin Steffes, Arjun Tambe, Kristin Zodrow, Katerina Konstantinoff, Ho Won Jung, Nancy L Engle, Timothy J Tschaplinski, Jean T Greenberg. Underground Azelaic Acid-Conferred Resistance to Pseudomonas syringae in Arabidopsis. Molecular plant-microbe interactions : MPMI. 2019 01; 32(1):86-94. doi: 10.1094/mpmi-07-18-0185-r. [PMID: 30156481]
  • Sree Gowrinadh Javvadi, Paola Cescutti, Roberto Rizzo, Valentina Lonzarich, Luciano Navarini, Danilo Licastro, Corrado Guarnaccia, Vittorio Venturi. The spent culture supernatant of Pseudomonas syringae contains azelaic acid. BMC microbiology. 2018 11; 18(1):199. doi: 10.1186/s12866-018-1352-z. [PMID: 30486794]
  • Jian-Jun Chen, Shun-Jie Bai, Wen-Wen Li, Chan-Juan Zhou, Peng Zheng, Liang Fang, Hai-Yang Wang, Yi-Yun Liu, Peng Xie. Urinary biomarker panel for diagnosing patients with depression and anxiety disorders. Translational psychiatry. 2018 09; 8(1):192. doi: 10.1038/s41398-018-0245-0. [PMID: 30232320]
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  • A M Egorova, I A Tarchevsky. Azelaic Acid-Induced Enzymes of Phenolic Defense in Pea Roots. Doklady. Biochemistry and biophysics. 2018 Sep; 482(1):252-254. doi: 10.1134/s160767291805006x. [PMID: 30397886]
  • Aladdin Riad, Chandrakala Aluganti Narasimhulu, Pragney Deme, Sampath Parthasarathy. A Novel Mechanism for Atherosclerotic Calcification: Potential Resolution of the Oxidation Paradox. Antioxidants & redox signaling. 2018 08; 29(5):471-483. doi: 10.1089/ars.2017.7362. [PMID: 29237273]
  • Nadia Bouain, Santosh B Satbhai, Arthur Korte, Chorpet Saenchai, Guilhem Desbrosses, Pierre Berthomieu, Wolfgang Busch, Hatem Rouached. Natural allelic variation of the AZI1 gene controls root growth under zinc-limiting condition. PLoS genetics. 2018 04; 14(4):e1007304. doi: 10.1371/journal.pgen.1007304. [PMID: 29608565]
  • Eun-Ji Seo, Young Joo Yeon, Joo-Hyun Seo, Jung-Hoo Lee, Jhoanne P Boñgol, Yuri Oh, Jong Moon Park, Sang-Min Lim, Choul-Gyun Lee, Jin-Byung Park. Enzyme/whole-cell biotransformation of plant oils, yeast derived oils, and microalgae fatty acid methyl esters into n-nonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid. Bioresource technology. 2018 Mar; 251(?):288-294. doi: 10.1016/j.biortech.2017.12.036. [PMID: 29288957]
  • Arnaud T Djami-Tchatchou, Efficient N Ncube, Paul A Steenkamp, Ian A Dubery. Similar, but different: structurally related azelaic acid and hexanoic acid trigger differential metabolomic and transcriptomic responses in tobacco cells. BMC plant biology. 2017 Nov; 17(1):227. doi: 10.1186/s12870-017-1157-5. [PMID: 29187153]
  • Takaomi Yaguchi, Tomohisa Kinami, Tetsuya Ishida, Takaomi Yasuhara, Kosaku Takahashi, Hideyuki Matsuura. Induction of plant disease resistance upon treatment with yeast cell wall extract. Bioscience, biotechnology, and biochemistry. 2017 Nov; 81(11):2071-2078. doi: 10.1080/09168451.2017.1379351. [PMID: 28950768]
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  • M I Mhlongo, F Tugizimana, L A Piater, P A Steenkamp, N E Madala, I A Dubery. Untargeted metabolomics analysis reveals dynamic changes in azelaic acid- and salicylic acid derivatives in LPS-treated Nicotiana tabacum cells. Biochemical and biophysical research communications. 2017 Jan; 482(4):1498-1503. doi: 10.1016/j.bbrc.2016.12.063. [PMID: 27956183]
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  • Shanmugam Muthulakshmi, Alok K Chakrabarti, Sanjay Mukherjee. Gene expression profile of high-fat diet-fed C57BL/6J mice: in search of potential role of azelaic acid. Journal of physiology and biochemistry. 2015 Mar; 71(1):29-42. doi: 10.1007/s13105-014-0376-6. [PMID: 25575741]
  • John W Gordy, B Rogers Leonard, David Blouin, Jeffrey A Davis, Michael J Stout. Comparative Effectiveness of Potential Elicitors of Plant Resistance against Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae) in Four Crop Plants. PloS one. 2015; 10(9):e0136689. doi: 10.1371/journal.pone.0136689. [PMID: 26332833]
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