MANDELIC ACID (BioDeep_00000265246)

Main id: BioDeep_00000014372

 

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


L-(+)-Mandelic acid

化学式: C8H8O3 (152.0473418)
中文名称: DL-扁桃酸, (R)-(-)-扁桃酸, 扁桃酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC=C(C=C1)C(C(=O)O)O
InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)

描述信息

B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions > B05CA - Antiinfectives
A 2-hydroxy monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are substituted by phenyl and hydroxyl groups.
D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use
C254 - Anti-Infective Agent > C255 - Urinary Anti-Infective Agent
D-(-)-Mandelic acid is a natural compound isolated from bitter almonds.
D-(-)-Mandelic acid is a natural compound isolated from bitter almonds.
Mandelic acid ((±)-Mandelic acid), an alpha-hydroxycarboxylic acid, has been widely used as an intermediate of pharmaceutical and fine chemicals. Mandelic acid shows antimicrobial activity and has been used for the research of urinary tract infections and vaginal trichomoniasis. Mandelic acid exhibits high sperm-immobilizing activity and low vaginal irritation[1][2].

同义名列表

6 个代谢物同义名

L-(+)-Mandelic acid; DL-Mandelic acid; MANDELIC ACID; D-(-)-MANDELIC ACID; (r)-Mandelic acid; (±)-Mandelic acid



数据库引用编号

34 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)

15 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

  • Yu-Qing Zhang, Xin Wang, Huabin Shi, Faisal Siddique, Jiaxin Xian, Aiting Song, Boli Wang, Zhibing Wu, Zi-Ning Cui. Design and Synthesis of Mandelic Acid Derivatives for Suppression of Virulence via T3SS against Citrus Canker. Journal of agricultural and food chemistry. 2024 May; 72(17):9611-9620. doi: 10.1021/acs.jafc.3c07681. [PMID: 38646906]
  • Wen-Yu Chen, Yan-Peng Fu, Hui Tu, Wen Zhong, Liang Zhou. The association between exposure to volatile organic compounds and serum lipids in the US adult population. Lipids in health and disease. 2023 Aug; 22(1):129. doi: 10.1186/s12944-023-01895-z. [PMID: 37568143]
  • Shuaitao Hou, Huabin Shi, Hong Zhang, Zhibing Wu, Deyu Hu. Synthesis, Antifungal Evaluation, 3D-QSAR, and Preliminarily Mechanism Study of Novel Chiral Mandelic Acid Derivatives. Journal of agricultural and food chemistry. 2023 May; 71(20):7631-7641. doi: 10.1021/acs.jafc.2c09006. [PMID: 37179490]
  • Biao Chen, Dandan Song, Huabin Shi, Kuai Chen, Zhibing Wu, Huifang Chai. Design, Synthesis, In Vitro Antifungal Activity and Mechanism Study of the Novel 4-Substituted Mandelic Acid Derivatives. International journal of molecular sciences. 2023 May; 24(10):. doi: 10.3390/ijms24108898. [PMID: 37240243]
  • Banrida Wahlang, Tyler C Gripshover, Hong Gao, Tatiana Krivokhizhina, Rachel J Keith, Israel D Sithu, Shesh N Rai, Aruni Bhatnagar, Craig J McClain, Sanjay Srivastava, Mathew C Cave. Associations Between Residential Exposure to Volatile Organic Compounds and Liver Injury Markers. Toxicological sciences : an official journal of the Society of Toxicology. 2021 12; 185(1):50-63. doi: 10.1093/toxsci/kfab119. [PMID: 34668566]
  • Shanila Akhter, Hafiz Muhammad Irfan, - Alamgeer, Shafeeq Ur Rahman, Mukhtar Ansari, Zaid Mustafa, Muhammad Bilal Latif. Toxicity studies and anti-arthritic effect of mandelic acid (2-hydroxy -2-phenyl acetic acid) using in vitro and in vivo techniques. Pakistan journal of pharmaceutical sciences. 2021 Nov; 34(6(Supplementary)):2281-2287. doi: NULL. [PMID: 35039264]
  • 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]
  • Minjie Xia, Mingjun Yang, Yuzhu Wang, Fang Tian, Jingying Hu, Wei Yang, Shimin Tao, Lu Lu, Xuncheng Ding, Shibo Jiang, Weihua Li. dl-Mandelic acid exhibits high sperm-immobilizing activity and low vaginal irritation: A potential non-surfactant spermicide for contraception. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Jun; 126(?):110104. doi: 10.1016/j.biopha.2020.110104. [PMID: 32224371]
  • 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]
  • Razzagh Rahimpoor, Abdulrahman Bahrami, Davood Nematollahi, Farshid Ghorbani Shahna, Maryam Farhadian. Facile and sensitive determination of urinary mandelic acid by combination of metal organic frameworks with microextraction by packed sorbents. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 May; 1114-1115(?):45-54. doi: 10.1016/j.jchromb.2019.03.023. [PMID: 30927741]
  • Mahmoud Mohamadyan, Mahmood Moosazadeh, Absalte Borji, Narges Khanjani, Somayeh Rahimi Moghadam. Occupational exposure to styrene and its relation with urine mandelic acid, in plastic injection workers. Environmental monitoring and assessment. 2019 Jan; 191(2):62. doi: 10.1007/s10661-019-7191-z. [PMID: 30635735]
  • Renaud Persoons, Justine Richard, Claire Herve, Sarah Montlevier, Marie Marques, Anne Maitre. Biomonitoring of styrene occupational exposures: Biomarkers and determinants. Toxicology letters. 2018 Dec; 298(?):99-105. doi: 10.1016/j.toxlet.2018.06.1211. [PMID: 29940302]
  • Muhammad Zahoor, Sadaf Shafiq, Habib Ullah, Abdul Sadiq, Farhat Ullah. Isolation of quercetin and mandelic acid from Aesculus indica fruit and their biological activities. BMC biochemistry. 2018 06; 19(1):5. doi: 10.1186/s12858-018-0095-7. [PMID: 29940844]
  • Abdulrahman Bahrami, Farhad Ghamari, Yadollah Yamini, Farshid Ghorbani Shahna, Ali Koolivand. Ion-pair-based hollow-fiber liquid-phase microextraction combined with high-performance liquid chromatography for the simultaneous determination of urinary benzene, toluene, and styrene metabolites. Journal of separation science. 2018 Jan; 41(2):501-508. doi: 10.1002/jssc.201700685. [PMID: 29082608]
  • Esmaeel Soleimani, Abdulrahman Bahrami, Abbas Afkhami, Farshid Ghorbani Shahna. Selective determination of mandelic acid in urine using molecularly imprinted polymer in microextraction by packed sorbent. Archives of toxicology. 2018 Jan; 92(1):213-222. doi: 10.1007/s00204-017-2057-z. [PMID: 28871328]
  • Luciano Vitali, Samantha Gonçalves, Victor Rodrigues, Valfredo T Fávere, Gustavo A Micke. Development of a fast method for simultaneous determination of hippuric acid, mandelic acid, and creatinine in urine by capillary zone electrophoresis using polymer multilayer-coated capillary. Analytical and bioanalytical chemistry. 2017 Mar; 409(7):1943-1950. doi: 10.1007/s00216-016-0142-4. [PMID: 27988799]
  • Jialiang Guo, Yuan Xiao, Yuanjing Lin, Qiaoxuan Zhang, Yiqun Chang, Jacques Crommen, Zhengjin Jiang. Influence of the linking spacer length and type on the enantioseparation ability of β-cyclodextrin functionalized monoliths. Talanta. 2016 May; 152(?):259-68. doi: 10.1016/j.talanta.2016.02.016. [PMID: 26992519]
  • Axelle Marchand, Rocio Aranda-Rodriguez, Robert Tardif, Andy Nong, Sami Haddad. Evaluation and modeling of the impact of coexposures to VOC mixtures on urinary biomarkers. Inhalation toxicology. 2016; 28(6):260-73. doi: 10.3109/08958378.2016.1162232. [PMID: 27053005]
  • Guojian Shao, Juan Yu, Danqing Wu. [Determination of mandelic acid and phenylglyoxylic acid in urine by reagent-free ion chromatography]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2015 Apr; 33(4):301-3. doi: . [PMID: 26506786]
  • Damiano Carbonari, Antonella Mansi, Anna Rita Proietto, Enrico Paci, Rossana Claudia Bonanni, Monica Gherardi, Maria Pia Gatto, Renata Sisto, Giovanna Tranfo. Influence of genetic polymorphisms of styrene-metabolizing enzymes on the levels of urinary biomarkers of styrene exposure. Toxicology letters. 2015 Mar; 233(2):156-62. doi: 10.1016/j.toxlet.2015.01.002. [PMID: 25562543]
  • Olga Sosedov, Andreas Stolz. Improvement of the amides forming capacity of the arylacetonitrilase from Pseudomonas fluorescens EBC191 by site-directed mutagenesis. Applied microbiology and biotechnology. 2015 Mar; 99(6):2623-35. doi: 10.1007/s00253-014-6061-4. [PMID: 25248440]
  • Cheng Xu, Qian Liu, Hui Liu, Paul Héroux, Qunwei Zhang, Zhao-Yan Jiang, Aihua Gu. Low Serum Testosterone Levels Are Associated with Elevated Urinary Mandelic Acid, and Strontium Levels in Adult Men According to the US 2011-2012 National Health and Nutrition Examination Survey. PloS one. 2015; 10(5):e0127451. doi: 10.1371/journal.pone.0127451. [PMID: 25996772]
  • Bixia Yao, Xinmei Yang, Lizhen Guo, Shanshan Kang, Wen Weng. Development of a composite chiral stationary phase from BSA and β-cyclodextrin-bonded silica. Journal of chromatographic science. 2014 Nov; 52(10):1233-8. doi: 10.1093/chromsci/bmt203. [PMID: 24448668]
  • Sawsan Farouk Helal, Wessam Sabry Elshafy. Health hazards among workers in plastic industry. Toxicology and industrial health. 2013 Oct; 29(9):812-9. doi: 10.1177/0748233712442728. [PMID: 22609858]
  • Qiu-Yun Wang, Ya-Jin Xiong, Bao-Zhu Lu, Jun Fan, Sheng-Run Zheng, Wei-Guang Zhang. Effect of chromatographic conditions on enantioseparation of bovine serum albumin chiral stationary phase in HPLC and thermodynamic studies. Chirality. 2013 Sep; 25(9):487-92. doi: 10.1002/chir.22163. [PMID: 23913549]
  • Fang Zhang, Jin-long Meng, Hua Shao, Zhi-hu Zhang, Bin Feng. [Influence of genetic polymorphisms of epoxide hydrolase 1 on metabolism of styrene in body]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2013 Jul; 31(7):496-9. doi: . [PMID: 24053912]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, James A Pfister, Kip E Panter. Fetal muscle-type nicotinic acetylcholine receptor activation in TE-671 cells and inhibition of fetal movement in a day 40 pregnant goat model by optical isomers of the piperidine alkaloid coniine. The Journal of pharmacology and experimental therapeutics. 2013 Jan; 344(1):295-307. doi: 10.1124/jpet.112.199588. [PMID: 23086230]
  • Igor Linhart, Jaroslav Mráz, Ludmila Dabrowská, Milan Mališ, Jan Krouželka, Marek Kořínek. Vinylphenylmercapturic acids in human urine as biomarkers of styrene ring oxidation. Toxicology letters. 2012 Sep; 213(2):260-5. doi: 10.1016/j.toxlet.2012.06.012. [PMID: 22750350]
  • Mária Poláková, Zdenka Krajcovicová, Vladimír Melus, Mária Stefkovicová, Margaréta Sulcová. Study of urinary concentrations of mandelic acid in employees exposed to styrene. Central European journal of public health. 2012 Sep; 20(3):226-32. doi: 10.21101/cejph.a3649. [PMID: 23285526]
  • Giovanna Tranfo, Monica Gherardi, E Paci, Mariapia Gatto, A Gordiani, Lidia Caporossi, Silvia Capanna, Renata Sisto, B Papaleo, Carla Fiumalbi, Patrizia Garofani. Occupational exposure to styrene in the fibreglass reinforced plastic industry: comparison between two different manufacturing processes. La Medicina del lavoro. 2012 Sep; 103(5):402-12. doi: NULL. [PMID: 23077800]
  • Mina Ha, Hojang Kwon, Hae-Kwan Cheong, Sinye Lim, Seung Jin Yoo, Eun-Jung Kim, Seok Gun Park, Jeongae Lee, Bong Chul Chung. Urinary metabolites before and after cleanup and subjective symptoms in volunteer participants in cleanup of the Hebei Spirit oil spill. The Science of the total environment. 2012 Jul; 429(?):167-73. doi: 10.1016/j.scitotenv.2012.04.036. [PMID: 22591993]
  • Frédéric Cosnier, Hervé Nunge, Benoît Cossec, Laurent Gaté. Simultaneous determination of aromatic acid metabolites of styrene and styrene-oxide in rat urine by gas chromatography-flame ionization detection. Journal of analytical toxicology. 2012 Jun; 36(5):312-8. doi: 10.1093/jat/bks015. [PMID: 22492963]
  • Sébastien Gagné. A reliable method by ultra-performance liquid chromatography coupled with tandem mass spectrometry to quantify and confirm simultaneously the presence of solvent metabolites in workers' urine. Rapid communications in mass spectrometry : RCM. 2012 Apr; 26(7):845-52. doi: 10.1002/rcm.6163. [PMID: 22368065]
  • Carla Costa, Solange Costa, Susana Silva, Patrícia Coelho, Mónica Botelho, Jorge Gaspar, José Rueff, Blanca Laffon, João Paulo Teixeira. DNA damage and susceptibility assessment in industrial workers exposed to styrene. Journal of toxicology and environmental health. Part A. 2012; 75(13-15):735-46. doi: 10.1080/15287394.2012.688488. [PMID: 22788361]
  • Zhoutong Sun, Yuanyuan Ning, Lixia Liu, Yingmiao Liu, Bingbing Sun, Weihong Jiang, Chen Yang, Sheng Yang. Metabolic engineering of the L-phenylalanine pathway in Escherichia coli for the production of S- or R-mandelic acid. Microbial cell factories. 2011 Sep; 10(?):71. doi: 10.1186/1475-2859-10-71. [PMID: 21910908]
  • Mi-Young Lee, Jeong Sun Yang, Seong-Kyu Kang. External quality assessment scheme for biological monitoring of occupational exposure to toxic chemicals. Safety and health at work. 2011 Sep; 2(3):229-35. doi: 10.5491/shaw.2011.2.3.229. [PMID: 22953206]
  • Marianna A Patrauchan, J Jacob Parnell, Michael P McLeod, Christine Florizone, James M Tiedje, Lindsay D Eltis. Genomic analysis of the phenylacetyl-CoA pathway in Burkholderia xenovorans LB400. Archives of microbiology. 2011 Sep; 193(9):641-50. doi: 10.1007/s00203-011-0705-x. [PMID: 21519854]
  • Liang Jin, Pei-ying Hao, Sheng-zhang Dong, Ya-lin Bian, Xiao-ping Yu. Antifeedant and insecticidal effects of mandelic acid on the brown planthopper Nilaparvata lugens Stål. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2011 Sep; 66(9-10):499-506. doi: 10.1515/znc-2011-9-1010. [PMID: 22191216]
  • Manisone Khennavong, Viengmon Davone, Manivanh Vongsouvath, Rattanaphone Phetsouvanh, Joy Silisouk, Olay Rattana, Mayfong Mayxay, Josée Castonguay-Vanier, Catrin E Moore, Michel Strobel, Paul N Newton. Urine antibiotic activity in patients presenting to hospitals in Laos: implications for worsening antibiotic resistance. The American journal of tropical medicine and hygiene. 2011 Aug; 85(2):295-302. doi: 10.4269/ajtmh.2011.11-0076. [PMID: 21813851]
  • Fu-Kuei Chang, I-Fang Mao, Mei-Lien Chen, Shu-Fang Cheng. Urinary 8-hydroxydeoxyguanosine as a biomarker of oxidative DNA damage in workers exposed to ethylbenzene. The Annals of occupational hygiene. 2011 Jun; 55(5):519-25. doi: 10.1093/annhyg/mer010. [PMID: 21430133]
  • Sirilak Wongvijitsuk, Panida Navasumrit, Udomratana Vattanasit, Varabhorn Parnlob, Mathuros Ruchirawat. Low level occupational exposure to styrene: its effects on DNA damage and DNA repair. International journal of hygiene and environmental health. 2011 Mar; 214(2):127-37. doi: 10.1016/j.ijheh.2010.09.007. [PMID: 21030303]
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  • Florent Lassalle, Tony Campillo, Ludovic Vial, Jessica Baude, Denis Costechareyre, David Chapulliot, Malek Shams, Danis Abrouk, Céline Lavire, Christine Oger-Desfeux, Florence Hommais, Laurent Guéguen, Vincent Daubin, Daniel Muller, Xavier Nesme. Genomic species are ecological species as revealed by comparative genomics in Agrobacterium tumefaciens. Genome biology and evolution. 2011; 3(?):762-81. doi: 10.1093/gbe/evr070. [PMID: 21795751]
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  • Yan-Rang Wang, De-Yi Yang, Ming Zhang, Qian Wang, Jing Liu, Jian-Guo Li, Xue-Ying Yang. [Influence of ethylbenzene on the levels of mandelic acid and phenylglyoxylic acid in urine, ultrastructure and the expressions of Mitochondrial apoptotic-related proteins in the rat nephridial tissues]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2009 Nov; 27(11):655-9. doi: . [PMID: 20137408]
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