Mandelic acid (BioDeep_00000014372)

 

Secondary id: BioDeep_00000265246, BioDeep_00000400469, BioDeep_00000415754, BioDeep_00001868133

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


(S)-alpha-Hydroxybenzeneacetic acid

化学式: C8H8O3 (152.0473)
中文名称: 扁桃酸, (S)-(+)-扁桃酸, （S） -扁桃酸, DL-扁桃酸
谱图信息: 最多检出来源 Homo sapiens(plant) 14.78%

Reviewed

Last reviewed on 2024-07-29.

Cite this Page

Mandelic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/mandelic_acid (retrieved 2024-12-23) (BioDeep RN: BioDeep_00000014372). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(=O)([C@@H](O)c1ccccc1)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

It is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes. Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents. Mandelic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism.
It is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes.
B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions > B05CA - Antiinfectives
D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids
Acquisition and generation of the data is financially supported in part by CREST/JST.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use
C254 - Anti-Infective Agent > C255 - Urinary Anti-Infective Agent
KEIO_ID M057
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

61 个代谢物同义名

(S)-alpha-Hydroxybenzeneacetic acid; (2S)-2-hydroxy-2-phenylacetic acid; (S)-2-Hydroxy-2-phenylacetic acid; alpha-Hydroxybenzeneacetic acid; (S)-alpha-Hydroxybenzeneacetate; alpha-Hydroxy-alpha-toluic acid; 2-Hydroxy-2-phenylethanoic acid; (S)-a-Hydroxybenzeneacetic acid; (S)-Α-hydroxybenzeneacetic acid; alpha-Hydroxyphenylacetic acid; (S)-2-Hydroxy-2-phenylacetate; 2-Hydroxy-2-phenylacetic acid; DL-Hydroxy(phenyl)acetic acid; 2-Phenyl-2-hydroxyacetic acid; alpha-Hydroxy-alpha-toluate; alpha-Hydroxybenzeneacetate; a-Hydroxybenzeneacetic acid; 2-Hydroxy-2-phenylethanoate; (S)-Α-hydroxybenzeneacetate; (S)-a-Hydroxybenzeneacetate; a-Hydroxyphenylacetic acid; alpha-Hydroxyphenylacetate; 2-Hydroxy-2-phenylacetate; 2-Phenyl-2-hydroxyacetate; DL-Hydroxy(phenyl)acetate; Phenylhydroxyacetic acid; a-Hydroxybenzeneacetate; a-Hydroxy-a-toluic acid; a-Hydroxyphenylacetate; 2-Phenylglycolic acid; (S)-(+)-Mandelic acid; Phenylhydroxyacetate; Phenylglycolic acid; L-(+)-Mandelic acid; a-Hydroxy-a-toluate; (RS)-Mandelic acid; (S)-Mandelic acid; DL-Amygdalic acid; 2-Phenylglycolate; Paramandelic acid; (S)-Mandelsaeure; DL-Mandelic acid; L-Mandelic acid; Phenylglycolate; (RS)-Mandelate; Amygdalic acid; Paramandelate; DL-Amygdalate; MANDELIC ACID; (S)-Mandelate; DL-Mandelate; Almond acid; L-Mandelate; Amygdalate; Uromaline; Mandelate; Mandelic acid; (±)-Mandelic acid; (S)-Mandelate; Mandelic acid; (S)-Mandelic acid



数据库引用编号

36 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)

45 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


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]
  • 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]
  • 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]
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  • 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]
  • 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]
  • 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]
  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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