2-Methylhippuric acid (BioDeep_00000017759)
Secondary id: BioDeep_00000415948
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
Metabolite Card
Formula: C10H11NO3 (193.0738896)
Chinese Names: 2-甲基马尿酸
Spectrum Hits:
Top Source Homo sapiens(blood) 2.44%
Molecular Structure
SMILES: CC1=C(C=CC=C1)C(=O)NCC(O)=O
InChI: InChI=1S/C10H11NO3/c1-7-4-2-3-5-8(7)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)
Description
2-Methylhippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases, the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine <--> CoA + N-acylglycine. 2-Methylhippuric acid is a metabolite of xylene which is an aromatic hydrocarbon widely used as a solvant. Its level can be measured in the urine of workers exposed to xylene (PMID:8689499). 2-Methylhippuric acid is an endogenous phenolic acid metabolite detected after the consumption of whole grain.
Methylhippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:
2-(2-Methylbenzamido)acetic acid is a metabolite detected in urine.
Synonyms
19 synonym names
2-[(2-methylphenyl)formamido]acetic acid; 2-(2-Methylbenzamido)acetic acid; N-(2-Methylbenzoyl)-glycine; N-(2-Methylbenzoyl)glycine; Ortho-methylhippuric acid; N-(Methylbenzoyl)-glycine; N-(Methylbenzoyl)glycine; 2-Methylhippuric acid; O-Methylhippuric acid; N-(O-Toluoyl)-glycine; N-(O-Toluoyl)glycine; O-Methylhippic acid; 2-Methylhippic acid; METHYL HIPPURATE; 2-Methylhippate; O-Methylhippate; O-Toluric acid; O-Tolic acid; O-Tolate
Cross Reference
11 cross reference id
- ChEBI: CHEBI:68455
- PubChem: 91637
- HMDB: HMDB0011723
- ChEMBL: CHEMBL457228
- Wikipedia: Methylhippuric acid
- foodb: FDB028406
- chemspider: 82742
- CAS: 42013-20-7
- PMhub: MS000000147
- RefMet: 2-Methylhippuric acid
- medchemexpress: HY-W015060
Classification Terms
Related Pathways
Reactome(0)
BioCyc(0)
PlantCyc(0)
Biological Process
0 related biological process reactions.
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
3 organism taxonomy source information
- 9606 Homo sapiens: 10.1007/S11306-016-1051-4
- 9606 Homo sapiens: 10.1007/S11306-016-1051-4
- 9606 Homo sapiens: -
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。
Literature Reference
- Chun-Hui Chiu, Chi-Tsung Chen, Ming-Huei Cheng, Li-Heng Pao, Chi Wang, Gwo-Hwa Wan. Use of urinary hippuric acid and o-/p-/m-methyl hippuric acid to evaluate surgical smoke exposure in operating room healthcare personnel.
Ecotoxicology and environmental safety.
2021 Jul; 217(?):112231. doi:
10.1016/j.ecoenv.2021.112231
. [PMID: 33862429] - Víctor R De Jesús, Daniel F Milan, Young M Yoo, Luyu Zhang, Wanzhe Zhu, Deepak Bhandari, Kevin S Murnane, Benjamin C Blount. Examination of xylene exposure in the U.S. Population through biomonitoring: NHANES 2005-2006, 2011-2016.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2021 Feb; 26(1):65-73. doi:
10.1080/1354750x.2020.1861100
. [PMID: 33284648] - Xiao-Dong Sun, Hai-Long Wu, Zhi Liu, Yue Chen, Jun-Chen Chen, Li Cheng, Yu-Jie Ding, Ru-Qin Yu. Target-based metabolomics for fast and sensitive quantification of eight small molecules in human urine using HPLC-DAD and chemometrics tools resolving of highly overlapping peaks.
Talanta.
2019 Aug; 201(?):174-184. doi:
10.1016/j.talanta.2019.03.090
. [PMID: 31122409] - Daniela Remane, Soeren Grunwald, Henrike Hoeke, Andrea Mueller, Stefan Roeder, Martin von Bergen, Dirk K Wissenbach. Validation of a multi-analyte HPLC-DAD method for determination of uric acid, creatinine, homovanillic acid, niacinamide, hippuric acid, indole-3-acetic acid and 2-methylhippuric acid in human urine.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2015 Aug; 998-999(?):40-4. doi:
10.1016/j.jchromb.2015.06.021
. [PMID: 26151191] - Henricus A M Mutsaers, Lambertus P van den Heuvel, Lauke H J Ringens, Anita C A Dankers, Frans G M Russel, Jack F M Wetzels, Joost G Hoenderop, Rosalinde Masereeuw. Uremic toxins inhibit transport by breast cancer resistance protein and multidrug resistance protein 4 at clinically relevant concentrations.
PloS one.
2011 Apr; 6(4):e18438. doi:
10.1371/journal.pone.0018438
. [PMID: 21483698] - Zuzana Valnickova, Morten Thaysen-Andersen, Peter Højrup, Trine Christensen, Kristian W Sanggaard, Torsten Kristensen, Jan J Enghild. Biochemical characterization of bovine plasma thrombin-activatable fibrinolysis inhibitor (TAFI).
BMC biochemistry.
2009 May; 10(?):13. doi:
10.1186/1471-2091-10-13
. [PMID: 19416536] - Richard S Lord, J Alexander Bralley. Clinical applications of urinary organic acids. Part I: Detoxification markers.
Alternative medicine review : a journal of clinical therapeutic.
2008 Sep; 13(3):205-15. doi:
NULL
. [PMID: 18950247] - Carlos Humberto Torres, Marcela E Varona, Angélica Lancheros, Rosa Isabel Patiño, Helena Groot. [DNA damage assessment and biological monitoring of occupational exposure to organic solvents, 2006].
Biomedica : revista del Instituto Nacional de Salud.
2008 Mar; 28(1):126-38. doi:
. [PMID: 18645668]
- Michael Jason Bishop, Brian S Crow, Kasey D Kovalcik, Joe George, James A Bralley. Quantification of urinary zwitterionic organic acids using weak-anion exchange chromatography with tandem MS detection.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2007 Apr; 848(2):303-10. doi:
10.1016/j.jchromb.2006.10.042
. [PMID: 17118722] - H Moriwaki, Y Tsujimoto, M Shimizu, T Noda, M Warashina, M Tanaka. Influence of sodium benzoate on the metabolism of o-xylene in the rat.
Xenobiotica; the fate of foreign compounds in biological systems.
2005 May; 35(5):487-97. doi:
10.1080/00498250500057476
. [PMID: 16012080] - P Kongtip, J Vararussami, V Pruktharathikul. Modified method for determination of hippuric acid and methylhippuric acid in urine by gas chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
2001 Feb; 751(1):199-203. doi:
10.1016/s0378-4347(00)00463-1
. [PMID: 11232852] - C Burrini. [The simultaneous determination of hippuric acid, o-, m-, p-methylhippuric acids, mandelic acid and phenylglyoxylic acid in urine by HPLC].
La Medicina del lavoro.
1998 Sep; 89(5):404-11. doi:
. [PMID: 10064945]
- K J Lee, J J Lee, D C Moon. Application of micellar electrokinetic capillary chromatography for monitoring of hippuric and methylhippuric acid in human urine.
Electrophoresis.
1994 Jan; 15(1):98-102. doi:
10.1002/elps.1150150115
. [PMID: 8143687] - O Inoue, K Seiji, T Kawai, T Watanabe, C Jin, S X Cai, Z Chen, Q S Qu, T Zhang, M Ikeda. Excretion of methylhippuric acids in urine of workers exposed to a xylene mixture: comparison among three xylene isomers and toluene.
International archives of occupational and environmental health.
1993; 64(7):533-9. doi:
10.1007/bf00381104
. [PMID: 8482596] - O Inoue, K Seiji, T Suzuki, T Watanabe, H Nakatsuka, H Satoh, M Ikeda. Simultaneous determination of hippuric acid, o-, m-, and p-methylhippuric acid, phenylglyoxylic acid, and mandelic acid by HPLC.
Bulletin of environmental contamination and toxicology.
1991 Aug; 47(2):204-10. doi:
10.1007/bf01688641
. [PMID: 1912696] - H Matsui, T Sekiya. High-performance liquid chromatographic separation of urinary hippuric and o-, m- and p-methylhippuric acids with a beta-cyclodextrin-bonded column.
Journal of chromatography.
1989 Nov; 496(1):189-93. doi:
10.1016/s0378-4347(00)82565-7
. [PMID: 2592511] - R Tardif, J Brodeur, G L Plaa. Simultaneous high-performance liquid chromatographic analysis of hippuric acid and ortho-, meta-, and para-methylhippuric acids in urine.
Journal of analytical toxicology.
1989 Nov; 13(6):313-6. doi:
10.1093/jat/13.6.313
. [PMID: 2607759] - M Buratti, G Caravelli, O Pellegrino, D Xaiz, C Valla, R Giampiccolo, A Colombi. [Determination of hippuric and methylhippuric acids with high pressure liquid chromatography: comparison between chromatographic and colorimetric methods].
La Medicina del lavoro.
1988 Nov; 79(6):489-99. doi:
NULL
. [PMID: 3246973] - M Ogata, T Taguchi. Simultaneous determination of urinary creatinine and metabolites of toluene, xylene, styrene, ethylbenzene and phenol by automated high performance liquid chromatography.
International archives of occupational and environmental health.
1988; 61(1-2):131-40. doi:
10.1007/bf00381617
. [PMID: 3198279] - K Engström, V Riihimäki. Determination of methylhippuric acids in urine by gas chromatography.
IARC scientific publications.
1988; ?(85):313-8. doi:
NULL
. [PMID: 3182055] - Y Takeuchi, T Sakai, Y Ikeya, T Araki, K Ushio, S Yanagihara. [Improved high performance liquid chromatography determination of hippuric acid and methylhippuric acid isomers in urine].
Sangyo igaku. Japanese journal of industrial health.
1986 Nov; 28(6):455-61. doi:
10.1539/joh1959.28.455
. [PMID: 3586389] - C Lacroix, F Inger, S Menager, O Lafont. [Simultaneous determination of urinary hippuric acid and o-, m-, p-methylhippuric acids with liquid chromatography].
Journal of chromatography.
1986 Oct; 382(?):275-9. doi:
NULL
. [PMID: 3782394] - I Lundberg, J Sollenberg. Correlation of xylene exposure and methyl hippuric acid excretion in urine among paint industry workers.
Scandinavian journal of work, environment & health.
1986 Apr; 12(2):149-53. doi:
10.5271/sjweh.2164
. [PMID: 3726497] - M Ogata, T Taguchi. [Quantitative determination of urinary hippuric acid and o-, m- and p-methyl hippuric acids by high performance liquid chromatography].
Sangyo igaku. Japanese journal of industrial health.
1986 Mar; 28(2):120-1. doi:
10.1539/joh1959.28.120
. [PMID: 3761712] - M Ogata, T Taguchi. Quantitative analysis of urinary glycine conjugates by high performance liquid chromatography: excretion of hippuric acid and methylhippuric acids in the urine of subjects exposed to vapours of toluene and xylenes.
International archives of occupational and environmental health.
1986; 58(2):121-9. doi:
10.1007/bf00380763
. [PMID: 3744566] - T Sakai, Y Niinuma, S Yanagihara, K Ushio. Simultaneous determination of hippuric acid and o-, m- and p-methylhippuric acids in urine by high-performance liquid chromatography.
Journal of chromatography.
1983 Aug; 276(1):182-8. doi:
10.1016/s0378-4347(00)85080-x
. [PMID: 6672011] - Y Niinuma, T Sakai, S Yanagihara, S Nakahira, Y Kunugi, K Ushio. Simultaneous determinations of urinary hippuric and methylhippuric acids in solvent-workers by high performance liquid chromatography.
Sangyo igaku. Japanese journal of industrial health.
1982 May; 24(3):322-3. doi:
10.1539/joh1959.24.322
. [PMID: 7143804] - M Ogata, Y Yamazaki, R Sugihara, Y Shimada, T Meguro. Quantitation of urinary o-xylene metabolites of rats and human beings by high performance liquid chromatography.
International archives of occupational and environmental health.
1980; 46(2):127-39. doi:
10.1007/bf00378191
. [PMID: 7399721] - W M O'Neill, W B Etheridge, H A Bloomer. High-dose corticosteroids: their use in treating idiopathic rapidly progressive glomerulonephritis.
Archives of internal medicine.
1979 May; 139(5):514-8. doi:
10.1001/archinte.139.5.514
. [PMID: 443944]