n-Methylhippuric acid (N-MHPA) is a urinary metabolite of toluene, a volatile organic compound found in various industrial products and environmental sources. It is formed in the liver through the conjugation of toluene with glycine. N-MHPA levels in urine are used as a biomarker of toluene exposure and are widely studied to assess occupational and environmental health risks. The synthesis of N-MHPA involves the reaction of toluene with glycine in the presence of enzymes such as glycine N-acyltransferase. Studies have shown that N-MHPA can have a variety of effects on the body, including neurotoxicity, hepatotoxicity, and reproductive toxicity. Its importance lies in its ability to serve as a reliable indicator of toluene exposure, allowing researchers and clinicians to monitor toluene-related health risks in various populations. This compound is extensively studied to understand the long-term health effects of toluene exposure, particularly in individuals working in industries that handle toluene or are exposed to toluene in the environment.'
N-methylhippuric acid : An N-acylglycine that is N-methylglycine in which the hydrogen of the amino group is substituted by a benzoyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 75728 |
| CHEMBL ID | 66391 |
| CHEBI ID | 141362 |
| SCHEMBL ID | 2282162 |
| MeSH ID | M0064542 |
| Synonym |
|---|
| EN300-30808 |
| BB 0259304 |
| glycine, n-benzoyl-n-methyl- |
| n-methylhippuric acid |
| nsc-122438 |
| benzoylsarcosine |
| nsc122438 |
| n-benzoylsarcosine |
| n-benzoyl-n-methylglycine |
| 2568-34-5 |
| hippuric acid, .beta.-methyl- |
| sarcosine, n-benzoyl- |
| CHEMBL66391 , |
| smr001295234 |
| MLS002206418 |
| 2-[benzoyl(methyl)amino]acetic acid |
| FT-0695166 |
| bdbm50009998 |
| (benzoyl-methyl-amino)-acetic acid |
| 2-(n-methyl-1-phenylformamido)acetic acid |
| [benzoyl(methyl)amino]acetic acid |
| CHEBI:141362 |
| [n-benzoyl-n-methylamino]acetic acid |
| (n-methyl-1-phenylformamido)acetic acid |
| AKOS000127141 |
| NCGC00247408-01 |
| hippuric acid, beta-methyl- |
| nsc 122438 |
| HMS2270E21 |
| AG-205/01796046 |
| 2-(n-methylbenzamido)acetic acid |
| PKCSYDDSNIJRIX-UHFFFAOYSA-N |
| DTXSID8062527 |
| benzoylsarkosin |
| SCHEMBL2282162 |
| n-methyl hippuric acid |
| STR05560 |
| mfcd00144940 |
| W18743 |
| A877511 |
| CAA56834 |
| CS-0215905 |
| Z85895238 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Moreover, by dosing with the two urinary metabolites of xylene, methylhippuric (MHAs) and mercapturic acids (MBAs), this study points toward a causal relationship between the cochleotoxic effects and potential reactive intermediates arising from the biotransformation of the parent molecules." | ( Ototoxicity of the three xylene isomers in the rat. Burgart, M; Campo, P; Cossec, B; Lataye, R; Maguin, K; Waniusiow, D, ) | 0.13 |
| Role | Description |
|---|---|
| EC 1.1.1.21 (aldehyde reductase) inhibitor | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| N-acylglycine | An N-acyl-amino acid in which amino acid specified is glycine. |
| monocarboxylic acid | An oxoacid containing a single carboxy group. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| chromobox protein homolog 1 | Homo sapiens (human) | Potency | 6.3096 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member B1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 23.0000 | 0.0004 | 1.8773 | 10.0000 | AID34965 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID34965 | Inhibitory activity against aldose reductase in rat lens | 1991 | Journal of medicinal chemistry, Jul, Volume: 34, Issue:7 | Relative structure-inhibition analyses of the N-benzoyl and N-(phenylsulfonyl) amino acid aldose reductase inhibitors. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (11.11) | 18.7374 |
| 1990's | 3 (33.33) | 18.2507 |
| 2000's | 1 (11.11) | 29.6817 |
| 2010's | 3 (33.33) | 24.3611 |
| 2020's | 1 (11.11) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.34) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 10 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||