4-methylhippuric acid profile

4-Methylhippuric acid (4-MHA) is a urinary metabolite of toluene, a common industrial solvent. It is formed in the liver through the conjugation of toluene with glycine. 4-MHA is used as a biomarker of toluene exposure. Elevated levels of 4-MHA in urine indicate recent exposure to toluene. Studies have shown that 4-MHA is a potential indicator of toluene-induced neurotoxicity. The levels of 4-MHA in urine are also used to monitor the effectiveness of treatments for toluene addiction. 4-MHA is synthesized in the laboratory through the reaction of toluene with glycine in the presence of a catalyst. The synthesis of 4-MHA has been used in research to study the metabolism of toluene. 4-MHA is a relatively stable compound and can be easily measured in urine samples using various analytical techniques. This makes it a valuable biomarker for monitoring toluene exposure.'

4-methylhippuric acid: urinary metabolite of p-xylene [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

p-methylhippuric acid : An N-acylglycine in which the acyl group is specified as 4-methylbenzoyl. [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	97479
CHEMBL ID	274877
CHEBI ID	68552
SCHEMBL ID	1285723
MeSH ID	M0098729

Synonym
n-(4-methylbenzoyl)glycine
p-toluric acid
nsc126814
27115-50-0
p-methylhippuric acid
hippuric acid, p-methyl-
glycine, n-(4-methylbenzoyl)-
nsc-126814
DIVK1C_002084
CDS1_001044
OPREA1_357822
4-methylhippuric acid, 98%
MAYBRIDGE1_005796
M-3784
inchi=1/c10h11no3/c1-7-2-4-8(5-3-7)10(14)11-6-9(12)13/h2-5h,6h2,1h3,(h,11,14)(h,12,13
4-methylhippuric acid
HMS557P10
CHEMBL274877 ,
chebi:68552 ,
2-[(4-methylbenzoyl)amino]acetic acid
n-(p-toluoyl)glycine
T0313
(4-methyl-benzoylamino)-acetic acid
bdbm50016613
AKOS001043926
2-[(4-methylphenyl)formamido]acetic acid
STK696186
n-[(4-methylphenyl)carbonyl]glycine
nsc 126814
para-methylhippuric acid
einecs 248-231-8
unii-9qox0dsk6f
9qox0dsk6f ,
2-(4-methylbenzamido)acetic acid
F1130-0053
4-methyl hippuric acid
n-(p-methylbenzoyl)glycine
FT-0619087
BBL025689
(4-methylbenzoylamino)acetic acid
(((4-methylphenyl)carbonyl)amino)acetic acid
toluric acid, p-
p-toluoylglycine
SCHEMBL1285723
n-(p-toluoyl)-glycine
[(4-methylbenzoyl)amino]acetic acid #
DTXSID00181580
sr-01000514107
mfcd00020449
4_methylhippuricacid
SR-01000514107-1
((4-methylbenzoyl)amino)acetic acid
Z56899118
glycine,n-(4-methylbenzoyl)-
Q22132817
EN300-03936
[(4-methylbenzoyl)amino]acetic acid
D95330
n-(4-methylbenzoyl)glycine; p-methylhippuric acid; n-(p-toluoyl)glycine
4-methylhippuricacid
2-(4-methylbenzamido)aceticacid
CS-0137678
4-methylhippuric acid polymorph i
2-[(4-methylbenzoyl)amino]ethanoic acid

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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.
[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	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Aldo-keto reductase family 1 member B1	Rattus norvegicus (Norway rat)	IC50 (µMol)	220.0000	0.0004	1.8773	10.0000	AID34939
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID34939	Inhibition of aldose reductase from rat lens. Value ranges from 110 - 430	1989	Journal of medicinal chemistry, May, Volume: 32, Issue:5	Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety.
AID388272	Activity of rat recombinant peptidylglycine alpha-amidating monooxygenase assessed as stimulation of oxygen consumption	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
AID388273	Ratio of Vm(app) to Km(app) for rat recombinant peptidylglycine alpha-amidating monooxygenase	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
AID35127	Inhibition of partially purified aldose reductase obtained from rat lens (100 uM ); ND is No Data	1989	Journal of medicinal chemistry, May, Volume: 32, Issue:5	Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety.
AID388274	Ratio of Vm(app) to Km(app) for rat recombinant peptidylglycine alpha-amidating monooxygenase relative to hippuric acid	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	12 (50.00)	18.7374
1990's	3 (12.50)	18.2507
2000's	7 (29.17)	29.6817
2010's	1 (4.17)	24.3611
2020's	1 (4.17)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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	27 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
benzene [no description available]	2.02	1	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	9	14	N-acylglycine	human blood serum metabolite; uremic toxin
glycine [no description available]	2.39	2	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.01	1	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	3.22	6	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
mandelic acid SAMMA: mandelic acid condensation polymer	2.4	2	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	2.4	2	N-acylglycine	Daphnia magna metabolite
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.01	1	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	1.96	1	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	1.96	1	chloroethenes	inhalation anaesthetic; mouse metabolite
4-toluic acid 4-toluic acid: RN given refers to parent cpd; structure. p-toluic acid : A methylbenzoic acid in which the methyl substituent is located at position 4.	2.01	1	methylbenzoic acid
iodohippuric acid Iodohippuric Acid: An iodine-containing compound used in pyelography as a radiopaque medium. If labeled with radioiodine, it can be used for studies of renal function.. 2-iodohippuric acid : A member of the class of benzamides resulting from the formal condensation of the carboxy group of 2-iodobenzoic acid with the amino group of glycine.	2.04	1	benzamides; N-acylglycine; organoiodine compound
salicylurate salicylurate: RN given refers to parent cpd. salicyluric acid : An N-acylglycine in which the acyl group is specified as 2-hydroxybenzoyl.. salicylurate : A monocarboxylic acid anion that is the conjugate base of salicyluric acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.04	1	N-acylglycine; secondary carboxamide	human xenobiotic metabolite; uremic toxin
aceturic acid aceturic acid: structure. N-acetylglycine : An N-acylglycine where the acyl group is specified as acetyl.	2.04	1	N-acetyl-amino acid; N-acylglycine	human metabolite
phenylglyoxylic acid phenylglyoxylic acid: styrene metabolite. phenylglyoxylic acid : A 2-oxo monocarboxylic acid that is glyoxylic acid in which the aldehyde hydrogen is substituted by a phenyl group.	1.97	1	2-oxo monocarboxylic acid	biomarker; human xenobiotic metabolite
n-benzyloxycarbonylglycine N-benzyloxycarbonylglycine: structure given in first source. N-benzyloxycarbonylglycine : A derivative of glycine having a benzyloxycarbonyl protecting group attached to the nitrogen.	2.04	1	N-acylglycine
decyltrimethylammonium decyltrimethylammonium ion : A quarternary ammonium cation having one decyl and three methyl substituents around the central nitrogen.	1.98	1	quaternary ammonium ion
4-nitrohippuric acid 4-nitrohippuric acid: major metabolite of 4-nitrobenzoic acid	2.4	2
furoylglycine furoylglycine: structure given in first source. N-(2-furoyl)glycine : A glycine derivative that is the carboxamide obtained by the formal condensation of the amino group of glycine with 2-furoic acid.	2.04	1	furans; N-acylglycine	human metabolite
4-chlorohippuric acid 4-chlorohippuric acid: metabolite of zomepirac; RN given refers to parent cpd	2.4	2
thiophenoxyacetic acid thiophenoxyacetic acid: structure	2.04	1
salicylhydroxamic acid [no description available]	2.04	1	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
phenylacetylglycine phenylacetylglycine : A N-acylglycine that is glycine substituted on nitrogen with a phenylacetyl group.	2.04	1	monocarboxylic acid amide; monocarboxylic acid; N-acylglycine	human metabolite; mouse metabolite
nicotinuric acid nicotinuric acid: RN given refers to parent cpd. N-nicotinoylglycine : An N-acylglycine having nicotinoyl as the acyl substituent.	2.04	1	N-acylglycine	human urinary metabolite
n-benzoylalanine, (dl-ala)-isomer [no description available]	1.97	1	alanine derivative; N-acyl-amino acid	metabolite
benzoylpropionic acid benzoylpropionic acid: structure in first source. 4-oxo-4-phenylbutyric acid : A 4-oxo monocarboxylic acid that is butyric acid bearing oxo and phenyl substituents at position 4.	2.04	1	4-oxo monocarboxylic acid	hapten
boc-glycine BOC-glycine: RN given refers to parent cpd	2.04	1
n-benzylglycine [no description available]	2.04	1
2-methylhippuric acid 2-methylhippuric acid: urinary metabolite of o-xylene. o-methylhippuric acid : An N-acylglycine that is the ortho-methyl derivative of hippuric acid.	3.92	13	N-acylglycine	metabolite
hippuryl-glycyl-glycine hippuryl-glycyl-glycine: RN given refers to parent cpd; N1 from 9th CI Form Index	2.04	1
3-methylhippuric acid 3-methylhippuric acid: urinary metabolite of m-xylene. m-methylhippuric acid : An N-acylglycine that is the 3-methyl derivative of hippuric acid.	4.05	15	N-acylglycine	metabolite
4-methyoxybenzoyl-n-glycine [no description available]	2.4	2	N-acylglycine
2-naphthoylglycine 2-naphthoylglycine: RN not in Chemline 8/18/82	1.97	1
4-hydroxyhippuric acid p-hydroxyhippuric acid : An N-acylglycine that is the 4-hydroxy derivative of hippuric acid.	2.04	1	N-acylglycine	human blood serum metabolite
sorbinil sorbinil: aldose reductase inhibitor. sorbinil : An azaspiro compound having a monofluoro-substituted chromane skeleton spiro-linked to an imidazolidinedione ring.	1.97	1	azaspiro compound; chromanes; imidazolidinone; organofluorine compound; oxaspiro compound	antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor
cinnamoylglycine cinnamoylglycine: structure given in first source. N-cinnamoylglycine : An N-acylglycine in which the acyl group is specified as (2E)-3-phenylprop-2-enoyl (cinnamoyl).	2.04	1	N-acylglycine	metabolite
2-aminohippuric acid [no description available]	2.4	2	N-acylglycine
fenretinide Fenretinide: A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.. 4-hydroxyphenyl retinamide : A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.	2.04	1	monocarboxylic acid amide; retinoid	antineoplastic agent; antioxidant
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.01	1	phosphatidylcholine(1+)
dioleoylphosphatidic acid dioleoylphosphatidic acid: RN given refers to (Z)-isomer. dioleoyl phosphatidic acid : A phosphatidic acid in which the phosphatidyl acyl groups are both oleoyl.	2.01	1	1,2-bis(octadec-9-enoyl)phosphatidic acid
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	2	1
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.92	4	1,2-diacyl-sn-glycero-3-phosphocholine
chitosan [no description available]	2.31	1

Condition	Indicated	Relationship Strength	Studies	Trials
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	0	2.4	2	0
Diseases, Occupational [description not available]	0	2.66	3	0

4-methylhippuric acid

Description

Cross-References

Synonyms (64)

Roles (1)

Drug Classes (1)

Protein Targets (2)

Inhibition Measurements

Other Measurements

Bioassays (5)

Research

Studies (24)

Market Indicators

Research Demand Index: 16.39

Study Types