ChemFOnt: Showing chemical card for 2-Methylhippuric acid (CFc000007296)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:33 UTC

Chemfont ID

CFc000007296

Molecule Identification

Common Name

2-Methylhippuric acid

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(O-Toluoyl)glycine	ChEBI
O-Toluric acid	ChEBI
O-Tolate	Generator
O-Tolic acid	Generator
2-Methylhippate	Generator
2-Methylhippic acid	Generator
N-(2-Methylbenzoyl)-glycine	HMDB
N-(2-Methylbenzoyl)glycine	HMDB
N-(Methylbenzoyl)-glycine	HMDB
N-(Methylbenzoyl)glycine	HMDB
N-(O-Toluoyl)-glycine	HMDB
O-Methylhippuric acid	HMDB
Ortho-methylhippuric acid	HMDB
O-Methylhippate	HMDB
O-Methylhippic acid	HMDB
2-Methylhippuric acid	ChEBI

Chemical Formula

C₁₀H₁₁NO₃

Average Molecular Weight

193.1992

Monoisotopic Molecular Weight

193.073893223

IUPAC Name

2-[(2-methylphenyl)formamido]acetic acid

Traditional Name

methyl hippurate

CAS Registry Number

42013-20-7

SMILES

CC1=C(C=CC=C1)C(=O)NCC(O)=O

InChI Identifier

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)

InChI Key

YOEBAVRJHRCKRE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
O-toluamide
Toluamide
Benzoyl
Toluene
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:68455 )

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0011723)

Excreta

Biofluid or Excreta

Urine (PMID: 1912696)

Source

Endogenous

Endogenous (HMDB: HMDB0011723)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Biological role

Waste product (PMID: 35448883)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.6 g/L	ALOGPS
logP	0.66	ALOGPS
logP	1.04	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.16 m³·mol⁻¹	ChemAxon
Polarizability	19.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon