Milk Composition Database: Showing metabocard for 2-Methylhippuric acid (BMDB0011723)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:23:33 UTC

Update Date

2020-04-22 15:46:10 UTC

MCDB ID

BMDB0011723

Secondary Accession Numbers

BMDB11723

Metabolite Identification

Common Name

2-Methylhippuric acid

Description

2-Methylhippuric acid, also known as N-(O-toluoyl)glycine or N-(methylbenzoyl)-glycine, 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. 2-Methylhippuric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-8900000000-f3facdb25edf52b32bf5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-1921000000-99d8518c7ed8a7303750	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-2930000000-17087fd513ab1a3e48c8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1911000000-d30157f1d23d841dd7fa	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-3920000000-ffcf68f9d13b6ffa54c5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-8900000000-f3facdb25edf52b32bf5	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-1921000000-99d8518c7ed8a7303750	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-2930000000-17087fd513ab1a3e48c8	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1911000000-d30157f1d23d841dd7fa	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-3920000000-ffcf68f9d13b6ffa54c5	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-7900000000-a0e6f767778cd1dac471	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9210000000-a706f78bdfa3ab6b4a0a	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-964fdc6a530e3ced5e34	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-8b17a665175fbcba831b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-a9778b196de1304f3433	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014l-6900000000-8af38895fa1d5760b92d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-3900000000-a82d0267df099b7dfc4c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-1894a3131f12f0bc0630	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2900000000-3a52e728af0927d90d61	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0101-4900000000-be3581a92b3d98f72498	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-9200000000-ef2cb39cf678d6892d49	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-848582a82498a747b60c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2900000000-d8c8ac579c87ff465eb9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r6-9300000000-8f7a8b2f5617b2cda457	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-4900000000-ecfbd0d43eb964c79359	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-4946aff46366d89e59f0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-5671d4c535a6553aaf0d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-4900000000-71d856c475306586b490	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9700000000-e5cff62d21a3a704ee9c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a1e2bcbd969ecf85e4e5	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28342601	details

External Links

HMDB ID

HMDB0011723

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028406

KNApSAcK ID

Not Available

Chemspider ID

82742

KEGG Compound ID

C01586

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylhippuric acid

METLIN ID

Not Available

PubChem Compound

91637

PDB ID

Not Available

ChEBI ID

68455

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]

Showing metabocard for 2-Methylhippuric acid (BMDB0011723)

Structure for BMDB0011723 (2-Methylhippuric acid)