Livestock Metabolome Database: Showing metabocard for Hippuric acid (LMDB00227)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:09 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00227

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hippuric acid

Description

Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. 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. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air. Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876 , 8734460 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benzamidoacetic acid	ChEBI
Benzamidoessigsaeure	ChEBI
Benzoylaminoacetic acid	ChEBI
Benzoylaminoessigsaeure	ChEBI
Hippurate	ChEBI
Hippursaeure	ChEBI
Phenylcarbonylaminoacetic acid	ChEBI
N-Benzoylglycine	Kegg
Benzamidoacetate	Generator
Benzoylaminoacetate	Generator
Phenylcarbonylaminoacetate	Generator
Hippate	Generator
Hippic acid	Generator
(Benzoylamino)-acetate	HMDB
(Benzoylamino)-acetic acid	HMDB
2-Benzamidoacetate	HMDB
2-Benzamidoacetic acid	HMDB
Benzoylglycine	HMDB
N-Benzoylglycinate	HMDB
Hippuric acid	HMDB

Chemical Formula

C₉H₉NO₃

Average Molecular Weight

179.1727

Monoisotopic Molecular Weight

179.058243159

IUPAC Name

2-(phenylformamido)acetic acid

Traditional Name

hippuric acid

CAS Registry Number

495-69-2

SMILES

OC(=O)CNC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)

InChI Key

QIAFMBKCNZACKA-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
Benzoyl
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:18089 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	0.23	ALOGPS
logP	0.53	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	-1.3	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	46.12 m³·mol⁻¹	ChemAxon
Polarizability	17.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0930000000-6f50aaca6d403e269682	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0a4i-5930000000-166d57ae498305a4eee9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-4920000000-358e012cae8853105371	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-8900000000-01e7057139a995115ddb	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0il0-9700000000-5eb7d5acc34cdb44f3e0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-6f50aaca6d403e269682	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-5930000000-166d57ae498305a4eee9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-4920000000-358e012cae8853105371	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-2910000000-19b240c27664cf096501	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-b1d771fba596fcbf4d44	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-3f2da6ec78f21732afea	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9810000000-58ac2f50544c1db5247f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0059-1900000000-412e9313d23685caab38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-004i-9100000000-cc560a494407b3c33abb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-004i-9200000000-103f81d635660cdb0aa0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a6r-8900000000-734176188abc8a1dd766	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-7f332f3c98391a276547	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-003r-2900000000-a8b444dcb0522a2aab6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9200000000-fc8a26847a77460ed21a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a6r-9000000000-9c160b377301023f1df2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-7f332f3c98391a276547	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-003r-2900000000-a8b444dcb0522a2aab6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9200000000-d20e52137daf3db2f638	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a6r-9000000000-1beabd6a9820b379f52f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0900000000-fae7f8c300bf6943f8d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-003r-0900000000-5d25dcc019489d867073	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-003r-0900000000-ef98916bdf0fc8627083	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0900000000-cbfff04acbf0c95d7e30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-65954d58bf9851d84f75	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-730b49f058aae1303aba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9500000000-2707fadcc633cb9d989c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8040a946088ae227b41e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2900000000-48c46f688fb318e3a7ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-4ded9b0d44ce0068065d	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-5900000000-99084c1783177c807011	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Kidney perfusate
Milk
Plasma
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23738862	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25828073	details
Serum	Detected and Quantified	42.7517 +/- 15.0181 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	38.5843 +/- 17.5336 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	24.0301 +/- 8.6033 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	46.1428 +/- 25.4726 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	56.7555 +/- 18.6603 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	38.9701 +/- 16.1639 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	26.3249 +/- 9.4343 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.9543 +/- 13.2227 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	43.0506 +/- 23.4245 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	27.9426 +/- 10.0945 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	42.9706 +/- 15.5802 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.2422 +/- 15.1076 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	44.3076 +/- 13.3017 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	54.737 +/- 32.3114 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	42.3491 +/- 16.4259 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	47.679 +/- 11.5947 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	37.716 +/- 18.2185 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	21.6798 +/- 17.3753 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	36.6726 +/- 13.3653 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	43.4418 +/- 30.421 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected and Quantified	1375 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected and Quantified	685 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22059599	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	24696864	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000714

FooDB ID

FDB001819

Phenol Explorer ID

Not Available

KNApSAcK ID

C00030483

BiGG ID

Not Available

BioCyc ID

CPD-425

METLIN ID

1301

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Amorim LC, Alvarez-Leite EM: Determination of o-cresol by gas chromatography and comparison with hippuric acid levels in urine samples of individuals exposed to toluene. J Toxicol Environ Health. 1997 Mar;50(4):401-7. [9120876 ]
Niwa T: Organic acids and the uremic syndrome: protein metabolite hypothesis in the progression of chronic renal failure. Semin Nephrol. 1996 May;16(3):167-82. [8734460 ]

Showing metabocard for Hippuric acid (LMDB00227)

Structure for LMDB00227 (Hippuric acid)