Milk Composition Database: Showing metabocard for Hippuric acid (BMDB0000714)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:21 UTC

Update Date

2020-06-04 20:23:27 UTC

MCDB ID

BMDB0000714

Secondary Accession Numbers

BMDB00714

Metabolite Identification

Common Name

Hippuric acid

Description

Hippuric acid, also known as N-benzoylglycine or hippurate, 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. Hippuric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Hippuric acid is a potentially toxic compound. Hippuric acid has been found to be associated with several diseases known as uremia, ulcerative colitis, colorectal cancer, and eosinophilic esophagitis; also hippuric acid has been linked to the inborn metabolic disorders including tyrosinemia I.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	187 - 191 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.75 mg/mL	Not Available
LogP	0.31	HANSCH,C ET AL. (1995)

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	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 - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0a4i-5930000000-166d57ae498305a4eee9	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-4920000000-358e012cae8853105371	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-8900000000-01e7057139a995115ddb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0il0-9700000000-5eb7d5acc34cdb44f3e0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-6f50aaca6d403e269682	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-5930000000-166d57ae498305a4eee9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-4920000000-358e012cae8853105371	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-2910000000-19b240c27664cf096501	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-b1d771fba596fcbf4d44	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-3f2da6ec78f21732afea	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9810000000-58ac2f50544c1db5247f	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0059-1900000000-412e9313d23685caab38	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-004i-9100000000-cc560a494407b3c33abb	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-004i-9200000000-103f81d635660cdb0aa0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a6r-8900000000-734176188abc8a1dd766	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-7f332f3c98391a276547	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-003r-2900000000-a8b444dcb0522a2aab6d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9200000000-fc8a26847a77460ed21a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a6r-9000000000-9c160b377301023f1df2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-7f332f3c98391a276547	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-003r-2900000000-a8b444dcb0522a2aab6d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9200000000-d20e52137daf3db2f638	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a6r-9000000000-1beabd6a9820b379f52f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0900000000-fae7f8c300bf6943f8d5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-003r-0900000000-5d25dcc019489d867073	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-003r-0900000000-ef98916bdf0fc8627083	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0900000000-cbfff04acbf0c95d7e30	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-65954d58bf9851d84f75	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-730b49f058aae1303aba	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9500000000-2707fadcc633cb9d989c	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8040a946088ae227b41e	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2900000000-48c46f688fb318e3a7ba	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-4ded9b0d44ce0068065d	2015-04-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-5900000000-99084c1783177c807011	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 23738862	details
Detected but not Quantified	Not Applicable	PMID: 23182357	details
Detected but not Quantified	Not Applicable	PMID: 25087032	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	65 +/- 5 uM	PMID: 30994344	details
Detected and Quantified	69 +/- 9 uM	PMID: 30994344	details
Detected and Quantified	72 +/- 5 uM	PMID: 30994344	details
Detected and Quantified	67 +/- 4 uM	PMID: 30994344	details
Detected and Quantified	227 +/- 39 uM	PMID: 29642378	details
Detected and Quantified	165 +/- 33 uM	PMID: 29642378	details
Detected and Quantified	113 +/- 33 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0000714

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hippuric_acid

METLIN ID

1301

PubChem Compound

464

PDB ID

Not Available

ChEBI ID

18089

References

Synthesis Reference

Ingersoll, A. W.; Barcock, S. H. Hippuric acid. Organic Syntheses (1932), XII 40-2.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Hippuric acid (BMDB0000714)

Structure for BMDB0000714 (Hippuric acid)