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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:58 UTC

HMDB ID

HMDB0000714

Secondary Accession Numbers

HMDB0062583
HMDB00714
HMDB62583

Metabolite Identification

Common Name

Hippuric acid

Description

Hippuric acid is an acyl glycine formed from the conjugation of benzoic acid 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 into benzoic acid which is then converted into 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 into aromatic compounds including ortho-cresol, which is not found in the urine of nonexposed individuals in a significant amount. 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 ). Hippuric acid has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Hippuric acid is also found to be associated with phenylketonuria, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism. Hippuric acid is an endogenous phenolic acid metabolite detected after the consumption of whole grain.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.374  -0.938   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.293  -0.938   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.708   1.372   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.293  -2.478   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.627  -0.168   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12   13                                                  
CONECT   11    7                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

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

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)
Coma (HMDB: HMDB0000714)

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000714)
Psychosis (HMDB: HMDB0000714)

Respiratory system disorder

Pulmonary disorder

Lung Cancer (HMDB: HMDB0000714)

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0000714)
Uremia (HMDB: HMDB0000714)
Chronic kidney disease (HMDB: HMDB0000714)

Poisoning

Paraquat poisoning (HMDB: HMDB0000714)

Observation

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0000714)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8412012)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 9439441)
Saliva (PMID: 22308371)
Breast milk (HMDB: HMDB0000714)
Cerebrospinal fluid (HMDB: HMDB0000714)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000714)
Extracellular (HMDB: HMDB0000714)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0000714)

Enteral

Ingestion (HMDB: HMDB0000714)

Source

Exogenous

Exogenous (HMDB: HMDB0000714)

Food

Food (HMDB: HMDB0000714)
Legumes (HMDB: HMDB0000714)

Animal origin

Poultry

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)

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)

Vegetables (HMDB: HMDB0000714)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000714)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000714)

Tea

Tea products (HMDB: HMDB0000714)

Fat and oil

Olive oil (HMDB: HMDB0000714)

Fruit

Fruits (HMDB: HMDB0000714)

Berry

American cranberry (FooDB: FOOD00192)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000714)

Nut

Nuts (HMDB: HMDB0000714)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0000714)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000714)

Plant

Plant (HMDB: HMDB0000714)

Microbe

Microbe (HMDB: HMDB0000714)
Eubacterium (HMDB: HMDB0000714)
Faecalibacterium prausnitzii (HMDB: HMDB0000714)
Ruminococcus (HMDB: HMDB0000714)
Clostridium (HMDB: HMDB0000714)
Actinomycetaceae (HMDB: HMDB0000714)

Process

Not Available

Role

Biological role

Indirect biological role

Metabotoxin

Uremic toxin (HMDB: HMDB0000714)
Uremic toxin (HMDB: HMDB0000714)

Industrial application

Agriculture

Pesticide (HMDB: HMDB0000714)

Pharmaceutical industry

Biomarker

Phenylketonuria (MarkerDB: MDB00000231)
Paraquat poisoning (MarkerDB: MDB00000231)
Uremia (MarkerDB: MDB00000231)
Argininosuccinic aciduria (MarkerDB: MDB00000231)

Physical Properties

State

Solid

Experimental Molecular 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)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	148.226	30932474
[M-H]-	MetCCS_train_neg	139.716	30932474
[M+H]+	Baker	146.818	30932474
[M-H]-	Not Available	143.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000293
[M+H]+	Not Available	146.818	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000293

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.18 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.691	31661259
DarkChem	[M+H]+	139.691	31661259
DarkChem	[M-H]-	136.137	31661259
DarkChem	[M-H]-	136.137	31661259
AllCCS	[M+H]+	138.327	32859911
AllCCS	[M-H]-	137.395	32859911
DeepCCS	[M+H]+	135.779	30932474
DeepCCS	[M-H]-	133.314	30932474
DeepCCS	[M-2H]-	169.01	30932474
DeepCCS	[M+Na]+	143.728	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	134.1	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	139.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hippuric acid	OC(=O)CNC(=O)C1=CC=CC=C1	2730.7	Standard polar	33892256
Hippuric acid	OC(=O)CNC(=O)C1=CC=CC=C1	1636.8	Standard non polar	33892256
Hippuric acid	OC(=O)CNC(=O)C1=CC=CC=C1	1823.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hippuric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC=C1	1873.5	Semi standard non polar	33892256
Hippuric acid,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CC=C1	1807.8	Semi standard non polar	33892256
Hippuric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C	1800.4	Semi standard non polar	33892256
Hippuric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C	1830.7	Standard non polar	33892256
Hippuric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C	2100.7	Standard polar	33892256
Hippuric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC=C1	2115.2	Semi standard non polar	33892256
Hippuric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CC=C1	2031.7	Semi standard non polar	33892256
Hippuric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2276.5	Semi standard non polar	33892256
Hippuric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2222.0	Standard non polar	33892256
Hippuric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2365.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0930000000-6f50aaca6d403e269682	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-MS (1 TMS)	splash10-0a4i-5930000000-166d57ae498305a4eee9	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-MS (2 TMS)	splash10-0a4i-4920000000-358e012cae8853105371	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid EI-B (Non-derivatized)	splash10-0a6r-8900000000-01e7057139a995115ddb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid EI-B (Non-derivatized)	splash10-0il0-9700000000-5eb7d5acc34cdb44f3e0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid EI-B (Non-derivatized)	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-EI-TOF (Non-derivatized)	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-6f50aaca6d403e269682	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-MS (Non-derivatized)	splash10-0a4i-5930000000-166d57ae498305a4eee9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-MS (Non-derivatized)	splash10-0a4i-4920000000-358e012cae8853105371	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-EI-TOF (Non-derivatized)	splash10-0a4i-2910000000-19b240c27664cf096501	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hippuric acid GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-b1d771fba596fcbf4d44	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hippuric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-3f2da6ec78f21732afea	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hippuric acid GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9810000000-58ac2f50544c1db5247f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hippuric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hippuric acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hippuric acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hippuric acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-5900000000-99084c1783177c807011	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-0059-1900000000-412e9313d23685caab38	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-004i-9100000000-cc560a494407b3c33abb	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-004i-9200000000-103f81d635660cdb0aa0	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid EI-B (VARIAN MAT-44) , Positive-QTOF	splash10-0a6r-8900000000-734176188abc8a1dd766	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid EI-B (HITACHI RMU-6E) , Positive-QTOF	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-004i-0900000000-7f332f3c98391a276547	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-003r-2900000000-a8b444dcb0522a2aab6d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-9200000000-fc8a26847a77460ed21a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a6r-9000000000-9c160b377301023f1df2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ , negative-QTOF	splash10-004i-0900000000-7f332f3c98391a276547	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ , negative-QTOF	splash10-003r-2900000000-a8b444dcb0522a2aab6d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ , negative-QTOF	splash10-004i-9200000000-d20e52137daf3db2f638	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ , negative-QTOF	splash10-0a6r-9000000000-1beabd6a9820b379f52f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-IT , negative-QTOF	splash10-001i-0900000000-fae7f8c300bf6943f8d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid LC-ESI-QTOF , negative-QTOF	splash10-003r-0900000000-5d25dcc019489d867073	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid , negative-QTOF	splash10-003r-0900000000-ef98916bdf0fc8627083	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hippuric acid , positive-QTOF	splash10-0a4i-0900000000-cbfff04acbf0c95d7e30	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hippuric acid 10V, Positive-QTOF	splash10-001i-0900000000-65954d58bf9851d84f75	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hippuric acid 20V, Positive-QTOF	splash10-001i-0900000000-730b49f058aae1303aba	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hippuric acid 40V, Positive-QTOF	splash10-056r-9500000000-2707fadcc633cb9d989c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hippuric acid 10V, Negative-QTOF	splash10-004i-0900000000-8040a946088ae227b41e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hippuric acid 20V, Negative-QTOF	splash10-004i-2900000000-48c46f688fb318e3a7ba	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hippuric acid 40V, Negative-QTOF	splash10-004i-9300000000-4ded9b0d44ce0068065d	2015-04-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Kidney
Liver
Placenta
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.0 (0.0-5.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26264776	details
Blood	Detected and Quantified	16.74 +/- 11.16 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected and Quantified	1.000-28.00 uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected and Quantified	<27.933 uM	Adult (>18 years old)	Both	Normal	12675874	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Breast Milk	Detected and Quantified	7.8 +/- 4.2 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.23 (0.11-0.12) uM	Children (1-13 years old)	Both	Normal	9439441	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected and Quantified	0.234 (0.0446-0.686) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	217 (28-610) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	49-150 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	257(20-770) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	6321058	details
Urine	Detected but not Quantified	Not Quantified	Adult (24-38years old)	Not Specified	Normal	20971021	details
Urine	Detected and Quantified	871.36 +/- 1024.84 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	2026685	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20573794	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23657156	details
Urine	Detected and Quantified	57.901 +/- 74.698 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	27.92-932.66 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22800120	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	1.51-213 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	28.67(1.33-213.6) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	96-398 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	60.00(3.20-207.3) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	837.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9625050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	15740018	details
Urine	Detected and Quantified	258.645 +/- 22.969 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	26910390	details
Urine	Detected and Quantified	230.81 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected and Quantified	100.0 +/- 10.6 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12663291	details
Urine	Detected and Quantified	290 (170-390) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	12.5-56.2 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	13.5-131.5 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	19-63 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	31.7-157.4 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	16939360	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	16939360	details
Urine	Detected and Quantified	175.9 +/- 124.3 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	17474139	details
Urine	Detected and Quantified	207.3 +/- 118.8 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17474139	details
Urine	Detected and Quantified	<969.8 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	298.5 +/- 276.8 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15992788	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22148915	details
Urine	Detected and Quantified	64-145 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	140 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	22623390	details
Urine	Detected and Quantified	188 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	22623390	details
Urine	Detected and Quantified	229 (19-622) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	27.57 (16.64-44.00) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	189.34 (60.44 – 521.82) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Lorena Ivona ŞTEF...	details
Urine	Detected and Quantified	42.8 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected and Quantified	205.479 +/- 143.911 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	486.68 +/- 344.36 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected and Quantified	1379.888 +/- 625.698 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	21799048	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Cardiosvacular risk	22887155	details
Urine	Detected and Quantified	115.692 +/- 143.792 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	230.898 +/- 341.217 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22800120	details
Urine	Detected and Quantified	88.2 umol/mmol creatinine	Adult (>18 years old)	Both	Paraquat poisoning	9625050	details
Urine	Detected and Quantified	128.367 +/- 12.974 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	26910390	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	22148915	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	473.0 +/- 617.0 umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	18953024	details
Urine	Detected and Quantified	193.62 (5.52 – 731.67) umol/mmol creatinine	Adult (>18 years old)	Both	Type 1 diabetes Mellitus	Lorena Ivona ŞTEF...	details
Urine	Detected and Quantified	32.5 +/- 3.1 umol/mmol creatinine	Adult (>18 years old)	Both	3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency	19551947	details
Urine	Detected and Quantified	20.5 +/- 0.7 umol/mmol creatinine	Adult (>18 years old)	Both	Argininosuccinic aciduria (ASL)	19551947	details
Urine	Detected and Quantified	38.9 +/- 4.5 umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	19551947	details
Urine	Detected and Quantified	99.8 +/- 11.8 umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	19551947	details
Urine	Detected and Quantified	108.3 +/- 3.4 umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	19551947	details
Urine	Detected and Quantified	96.2 +/- 6.5 umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	19551947	details
Urine	Detected and Quantified	50.2 +/- 4.4 umol/mmol creatinine	Adult (>18 years old)	Both	Phenylketonuria	19551947	details
Urine	Detected and Quantified	234.1 +/- 15.3 umol/mmol creatinine	Adult (>18 years old)	Both	Maple syrup urine disease	19551947	details
Urine	Detected and Quantified	299.437 +/- 474.323 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Uremia
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ] Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Paraquat poisoning
Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed:9625050 ]
Lung Cancer
Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Diabetes mellitus type 1
(). Lorena Ivona ŞTEFAN, Alina NICOLESCU, Simona POPA, Maria MOŢA, Eugenia KOVACS and Calin DELEANU. 1H-NMR URINE METABOLIC PROFILING IN TYPE 1 DIABETES MELLITUS. Rev. Roum. Chim., 2010, 55(11-12), 1033-1037 . .
Argininosuccinic aciduria
Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Propionic acidemia
Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Tyrosinemia I
Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Phenylketonuria
Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Maple syrup urine disease
Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Colorectal cancer
Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Schizophrenia
Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
Obesity
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]

Associated OMIM IDs

266600 (Crohn's disease)
211980 (Lung Cancer)
222100 (Diabetes mellitus type 1)
207900 (Argininosuccinic aciduria)
606054 (Propionic acidemia)
276700 (Tyrosinemia I)
261600 (Phenylketonuria)
248600 (Maple syrup urine disease)
610247 (Eosinophilic esophagitis)
114500 (Colorectal cancer)
181500 (Schizophrenia)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

BGLY

MarkerDB ID

MDB00000231

Good Scents ID

Not Available

References

Synthesis Reference

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

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed:9625050 ]
Angerer J, Kassebart V, Szadkowski D, Lehnert G: [Occupational chronic exposure to organic solvents. III. Gas-chromatographic determination of hippuric acid in serum (author's transl)]. Int Arch Arbeitsmed. 1975;34(3):199-207. [PubMed:1184200 ]
Akira K, Hashimoto T: Hippuric acid test using 13C-labelling and NMR spectroscopy. Clin Chem Lab Med. 2001 Mar;39(3):215-7. [PubMed:11350017 ]
Pelclova D, Cerna M, Pastorkova A, Vrbikova V, Prochazka B, Hurychova D, Dlaskova Z, Hornychova M: Study of the genotoxicity of toluene. Arch Environ Health. 2000 Jul-Aug;55(4):268-73. [PubMed:11005432 ]
Rutner M, Fitzek J, Jahnel-Kracht H, Otto J, Krause W: [Therapy of rheumatic disease with a hydroxyethylsalicylate gel. Results of 2 clinical studies of effectiveness and bioavailability]. Fortschr Med. 1995 Mar 20;113(8):111-3. [PubMed:7759034 ]
Bjorkman L, McLean C, Steen G: Organic acids in urine from human newborns. Clin Chem. 1976 Jan;22(1):49-52. [PubMed:1245060 ]
Caldwell J, Moffatt JR, Smith RL: Post-mortem survival of hippuric acid formation in rat and human cadaver tissue samples. Xenobiotica. 1976 May;6(5):275-80. [PubMed:936647 ]
Ukai H, Takada S, Inui S, Imai Y, Kawai T, Shimbo S, Ikeda M: Occupational exposure to solvent mixtures: effects on health and metabolism. Occup Environ Med. 1994 Aug;51(8):523-9. [PubMed:7951776 ]
Sebekova K, Lajdova I, Spustova V, Opatrny K Jr: Comparison of creatinine, hippuric acid, 5-hydroxyindoleacetic acid, serotonin, and pseudouridine concentrations in blood withdrawn from vein and arteriovenous fistula of uremic patients on maintenance hemodialysis. Artif Organs. 1991 Oct;15(5):434-5. [PubMed:1741691 ]
Pickert A, Bauerle A, Liebich HM: Determination of hippuric acid and furanic acid in serum of dialysis patients and control persons by high-performance liquid chromatography. J Chromatogr. 1989 Oct 27;495:95-104. [PubMed:2613830 ]
Mulder TP, Rietveld AG, van Amelsvoort JM: Consumption of both black tea and green tea results in an increase in the excretion of hippuric acid into urine. Am J Clin Nutr. 2005 Jan;81(1 Suppl):256S-260S. [PubMed:15640488 ]
Porter RD, Cathcart-Rake WF, Wan SH, Whittier FC, Grantham JJ: Secretory activity and aryl acid content of serum, urine, and cerebrospinal fluid in normal and uremic man. J Lab Clin Med. 1975 May;85(5):723-31. [PubMed:1168235 ]
Lof A, Hansen SH, Naslund P, Steiner E, Wallen M, Hjelm EW: Relationship between uptake and elimination of toluene and debrisoquin hydroxylation polymorphism. Clin Pharmacol Ther. 1990 Mar;47(3):412-7. [PubMed:2311341 ]
Kirshon B, Mari G, Moise KJ Jr: Indomethacin therapy in the treatment of symptomatic polyhydramnios. Obstet Gynecol. 1990 Feb;75(2):202-5. [PubMed:2405320 ]
Beving H, Olsson U, Bemgard A, Kristensson J, Palmborg J, Sollenberg J: High-performance liquid chromatographic analysis of hippuric acid in human blood plasma. J Chromatogr. 1990 Oct 26;532(1):45-53. [PubMed:2079538 ]
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. [PubMed:8734460 ]
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. [PubMed:9120876 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Pallister T, Jackson MA, Martin TC, Zierer J, Jennings A, Mohney RP, MacGregor A, Steves CJ, Cassidy A, Spector TD, Menni C: Hippurate as a metabolomic marker of gut microbiome diversity: Modulation by diet and relationship to metabolic syndrome. Sci Rep. 2017 Oct 20;7(1):13670. doi: 10.1038/s41598-017-13722-4. [PubMed:29057986 ]
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Enzymes

Enzyme Details

1. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

Benzoyl-CoA + Glycine → Coenzyme A + Hippuric acid	details
Benzoic acid → Hippuric acid	details

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

4. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Showing metabocard for Hippuric acid (HMDB0000714)

MOL for HMDB0000714 (Hippuric acid)

3D MOL for HMDB0000714 (Hippuric acid)

3D SDF for HMDB0000714 (Hippuric acid)

3D-SDF for HMDB0000714 (Hippuric acid)

PDB for HMDB0000714 (Hippuric acid)

3D PDB for HMDB0000714 (Hippuric acid)

SMILES for HMDB0000714 (Hippuric acid)

INCHI for HMDB0000714 (Hippuric acid)

Structure for HMDB0000714 (Hippuric acid)

3D Structure for HMDB0000714 (Hippuric acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions