CHEBI:18089 - N-benzoylglycine

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ChEBI Name N-benzoylglycine
ChEBI ID CHEBI:18089
ChEBI ASCII Name N-benzoylglycine
Definition An N-acylglycine in which the acyl group is specified as benzoyl.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:14400, CHEBI:5725, CHEBI:12492, CHEBI:24595
Supplier Information ChemicalBook:CB0483177, eMolecules:478735, ZINC000006344064
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Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenolic compounds (such as in fruit juice, tea and wine). The phenols are first converted to benzoic acid, and then to hippuric acid and excreted in urine. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C, and decompose at about 240 °C. High concentrations of hippuric acid may also indicate a toluene intoxication; however, scientists have called this correlation into question because there are other variables that affect levels of hippuric acid. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.
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Formula C9H9NO3
Net Charge 0
Average Mass 179.17270
Monoisotopic Mass 179.05824
InChI 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)
InChIKey QIAFMBKCNZACKA-UHFFFAOYSA-N
SMILES OC(=O)CNC(=O)c1ccccc1
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): uremic toxin
A toxin that accumulates in patients with chronic kidney disease.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-benzoylglycine (CHEBI:18089) has role human blood serum metabolite (CHEBI:85234)
N-benzoylglycine (CHEBI:18089) has role uremic toxin (CHEBI:64584)
N-benzoylglycine (CHEBI:18089) is a N-acylglycine (CHEBI:16180)
N-benzoylglycine (CHEBI:18089) is conjugate acid of N-benzoylglycinate (CHEBI:606565)
Incoming α-hydroxyhippuric acid (CHEBI:68451) has functional parent N-benzoylglycine (CHEBI:18089)
2,3-dihydroxy-N-benzoylserine dimer (CHEBI:197975) has functional parent N-benzoylglycine (CHEBI:18089)
2-[(2-Aminobenzoyl)amino]propanoic acid (CHEBI:182145) has functional parent N-benzoylglycine (CHEBI:18089)
2-[(4-methoxyphenyl)formamido]acetic acid (CHEBI:189793) has functional parent N-benzoylglycine (CHEBI:18089)
2-Aminohippuric acid (CHEBI:165184) has functional parent N-benzoylglycine (CHEBI:18089)
2-{[(3,5-dimethoxyphenyl)(hydroxy)methylidene]amino}acetic acid (CHEBI:168859) has functional parent N-benzoylglycine (CHEBI:18089)
2-{[hydroxy(2,3,4-trimethoxyphenyl)methylidene]amino}acetic acid (CHEBI:189893) has functional parent N-benzoylglycine (CHEBI:18089)
2-{[hydroxy(2,4,6-trihydroxyphenyl)methylidene]amino}acetic acid (CHEBI:169106) has functional parent N-benzoylglycine (CHEBI:18089)
2-{[hydroxy(2-methoxyphenyl)methylidene]amino}acetic acid (CHEBI:189758) has functional parent N-benzoylglycine (CHEBI:18089)
2-{[hydroxy(3-methoxyphenyl)methylidene]amino}acetic acid (CHEBI:189778) has functional parent N-benzoylglycine (CHEBI:18089)
m-hydroxyhippuric acid (CHEBI:70824) has functional parent N-benzoylglycine (CHEBI:18089)
m-methylhippuric acid (CHEBI:68500) has functional parent N-benzoylglycine (CHEBI:18089)
p-hydroxyhippuric acid (CHEBI:71018) has functional parent N-benzoylglycine (CHEBI:18089)
Inducamide A (CHEBI:219064) has functional parent N-benzoylglycine (CHEBI:18089)
Inducamide B (CHEBI:219072) has functional parent N-benzoylglycine (CHEBI:18089)
Kaitocephalin (CHEBI:216599) has functional parent N-benzoylglycine (CHEBI:18089)
m-Chloro-hippuric acid (CHEBI:176504) has functional parent N-benzoylglycine (CHEBI:18089)
m-Trifluoromethylhippuric acid (CHEBI:185887) has functional parent N-benzoylglycine (CHEBI:18089)
Madurastatin B2 (CHEBI:182135) has functional parent N-benzoylglycine (CHEBI:18089)
Methenamine hippurate (CHEBI:6825) has functional parent N-benzoylglycine (CHEBI:18089)
methyl hippurate (CHEBI:70869) has functional parent N-benzoylglycine (CHEBI:18089)
N,N',N''-Tris(2,3-dihydroxybenzoyl)-O-L-seryl-O-L-seryl L-serine (CHEBI:182161) has functional parent N-benzoylglycine (CHEBI:18089)
N2,N6-bis(2,3-Dihydroxybenzoyl)-L-lysine (CHEBI:165185) has functional parent N-benzoylglycine (CHEBI:18089)
QMH (CHEBI:228410) has functional parent N-benzoylglycine (CHEBI:18089)
sivelestat (CHEBI:135704) has functional parent N-benzoylglycine (CHEBI:18089)
Sivelestat sodium hydrate (CHEBI:32133) has functional parent N-benzoylglycine (CHEBI:18089)
sodium 2-(125I)iodohippurate (CHEBI:134739) has functional parent N-benzoylglycine (CHEBI:18089)
sodium 2-(131I)iodohippurate (CHEBI:134740) has functional parent N-benzoylglycine (CHEBI:18089)
N-benzoylglycinate (CHEBI:606565) is conjugate base of N-benzoylglycine (CHEBI:18089)
IUPAC Name
N-benzoylglycine
Synonyms Sources
Benzamidoacetic acid ChemIDplus
Benzamidoessigsäure ChemIDplus
Benzoylaminoacetic acid KEGG COMPOUND
Benzoylaminoessigsäure ChemIDplus
Hippurate KEGG COMPOUND
Hippuric acid KEGG COMPOUND
Hippursäure ChemIDplus
N-benzoylglycine ChEBI
N-Benzoylglycine KEGG COMPOUND
Phenylcarbonylaminoacetic acid ChemIDplus
Manual Xrefs Databases
C00030483 KNApSAcK
C01586 KEGG COMPOUND
CPD-425 MetaCyc
Hippuric_acid Wikipedia
HMDB0000714 HMDB
View more database links
Registry Numbers Types Sources
1073987 Reaxys Registry Number Reaxys
495-69-2 CAS Registry Number KEGG COMPOUND
495-69-2 CAS Registry Number NIST Chemistry WebBook
495-69-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
04 October 2016