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Record Information
Version3.6
Creation Date2006-02-23 11:12:23 UTC
Update Date2016-11-21 16:46:38 UTC
HMDB IDHMDB01867
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Aminohippuric acid
Description4-Aminohippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. 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. Renal proximal tubules secrete various organic anions, including drugs and p-aminohippurate (PAH). Uptake of PAH from blood into tubule cells occurs by exchange with intracellular alpha-ketoglutarate and is mediated by the organic anion transporter 1. PAH exit into tubule lumen is species specific and may involve ATP-independent and -dependent transporters. (PMID 11443229 ). Enhanced secretion of p-aminohippuric acid occurs in Fanconi's syndrome (FS). FS is associated with numerous varieties of inherited and acquired conditions; FS is characterized by a generalized transport defect in the proximal tubules, leading to renal losses of glucose, phosphate, calcium, uric acid, amino acids, bicarbonates, and other organic compounds. (PMID 12552490 ).
Structure
Thumb
Synonyms
ValueSource
4-Aminohippuric acidChEBI
N-(P-Aminobenzoyl)aminoacetic acidChEBI
N-(P-Aminobenzoyl)glycineChEBI
N-(Para-aminobenzoyl)glycineChEBI
P-AminohippurateChEBI
PAHChEBI
PahaChEBI
Para-aminohippuric acidChEBI
Paraaminohippuric acidChEBI
4-AminohippateGenerator
4-Aminohippic acidGenerator
AminohippateGenerator
Aminohippic acidGenerator
N-(P-Aminobenzoyl)aminoacetateGenerator
P-Aminohippuric acidGenerator
Para-aminohippateGenerator
Para-aminohippic acidGenerator
ParaaminohippateGenerator
Paraaminohippic acidGenerator
P-AminohippateGenerator
P-Aminohippic acidGenerator
4-AminohippurateHMDB
AminohippurateHMDB
ChlorphentermineHMDB
N-(4-Aminobenzoyl)glycineHMDB
NefrotestHMDB
Para-aminohippurateHMDB
Chemical FormulaC9H10N2O3
Average Molecular Weight194.1873
Monoisotopic Molecular Weight194.069142196
IUPAC Name2-[(4-aminophenyl)formamido]acetic acid
Traditional Nameaminohippurate
CAS Registry Number61-78-9
SMILES
NC1=CC=C(C=C1)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)
InChI KeyInChIKey=HSMNQINEKMPTIC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzamides
Direct ParentHippuric acids
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzoic acid or derivatives
  • Aminobenzamide
  • Substituted aniline
  • Benzoyl
  • Aniline
  • Primary aromatic amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point198.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13 mg/mLNot Available
LogP-0.89FLECK,C & BRAUNLICH,H (1990)
Predicted Properties
PropertyValueSource
Water Solubility3.13 mg/mLALOGPS
logP0ALOGPS
logP-1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.7ChemAxon
pKa (Strongest Basic)4.24ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.82 m3·mol-1ChemAxon
Polarizability19.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0006-0910000000-d6e2bf0631a469ca607bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f77-2900000000-a8b8a25d88057ce84dd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-010a61221aacb1a4cd70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02fx-9200000000-507831f6ef0e0b10b17aView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Pancreas
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified18.0 (5.0-283.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
UrineDetected and Quantified0.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.878 +/- 0.989 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.3 (1.0-7.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified2.328 +/- 0.508 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022720
KNApSAcK IDNot Available
Chemspider ID2063
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminohippuric_acid
NuGOwiki LinkHMDB01867
Metagene LinkHMDB01867
METLIN ID6359
PubChem Compound2148
PDB IDNot Available
ChEBI ID104011
References
Synthesis ReferenceBarnabei, Ottavio; Cocito, Carlo. Synthesis of p-aminohippuric acid in presence of thyroxine and a hepatic factor. Ricerca sci. (1955), 25 3329-32.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Giudice PL, Dubourg L, Hadj-Aissa A, Said MH, Claris O, Audra P, Martin X, Cochat P: Renal function of children exposed to cyclosporin in utero. Nephrol Dial Transplant. 2000 Oct;15(10):1575-9. [11007824 ]
  2. Devaux S, Gellert S, Streichan F: [A new method for the determination of the maximal tubular transport of p-aminohippuric acid without urine analysis in children with transplanted kidney] Z Urol Nephrol. 1984 Nov;77(11):639-46. [6395558 ]
  3. Gunston KD, Davey DD: The association between measured and clinically assessed amniotic fluid volume and fetal growth and nutrition. S Afr Med J. 1978 Sep 16;54(12):499-500. [734583 ]
  4. van Otterlo LC, Wladimiroff JW, Wallenburg HC: Relationship between fetal urine production and amniotic fluid volume in normal pregnancy and pregnancy complicated by diabetes. Br J Obstet Gynaecol. 1977 Mar;84(3):205-9. [843496 ]
  5. Malek RS, Wilkiemeyer RM, Boyce WH: The stone-forming kidney: a study of functional differences between individual kidneys in idiopathic renal lithiasis. J Urol. 1976 Jul;116(1):11-4. [933268 ]
  6. Stanley AJ, Forrest EH, Dabos K, Bouchier IA, Hayes PC: Natriuretic effect of an adenosine-1 receptor antagonist in cirrhotic patients with ascites. Gastroenterology. 1998 Aug;115(2):406-11. [9679046 ]
  7. Daniel SS, James LS, Strauss J: Response to rapid volume expansion during the postnatal period. Pediatrics. 1981 Dec;68(6):809-13. [7198775 ]
  8. Strauss J, Daniel SS, James LS: Postnatal adjustment in renal function. Pediatrics. 1981 Dec;68(6):802-8. [7198774 ]
  9. Edlund A, Ohlsen H, Sollevi A: Renal effects of local infusion of adenosine in man. Clin Sci (Lond). 1994 Aug;87(2):143-9. [7924159 ]
  10. Burckhardt G, Bahn A, Wolff NA: Molecular physiology of renal p-aminohippurate secretion. News Physiol Sci. 2001 Jun;16:114-8. [11443229 ]
  11. Izzedine H, Launay-Vacher V, Isnard-Bagnis C, Deray G: Drug-induced Fanconi's syndrome. Am J Kidney Dis. 2003 Feb;41(2):292-309. [12552490 ]

Enzymes

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
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
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
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