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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-23 11:12:23 UTC
Update Date2020-02-26 21:23:33 UTC
HMDB IDHMDB0001867
Secondary Accession Numbers
  • HMDB01867
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
Data?1582752213
Synonyms
ValueSource
Aminohippuric acidChEBI
N-(p-Aminobenzoyl)aminoacetic acidChEBI
N-(p-Aminobenzoyl)glycineChEBI
N-(Para-aminobenzoyl)glycineChEBI
p-AminohippurateChEBI
PAHChEBI
PahaChEBI
Para-aminohippuric acidChEBI
Paraaminohippuric acidChEBI
p-Aminohippuric acidKegg
AminohippateGenerator
Aminohippic acidGenerator
N-(p-Aminobenzoyl)aminoacetateGenerator
Para-aminohippateGenerator
Para-aminohippic acidGenerator
ParaaminohippateGenerator
Paraaminohippic acidGenerator
p-AminohippateGenerator
p-Aminohippic acidGenerator
4-AminohippateGenerator
4-Aminohippic acidGenerator
4-AminohippurateHMDB
AminohippurateHMDB
ChlorphentermineHMDB
N-(4-Aminobenzoyl)glycineHMDB
NefrotestHMDB
Para-aminohippurateHMDB
Aminohippurate sodiumHMDB
Sodium para-aminohippurateHMDB
Sodium, aminohippurateHMDB
p AminohippurateHMDB
Para-aminohippurate, sodiumHMDB
Para aminohippuric acidHMDB
4 Aminohippuric acidHMDB
NephrotestHMDB
Sodium para aminohippurateHMDB
p Aminohippuric acidHMDB
4-Aminohippuric acidChEBI
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 KeyHSMNQINEKMPTIC-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzoyl
  • Aniline or substituted anilines
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.82 m³·mol⁻¹ChemAxon
Polarizability19.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0910000000-d6e2bf0631a469ca607bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-3900000000-454a970609f4250f1022Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0910000000-d6e2bf0631a469ca607bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2900000000-13545b50126e3469611dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-5930000000-96c158cb0933998c6b3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f77-2900000000-a8b8a25d88057ce84dd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-010a61221aacb1a4cd70Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02fx-9200000000-507831f6ef0e0b10b17aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0900000000-886d3df0d88886b514f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-1900000000-017f11bcb65dee99bf7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9400000000-7ee96554ee69d820a99cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-fea9a305d118ff5d8f9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-4180dbe6449997335b79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-6c147308d50977004a22Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Pancreas
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified18.0 (5.0-283.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 References
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB00345
Phenol Explorer Compound IDNot Available
FooDB IDFDB022720
KNApSAcK IDNot Available
Chemspider ID2063
KEGG Compound IDD06890
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminohippuric_Acid
METLIN ID6359
PubChem Compound2148
PDB IDNot Available
ChEBI ID104011
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9679046 ]
  7. Daniel SS, James LS, Strauss J: Response to rapid volume expansion during the postnatal period. Pediatrics. 1981 Dec;68(6):809-13. [PubMed:7198775 ]
  8. Strauss J, Daniel SS, James LS: Postnatal adjustment in renal function. Pediatrics. 1981 Dec;68(6):802-8. [PubMed: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. [PubMed:7924159 ]
  10. Burckhardt G, Bahn A, Wolff NA: Molecular physiology of renal p-aminohippurate secretion. News Physiol Sci. 2001 Jun;16:114-8. [PubMed: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. [PubMed: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