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Record Information
Version1.0
Created at2006-02-23 11:12:23 UTC
Updated at2021-10-07 20:38:42 UTC
NP-MRD IDNP0001297
Secondary Accession NumbersNone
Natural Product 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
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 Mass194.1873 Da
Monoisotopic Mass194.06914 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Species Where Detected
    Species NameSourceReference
    Homo sapiens (Urine)KNApSAcK Database
    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
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point198.5 °CNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility13 mg/mLNot Available
    LogP-0.89C Fleck, H Bräunlich (1990) Arzneimittelforschung Aug;40(8):942-6. Factors determining the relationship between renal and hepatic excretion of xenobiotics (PMID: 2242089)
    Predicted Properties
    PropertyValueSource
    Water Solubility3.13 g/LALOGPS
    logP10(0) g/LALOGPS
    logP10(-1) g/LChemAxon
    logS10(-1.8) g/LALOGPS
    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
    HMDB IDHMDB0001867
    DrugBank IDDB00345
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022720
    KNApSAcK IDC00052153
    Chemspider ID2063
    KEGG Compound IDD06890
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkAminohippuric_Acid
    METLIN ID6359
    PubChem Compound2148
    PDB IDNot Available
    ChEBI ID104011
    Good Scents IDNot Available
    References
    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 ]