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Showing Compound 4-Aminohippuric acid (FDB022720)

Record Information
Version1.0
Creation date2011-09-21 00:18:26 UTC
Update date2015-10-09 22:31:08 UTC
Primary IDFDB022720
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number61-78-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Chemical FormulaC9H10N2O3
IUPAC name2-[(4-aminophenyl)formamido]acetic acid
InChI IdentifierInChI=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
Isomeric SMILESNC1=CC=C(C=C1)C(=O)NCC(O)=O
Average Molecular Weight194.1873
Monoisotopic Molecular Weight194.069142196
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS4-Aminohippuric acid, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-d6e2bf0631a469ca607bSpectrum
GC-MS4-Aminohippuric acid, non-derivatized, GC-MS Spectrumsplash10-00di-3900000000-454a970609f4250f1022Spectrum
GC-MS4-Aminohippuric acid, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-d6e2bf0631a469ca607bSpectrum
Predicted GC-MS4-Aminohippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2900000000-13545b50126e3469611dSpectrum
Predicted GC-MS4-Aminohippuric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-5930000000-96c158cb0933998c6b3eSpectrum
Predicted GC-MS4-Aminohippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Aminohippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f77-2900000000-a8b8a25d88057ce84dd42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-010a61221aacb1a4cd702012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02fx-9200000000-507831f6ef0e0b10b17a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-5507cabf47dd4ffa240e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-9100000000-c8d97f1cc97cffcbe56f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-395b484545b8358e99372021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-fe5d8f1224f0bd9ade272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-9000000000-ccbc2ae9fc7edc68395f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-00di-0900000000-bcd0e15e018677f4d5ce2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-3900000000-53a86daaf93d39923f6c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-00di-0900000000-50659a062cb251ecd11d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-006x-9600000000-b0f0d35bf4f1f7ac6cab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-3af1801b411555af00c82021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0900000000-886d3df0d88886b514f52017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-1900000000-017f11bcb65dee99bf7e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9400000000-7ee96554ee69d820a99c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-fea9a305d118ff5d8f9f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-4180dbe6449997335b792017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-6c147308d50977004a222017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-c1f1f8223fde58be726f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-e900ce261e7b036f230a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9100000000-575f1135c946d98028842021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-2900000000-30ea092962a8f3debe622021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-11054566f6cbc98039dd2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-eef4c1f804c025cbb9782021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID2063
ChEMBL IDCHEMBL463
KEGG Compound IDD06890
Pubchem Compound ID2148
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00345
HMDB IDHMDB01867
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChlorphentermine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference