Showing metabocard for 4-Aminohippuric acid (BMDB0001867)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:24 UTC
Update Date2020-05-11 20:34:27 UTC
BMDB IDBMDB0001867
Secondary Accession Numbers
  • BMDB01867
Metabolite Identification
Common Name4-Aminohippuric acid
Description4-Aminohippuric acid, also known as para-aminohippate or PAH, 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. 4-Aminohippuric acid is a drug which is used to measure effective renal plasma flow (erpf) and to determine the functional capacity of the tubular excretory mechanism. 4-Aminohippuric acid is a strong basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Kidney
  • Pancreas
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001867
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
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)Not Available
General ReferencesNot Available