ChemFOnt: Showing chemical card for 4-Aminohippuric acid (CFc000001241)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:50 UTC

Chemfont ID

CFc000001241

Molecule Identification

Common Name

4-Aminohippuric acid

Definition

4-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Aminohippuric acid	ChEBI
N-(p-Aminobenzoyl)aminoacetic acid	ChEBI
N-(p-Aminobenzoyl)glycine	ChEBI
N-(Para-aminobenzoyl)glycine	ChEBI
p-Aminohippurate	ChEBI
PAH	ChEBI
Paha	ChEBI
Para-aminohippuric acid	ChEBI
Paraaminohippuric acid	ChEBI
p-Aminohippuric acid	Kegg
Aminohippate	Generator
Aminohippic acid	Generator
N-(p-Aminobenzoyl)aminoacetate	Generator
Para-aminohippate	Generator
Para-aminohippic acid	Generator
Paraaminohippate	Generator
Paraaminohippic acid	Generator
p-Aminohippate	Generator
p-Aminohippic acid	Generator
4-Aminohippate	Generator
4-Aminohippic acid	Generator
4-Aminohippurate	HMDB
Aminohippurate	HMDB
Chlorphentermine	HMDB
N-(4-Aminobenzoyl)glycine	HMDB
Nefrotest	HMDB
Para-aminohippurate	HMDB
Aminohippurate sodium	HMDB
Sodium para-aminohippurate	HMDB
Sodium, aminohippurate	HMDB
p Aminohippurate	HMDB
Para-aminohippurate, sodium	HMDB
Para aminohippuric acid	HMDB
4 Aminohippuric acid	HMDB
Nephrotest	HMDB
Sodium para aminohippurate	HMDB
p Aminohippuric acid	HMDB
4-Aminohippuric acid	ChEBI

Chemical Formula

C₉H₁₀N₂O₃

Average Molecular Weight

194.1873

Monoisotopic Molecular Weight

194.069142196

IUPAC Name

2-[(4-aminophenyl)formamido]acetic acid

Traditional Name

aminohippurate

CAS Registry Number

61-78-9

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 Key

HSMNQINEKMPTIC-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:104011 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16169291)

Organ

Kidney (HMDB: HMDB0001867)
Pancreas (HMDB: HMDB0001867)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 25486321)

Cellular substructure

Cytoplasm (HMDB: HMDB0001867)

Source

Exogenous

Exogenous (HMDB: HMDB0001867)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001867)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001867)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.13 g/L	ALOGPS
logP	0	ALOGPS
logP	-1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.7	ChemAxon
pKa (Strongest Basic)	4.24	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.82 m³·mol⁻¹	ChemAxon
Polarizability	19.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon