ChemFOnt: Showing chemical card for Alpha-Hydroxyhippuric acid (CFc000001622)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:17 UTC

Chemfont ID

CFc000001622

Molecule Identification

Common Name

Alpha-Hydroxyhippuric acid

Definition

Alpha-Hydroxyhippuric acid, also known as alpha-hydroxybenzoylglycine or a-hydroxyhippate, 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. Alpha-Hydroxyhippuric acid (or Benzamidohydroxyacetic acid) is a carboxylic acid occasionally present in human biofluids. Alpha-hydroxyhippuric acid should not be confused with 2-hydroxyhippuric acid. It is used in the formulation of some herbicides and inks to enhance their action (Patents US 1996-657134, US 1975-627965). It is a substrate for the enzyme peptidyl-alpha-hydroxyglycine alpha-amidating lyase. Alpha-Hydroxyhippuric acid (or Benzamidohydroxyacetic acid) is a hippuric acid derivative that is occasionally present in human biofluids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(Benzoylamino)-2-hydroxyacetic acid	ChEBI
2-Benzamidooxyacetic acid	ChEBI
alpha-Hydroxybenzoylglycine	ChEBI
2-(Benzoylamino)-2-hydroxyacetate	Generator
2-Benzamidooxyacetate	Generator
a-Hydroxybenzoylglycine	Generator
Α-hydroxybenzoylglycine	Generator
a-Hydroxyhippate	Generator
a-Hydroxyhippic acid	Generator
alpha-Hydroxyhippate	Generator
alpha-Hydroxyhippic acid	Generator
Α-hydroxyhippate	Generator
Α-hydroxyhippic acid	Generator
(benzoylamino)Hydroxyacetic acid	HMDB
a-Hydroxyhippuric acid	HMDB
Benzamidohydroxyacetic acid	HMDB
2-benzamido-2-hydroxyacetic acid	HMDB

Chemical Formula

C₉H₉NO₄

Average Molecular Weight

195.1721

Monoisotopic Molecular Weight

195.053157781

IUPAC Name

2-hydroxy-2-(phenylformamido)acetic acid

Traditional Name

α-hydroxybenzoylglycine

CAS Registry Number

16555-77-4

SMILES

OC(NC(=O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C9H9NO4/c11-7(10-8(12)9(13)14)6-4-2-1-3-5-6/h1-5,8,12H,(H,10,11)(H,13,14)

InChI Key

GCWCVCCEIQXUQU-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
Benzoyl
Alpha-hydroxy acid
Hydroxy acid
Carboxamide group
Secondary carboxylic acid amide
Alkanolamine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acyl-amino acid (CHEBI:68451 )

Functional Ontology

Not Available

Urine (PMID: 20853910)

Cellular substructure

Cytoplasm (HMDB: HMDB0002404)

Source

Endogenous

Endogenous (HMDB: HMDB0002404)

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)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.98 g/L	ALOGPS
logP	0.02	ALOGPS
logP	0.24	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.32 m³·mol⁻¹	ChemAxon
Polarizability	18.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002404

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022997

KNApSAcK ID

Not Available

Chemspider ID

396607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6667

PubChem Compound

450272

PDB ID

Not Available

ChEBI ID

68451

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Fukuoka, Masamichi; Kiyohara, Tuyoshi; Kobayashi, Tetsu; Kojima, Shuji; Tanaka, Akira; Kubodera, Akiko. Synthesis and preclinical evaluation of technetium-99m-labeled hippurate analogs. Nuclear Medicine and Biology (1995), 22(2), 181-91.

Showing chemical card for Alpha-Hydroxyhippuric acid (CFc000001622)

MOL for CFc000001622 (Alpha-Hydroxyhippuric acid)

3D MOL for CFc000001622 (Alpha-Hydroxyhippuric acid)

3D SDF for CFc000001622 (Alpha-Hydroxyhippuric acid)

3D-SDF for CFc000001622 (Alpha-Hydroxyhippuric acid)

PDB for CFc000001622 (Alpha-Hydroxyhippuric acid)

3D PDB for CFc000001622 (Alpha-Hydroxyhippuric acid)

SMILES for CFc000001622 (Alpha-Hydroxyhippuric acid)

INCHI for CFc000001622 (Alpha-Hydroxyhippuric acid)

Structure for CFc000001622 (Alpha-Hydroxyhippuric acid)

3D Structure for CFc000001622 (Alpha-Hydroxyhippuric acid)