ChemFOnt: Showing chemical card for Quinolacetic acid (CFc000220521)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:40 UTC

Chemfont ID

CFc000220521

Molecule Identification

Common Name

Quinolacetic acid

Definition

Quinolacetic acid is a by-product of the partially defective enzyme, 4-hydroxyphenylpyruvate dioxygenase (PMID: 6619234 ). When present in sufficiently high levels, quinolacetic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of quinolacetic acid are associated with hawkinsinuria (PMID: 6619234 ). Hawkinsinuria is characterized by the inability to break down the amino acid tyrosine. The features of this condition usually appear around the time infants are weaned off breast milk and begin to use formula. The signs and symptoms may include the following: failure to gain weight and grow at the expected rate (failure to thrive), abnormally high acid levels in the blood (acidosis), and fine or sparse hair. Hawkinsin is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated hawkinsinuria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Quinolacetate	Generator

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.148

Monoisotopic Molecular Weight

168.042258738

IUPAC Name

2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid

Traditional Name

(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid

CAS Registry Number

55604-87-0

SMILES

OC(=O)CC1(O)C=CC(=O)C=C1

InChI Identifier

InChI=1S/C8H8O4/c9-6-1-3-8(12,4-2-6)5-7(10)11/h1-4,12H,5H2,(H,10,11)

InChI Key

RFJUCKOEXRTZPN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0240257)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	36.7 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	0.048	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.47 m³·mol⁻¹	ChemAxon
Polarizability	15.02 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

HMDB0240257

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4955602

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quinolacetic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Quinolacetic acid (CFc000220521)

MOL for CFc000220521 (Quinolacetic acid)

3D MOL for CFc000220521 (Quinolacetic acid)

3D SDF for CFc000220521 (Quinolacetic acid)

3D-SDF for CFc000220521 (Quinolacetic acid)

PDB for CFc000220521 (Quinolacetic acid)

3D PDB for CFc000220521 (Quinolacetic acid)

SMILES for CFc000220521 (Quinolacetic acid)

INCHI for CFc000220521 (Quinolacetic acid)

Structure for CFc000220521 (Quinolacetic acid)

3D Structure for CFc000220521 (Quinolacetic acid)