ChemFOnt: Showing chemical card for Benzoquinoneacetic acid (CFc000001569)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:13 UTC

Chemfont ID

CFc000001569

Molecule Identification

Common Name

Benzoquinoneacetic acid

Definition

Benzoquinoneacetic acid (BQA) is an oxidized form of homogentisic acid. The oxidation of homogentisic acid to BQA is catalyzed by the enzyme polyphenol oxidase. BQA is secreted in high quantities in the urine of patients suffering from cyanosis caused by vitamin C deficiency (Ella H. Fishberg, J. Biol. Chem., Jan 1948; 172: 155 - 163). Cyanosis is the bluish colouration of the skin due to the presence of deoxygenated hemoglobin in blood vessels near the skin surface. When present in sufficiently high levels, BQA can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of BQA are associated with alkaptonuria (OMIM: 203500 ), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of both homogentisic acid and BQA in the blood and tissues. When excreted in the urine, these compounds give it an unusually dark color. The accumulating BQA causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, BQA can form polymers that resemble the dark skin pigment melanin. These are deposited in collagen, especially in tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benzoquinoneacetate	Generator
BQA	HMDB
Benzoquinone acetic acid	HMDB
2-(3,6-Dioxocyclohexa-1,4-dien-1-yl)acetate	Generator, HMDB

Chemical Formula

C₈H₆O₄

Average Molecular Weight

166.1308

Monoisotopic Molecular Weight

166.02660868

IUPAC Name

2-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid

Traditional Name

benzoquinoneacetic acid

CAS Registry Number

10275-07-7

SMILES

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

InChI Identifier

InChI=1S/C8H6O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3H,4H2,(H,11,12)

InChI Key

RAPRJRLALQKSHB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0002334)

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

Indirect biological role

Metabotoxin

Osteotoxin (HMDB: HMDB0002334)

Renal toxin (HMDB: HMDB0002334)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.46 g/L	ALOGPS
logP	0.41	ALOGPS
logP	0.54	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-8.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.65 m³·mol⁻¹	ChemAxon
Polarizability	14.58 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

External Links

HMDB ID

HMDB0002334

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022966

KNApSAcK ID

Not Available

Chemspider ID

13628337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6628

PubChem Compound

21252288

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Benzoquinoneacetic acid (CFc000001569)

MOL for CFc000001569 (Benzoquinoneacetic acid)

3D MOL for CFc000001569 (Benzoquinoneacetic acid)

3D SDF for CFc000001569 (Benzoquinoneacetic acid)

3D-SDF for CFc000001569 (Benzoquinoneacetic acid)

PDB for CFc000001569 (Benzoquinoneacetic acid)

3D PDB for CFc000001569 (Benzoquinoneacetic acid)

SMILES for CFc000001569 (Benzoquinoneacetic acid)

INCHI for CFc000001569 (Benzoquinoneacetic acid)

Structure for CFc000001569 (Benzoquinoneacetic acid)

3D Structure for CFc000001569 (Benzoquinoneacetic acid)