ChemFOnt: Showing chemical card for Diketogulonic acid (CFc000002608)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:32 UTC

Chemfont ID

CFc000002608

Molecule Identification

Common Name

Diketogulonic acid

Definition

Diketogulonic acid (DKG) is a metabolite of the degradation of vitamin C, the nonenzymatic hydrolysis-product of dehydroascorbate. Dehydroascorbate can be reduced back to ascorbate or hydrolyzed to DKG; the latter reaction is irreversible and DKG is devoid of antiscorbutic activity. The degradation pathway of vitamin C continues to produce l-erythrulose and oxalate as final products. DKG appears in human urine and represents approximately 20% of the vitamin C by-products (oxalate being approximately 44% and dehydroascorbate 20%). A major catabolic event in man is the cleavage of the molecule (presumably a spontaneous cleavage of DKG) between C2 and C3, with little if any decarboxylation. The oxalate formed in this way may contribute to the formation of kidney stones in susceptible individuals. However, the association between ascorbate supplementation and increased risk of kidney stone formation remains a matter of controversy. (PMID: 16698813 , 17222174 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoic acid	ChEBI
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoate	ChEBI
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acid	ChEBI
2,3-Diketo-L-gulonate	ChEBI
2,3-Diketo-L-gulonic acid	ChEBI
2,3-Dioxo-2,3-dideoxy-L-gulonic acid	ChEBI
2,3-L-Diketogulonic acid	ChEBI
Diketo-L-gulonic acid	ChEBI
L-Threo-(2,3)-hexodiulosonsaeure	ChEBI
L-Threo-2,3-hexodiurosonic acid	ChEBI
Threo-2,3-hexodiulosonic acid	ChEBI
(4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoate	Generator
2,3-Dioxo-2,3-dideoxy-L-gulonate	Generator
2,3-L-Diketogulonate	Generator
Diketo-L-gulonate	Generator
L-Threo-2,3-hexodiurosonate	Generator
Threo-2,3-hexodiulosonate	Generator
Diketogulonate	Generator
2,3-Diketogulonic acid	HMDB
2,3-Dioxo-D-gulonate	HMDB
L-Threo-2,3-hexodiulosonic acid	HMDB
L-Threo-hexo-2,3-diulosonic acid	HMDB
Acid, 2,3-diketogulonic	HMDB
2,3 Diketogulonic acid	HMDB
Diketo-gulonate	HMDB
2,3-Diketogulonate	HMDB

Chemical Formula

C₆H₈O₇

Average Molecular Weight

192.1235

Monoisotopic Molecular Weight

192.02700261

IUPAC Name

(4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid

Traditional Name

diketogulonic acid

CAS Registry Number

3409-57-2

SMILES

OC[C@H](O)[C@@H](O)C(=O)C(=O)C(O)=O

InChI Identifier

InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3+/m0/s1

InChI Key

GJQWCDSAOUMKSE-STHAYSLISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Hexose monosaccharide
Medium-chain keto acid
Beta-keto acid
Sugar acid
Acyloin
Alpha-keto acid
Alpha-diketone
Beta-hydroxy ketone
Keto acid
Monosaccharide
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:15622 )
dioxo monocarboxylic acid (CHEBI:15622 )
alpha-diketone (CHEBI:15622 )
carbohydrate acid (CHEBI:15622 )
Oxo fatty acids (LMFA01060195 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0005971)

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	59.9 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.6	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.04 m³·mol⁻¹	ChemAxon
Polarizability	15.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon