ChemFOnt: Showing chemical card for 2-Keto-3-deoxy-D-gluconic acid (CFc000001044)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:35 UTC

Chemfont ID

CFc000001044

Molecule Identification

Common Name

2-Keto-3-deoxy-D-gluconic acid

Definition

2-Keto-3-deoxy-D-gluconic acid is a substrate for Fructose-bisphosphate aldolase A.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Dehydro-3-deoxy-D-galactonate	ChEBI
2-Dehydro-3-deoxy-D-galactonic acid	Generator
2-Keto-3-deoxy-D-gluconate	Generator
2-oxo-3-Deoxygalactonic acid	MeSH, HMDB
3-Deoxy-D-threo-hexulosonic acid	MeSH, HMDB

Chemical Formula

C₆H₁₀O₆

Average Molecular Weight

178.14

Monoisotopic Molecular Weight

178.047738052

IUPAC Name

(4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid

Traditional Name

(4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid

CAS Registry Number

17510-99-5

SMILES

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

InChI Identifier

InChI=1S/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/t3-,5-/m1/s1

InChI Key

WPAMZTWLKIDIOP-NQXXGFSBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Alpha-keto acid
Beta-hydroxy ketone
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoaldonic acid (CHEBI:17028 )
hexonic acid (CHEBI:17028 )

Functional Ontology

Not Available

Feces (PMID: 29808030)

Cellular substructure

Cytoplasm (HMDB: HMDB0001353)

Source

Endogenous

Endogenous (HMDB: HMDB0001353)

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

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Inner Membrane Transport (PathBank: SMP0121270)
Hexuronide and Hexuronate Degradation (PathBank: SMP0000854)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	134 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.8	ChemAxon
logS	-0.12	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.32 m³·mol⁻¹	ChemAxon
Polarizability	15.54 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

External Links

HMDB ID

HMDB0001353

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022572

KNApSAcK ID

Not Available

Chemspider ID

168361

KEGG Compound ID

C01216

BioCyc ID

2-DEHYDRO-3-DEOXY-D-GLUCONATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6184

PubChem Compound

194024

PDB ID

Not Available

ChEBI ID

17028

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Plantier-Royon, Richard; Anker, Daniel; Robert-Baudouy, , Janine. New synthesis of 3-deoxy-D-erythro-2-hexulosonic acid (KDG) from D-glucose. Journal of Carbohydrate Chemistry (1991), 10(2), 239-49.

Showing chemical card for 2-Keto-3-deoxy-D-gluconic acid (CFc000001044)

MOL for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

3D MOL for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

3D SDF for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

3D-SDF for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

PDB for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

3D PDB for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

SMILES for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

INCHI for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

Structure for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)

3D Structure for CFc000001044 (2-Keto-3-deoxy-D-gluconic acid)