ChemFOnt: Showing chemical card for 2-Keto-3-deoxy-6-phosphogluconic acid (CFc000001064)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:37 UTC

Chemfont ID

CFc000001064

Molecule Identification

Common Name

2-Keto-3-deoxy-6-phosphogluconic acid

Definition

2-Keto-3-deoxy-6-phosphogluconic acid is a substrate for Fructose-bisphosphate aldolase A. It can be found in Achromobacter, Alcaligenes, Clostridium and Rhodobacteraceae (PMID: 5383859 ; PMID: 5304016 ) (M. Szymona and M. Doudoroff. Carbohydrate Metabolism in Rhodopseudomonas spheroides. J. Gen. Microbiol (1960). 22: 167-183).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Dehydro-3-deoxy-6-phospho-D-gluconate	ChEBI
2-Dehydro-3-deoxy-D-gluconate 6-phosphate	ChEBI
2-Keto-3-deoxy-6-phosphogluconate	ChEBI
3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate	ChEBI
6-Phospho-2-dehydro-3-deoxy-D-gluconate	ChEBI
KDPG Intermediate	ChEBI
2-Dehydro-3-deoxy-6-phospho-D-gluconic acid	Generator
2-Dehydro-3-deoxy-D-gluconic acid 6-phosphoric acid	Generator
3-Deoxy-D-erythro-hex-2-ulosonate 6-phosphate	Generator
3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphoric acid	Generator
6-Phospho-2-dehydro-3-deoxy-D-gluconic acid	Generator
KDPG Intermediic acid	Generator
2-dehydro-3-Deoxy-D-gluconate-6-phosphate	HMDB
2-keto-3-Deoxy-6-P-gluconate	HMDB
2-keto-3-Deoxy-6-phospho-gluconate	HMDB
2-keto-3-Deoxygluconate-6-P	HMDB
6-P-2-K-3-deo-Gluconate	HMDB
6-phospho-2-dehydro-3-Deoxygluconate	HMDB
6-phospho-2-keto-3-Deoxygluconate	HMDB

Chemical Formula

C₆H₁₁O₉P

Average Molecular Weight

258.1199

Monoisotopic Molecular Weight

258.014068462

IUPAC Name

(4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acid

Traditional Name

kdpg intermediate

CAS Registry Number

27244-54-8

SMILES

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

InChI Identifier

InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1

InChI Key

OVPRPPOVAXRCED-WVZVXSGGSA-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
Monoalkyl phosphate
Alpha-keto acid
Beta-hydroxy ketone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Alpha-hydroxy ketone
Ketone
1,2-diol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoaldonic acid phosphate (CHEBI:15925 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0001376)

Microbe

Microbe (HMDB: HMDB0001376)
Clostridium (HMDB: HMDB0001376)
Achromobacter (HMDB: HMDB0001376)
Alcaligenes (HMDB: HMDB0001376)
Rlzodopseudomonas spheroides (HMDB: HMDB0001376)

Exogenous

Exogenous (HMDB: HMDB0001376)

Food

Animal origin

Poultry

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

Ketogluconate Metabolism (PathBank: SMP0122204)
Hexuronide and Hexuronate Degradation (PathBank: SMP0000854)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	14.3 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.9	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	47.19 m³·mol⁻¹	ChemAxon
Polarizability	20.17 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