P. aeruginosa Metabolome Database: 2,5-Diketo-D-gluconate (PAMDB000592)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000592

Identification

Name:

2,5-Diketo-D-gluconate

Description:

2,5-Diketo-D-gluconate is an intermediate in the synthesis of ascorbic acid. It is a substrate for the enzyme 2,5-diketo-D-gluconic acid reductase B. This enzyme catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG) with the following reaction: 2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2,5-Didehydro-D-gluconate
2,5-Didehydro-D-gluconic acid
2,5-diketo-D-gluconate
2,5-Diketo-D-gluconic acid
2,5-Diketogluconate
2,5-Diketogluconic acid
2-Dehydro-L-idonate
2-Dehydro-L-idonic acid
D-Threo-hexo-2,5-diulosonate
D-Threo-hexo-2,5-diulosonic acid

Chemical Formula:

C₆H₇O₇

Average Molecular Weight:

191.1156

Monoisotopic Molecular Weight:

191.019177578

InChI Key:

RXMWXENJQAINCC-DMTCNVIQSA-M

InChI:

InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h3-4,7,9-10H,1H2,(H,12,13)/p-1/t3-,4+/m1/s1

CAS number:

53736-12-2

IUPAC Name:

(3S,4S)-3,4,6-trihydroxy-2,5-dioxohexanoate

Traditional IUPAC Name:

2,5-diketo-D-gluconate

SMILES:

[H][C@@](O)(C(=O)CO)[C@]([H])(O)C(=O)C([O-])=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Hydroxy fatty acid
Medium-chain keto acid
Beta-hydroxy acid
Monosaccharide
Keto acid
Hydroxy acid
Beta-hydroxy ketone
Beta-ketoaldehyde
Alpha-keto acid
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Polyol
Ketone
Carboxylic acid salt
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid anion (CHEBI:11449 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	173.0 mg/mL	ALOGPS
logP	-1.1	ALOGPS
logP	-2	ChemAxon
logS	-0.08	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	134.96 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.65 m³·mol^-1	ChemAxon
Polarizability	15.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

2,5-Diketo-D-gluconate + Hydrogen ion + NADPH >2 -Dehydro-L-gulonate + NADP
2,5-Diketo-D-gluconate + Hydrogen ion + NADH > 5-Keto-D-gluconate + NAD
2,5-Diketo-D-gluconate + Hydrogen ion + NADPH > 5-Keto-D-gluconate + NADP
Hydrogen ion + NADPH + 2,5-Diketo-D-gluconate <> 2-Dehydro-D-gluconate + NADP
2,5-Diketo-D-gluconate + NAD(P)H + Hydrogen ion > 2-keto-L-gulonate + NAD(P)<sup>+</sup>
NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-66697df72cf11dbf7f41	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ec-7900000000-97ebe6ed711475246178	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9200000000-a963788665da60d07e0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00ko-7900000000-eb51687ff97b29540276	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9400000000-5a948ab5e28d4d5a185b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-60c5fc89ff115a2f2c2d	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	11449
HMDB ID	Not Available
Pubchem Compound ID	9548631
Kegg ID	C02780
ChemSpider ID	7827554
Wikipedia ID	Not Available
BioCyc ID	25-DIDEHYDRO-D-GLUCONATE
EcoCyc ID	25-DIDEHYDRO-D-GLUCONATE

2,5-Diketo-D-gluconate (PAMDB000592)

Structure for 2,5-Diketo-D-gluconate (PAMDB000592)