ECMDB: 2-Keto-3-deoxy-6-phosphogluconic acid (ECMDB01376) (M2MDB000363)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (594)

Record Information

Version

2.0

Creation Date

2012-05-31 13:51:17 -0600

Update Date

2015-06-03 15:54:04 -0600

Secondary Accession Numbers

ECMDB01376

Identification

Name:

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

Description

2-Keto-3-deoxy-6-phosphogluconic acid is a substrate for Fructose-bisphosphate aldolase A.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Dehydro-3-deoxy-6-phospho-D-gluconate
2-Dehydro-3-deoxy-6-phospho-D-gluconic acid
2-dehydro-3-Deoxy-D-gluconate 6-phosphate
2-Dehydro-3-deoxy-D-gluconate-6-phosphate
2-dehydro-3-Deoxy-D-gluconic acid-6-phosphoric acid
2-Keto-3-deoxy-6-P-gluconate
2-Keto-3-deoxy-6-P-gluconic acid
2-Keto-3-deoxy-6-phospho-D-gluconate
2-Keto-3-deoxy-6-phospho-D-gluconic acid
2-Keto-3-deoxy-6-phospho-Gluconate
2-Keto-3-deoxy-6-phospho-Gluconic acid
2-Keto-3-deoxy-6-phosphogluconate
2-Keto-3-deoxy-6-phosphogluconic acid
2-Keto-3-deoxygluconate-6-P
2-keto-3-Deoxygluconic acid-6-P
3-deoxy-D-erythro-hex-2-ulosonate-6-phosphate
3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate
3-Deoxy-D-erythro-hex-2-ulosonate 6-phosphate
3-Deoxy-D-erythro-hex-2-ulosonate-6-phosphate
3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate
3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphoric acid
3-Deoxy-D-erythro-hex-2-ulosonic acid-6-phosphoric acid
6-p-2-k-3-Deo-gluconate
6-p-2-k-3-Deo-gluconic acid
6-Phospho-2-dehydro-3-deoxy-D-gluconate
6-Phospho-2-dehydro-3-deoxy-D-gluconic acid
6-Phospho-2-dehydro-3-deoxygluconate
6-Phospho-2-dehydro-3-deoxygluconic acid
6-Phospho-2-keto-3-deoxygluconate
6-Phospho-2-keto-3-deoxygluconic acid
KDPGlcA

Chemical Formula:

C₆H₁₁O₉P

Weight:

Average: 258.1199
Monoisotopic: 258.014068462

InChI Key:

OVPRPPOVAXRCED-WVZVXSGGSA-N

InChI:

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

CAS number:

27244-54-8

IUPAC Name:

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

Traditional IUPAC Name:

kdpg intermediate

SMILES:

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

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 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

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	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:

SMPDB Pathways:

hexuronide and hexuronate degradation	PW000834
ketogluconate metabolism	PW002003

KEGG Pathways:

Arginine and proline metabolism ec00330
Glyoxylate and dicarboxylate metabolism ec00630
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Pentose and glucuronate interconversions ec00040
Pentose phosphate pathway ec00030

EcoCyc Pathways:

β-D-glucuronide and D-glucuronate degradation GLUCUROCAT-PWY
D-galacturonate degradation I GALACTUROCAT-PWY
Entner-Doudoroff pathway I ENTNER-DOUDOROFF-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9310000000-b977edea41f10c14441f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-01bc-6921400000-ca4d77ba878e92aaedf5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-1490000000-ea0f4bddcb2b9a63fa4f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01vy-6940000000-6658b367949c0aff033c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0076-9700000000-5dfc9ad3d3a20de41780	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a70-8290000000-46b63c8be3e78b565ecd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-969c103f10917fe5078a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-6b6797b8569981c766a4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06r7-6590000000-4bfcef169935d1cae20e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9200000000-17589b3b796f6001e623	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9000000000-cd26445e4e826ec3239a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9040000000-51b487070c5625d5eab9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-5c6f9eb036b780095d5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d484c197bb695cc95948	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15925
HMDB ID	HMDB01376
Pubchem Compound ID	3080745
Kegg ID	C04442
ChemSpider ID	2338483
Wikipedia ID	Not Available
BioCyc ID	2-KETO-3-DEOXY-6-P-GLUCONATE
EcoCyc ID	2-KETO-3-DEOXY-6-P-GLUCONATE

Enzymes

Protein Details

1. KHG/KDPG aldolase

General function:: Involved in catalytic activity
Specific function:: 4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate
Gene Name:: eda
Uniprot ID:: P0A955
Molecular weight:: 22284

Reactions

4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate.
2-dehydro-3-deoxy-D-gluconate 6-phosphate = pyruvate + D-glyceraldehyde 3-phosphate.

Protein Details

2. Phosphogluconate dehydratase

General function:: Involved in phosphogluconate dehydratase activity
Specific function:: 6-phospho-D-gluconate = 2-dehydro-3-deoxy-6- phospho-D-gluconate + H(2)O
Gene Name:: edd
Uniprot ID:: P0ADF6
Molecular weight:: 64639

Reactions

6-phospho-D-gluconate = 2-dehydro-3-deoxy-6-phospho-D-gluconate + H(2)O.

Protein Details

3. 2-dehydro-3-deoxygluconokinase

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6- phospho-2-dehydro-3-deoxy-D-gluconate
Gene Name:: kdgK
Uniprot ID:: P37647
Molecular weight:: 33962

Reactions

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6-phospho-2-dehydro-3-deoxy-D-gluconate.

2-Keto-3-deoxy-6-phosphogluconic acid (ECMDB01376) (M2MDB000363)

Structure for #<Compound:0xa7c6986c>

Enzymes

Reactions

Reactions

Reactions