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3-Keto-L-gulonate 6-phosphate (M2MDB001113)

Record Information
Version2.0
Creation Date2012-05-31 14:36:25 -0600
Update Date2015-09-17 15:41:58 -0600
Secondary Accession Numbers
  • ECMDB20271
Identification
Name:3-Keto-L-gulonate 6-phosphate
Description3-keto-L-gulonate 6-phosphate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-Dehydro-L-gulonate-6-phosphate
  • 3-dehydro-L-Gulonic acid-6-phosphoric acid
  • 3-Keto-L-gulonate 6-P
  • 3-Keto-L-gulonate-6-phosphate
  • 3-Keto-L-gulonic acid 6-P
  • 3-Keto-L-gulonic acid 6-phosphate
  • 3-keto-L-Gulonic acid 6-phosphoric acid
  • 3-keto-L-Gulonic acid-6-phosphoric acid
Chemical Formula:C6H9O10P
Weight:Average: 272.103
Monoisotopic: 271.994430648
InChI Key:BDUIIKXSXFDPEC-UHFFFAOYSA-L
InChI:InChI=1S/C6H11O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-3,5,7-8,10H,1H2,(H,11,12)(H2,13,14,15)/p-2
CAS number:Not Available
IUPAC Name:2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid
Traditional IUPAC Name:2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid
SMILES:OC(COP([O-])([O-])=O)C(O)C(=O)C(O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Medium-chain keto acid
  • Beta-keto acid
  • Monoalkyl phosphate
  • Acyloin
  • Alpha-hydroxy acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Keto acid
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility16.4 g/LALOGPS
logP-2.1ALOGPS
logP-2.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area181.82 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability20.86 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-ascorbate 6-phosphate + Water + L-Ascorbate 6-phosphate > 3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate
3-Dehydro-L-gulonate + Adenosine triphosphate > 3-keto-L-gulonate 6-phosphate + Adenosine diphosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate + ADP
3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > Xylulose 5-phosphate + Carbon dioxide + Xylulose 5-phosphate
3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + Carbon dioxide + L-Xylulose 5-phosphate
3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + L-Xylulose 5-phosphate
SMPDB Pathways:
Ascorbate metabolismPW000793 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • L-ascorbate degradation I (bacterial, anaerobic) PWY0-301
  • L-ascorbate degradation II (bacterial, aerobic) PWY-6961
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2690000000-f449fb1ab1b0ad581c58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6v-6920000000-564500c3114af11aacc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-6b05c022383e0736c0f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fi0-8920000000-4ee0d90515ba8a6ee947View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-c74e1e3fbf6cd7457258View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7c6c3d1f837e7e96f4d7View in MoNA
References
References:
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID393
Kegg IDNot Available
ChemSpider ID384
Wikipedia IDNot Available
BioCyc IDCPD-2343
EcoCyc IDCPD-2343

Enzymes

Protein Details
1. L-xylulose/3-keto-L-gulonate kinase
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Catalyzes the phosphorylation of L-xylulose and 3-keto- L-gulonate. Is involved in L-lyxose utilization via xylulose, and may also be involved in the utilization of 2,3-diketo-L-gulonate
Gene Name:
lyx
Uniprot ID:
P37677
Molecular weight:
55155
Reactions
ATP + L-xylulose = ADP + L-xylulose 5-phosphate.
ATP + 3-dehydro-L-gulonate = ADP + 3-dehydro-L-gulonate 6-phosphate.
Protein Details
2. 3-keto-L-gulonate-6-phosphate decarboxylase sgbH
General function:
Involved in catalytic activity
Specific function:
Catalyzes the decarboxylation of 3-keto-L-gulonate-6-P into L-xylulose-5-P. May be involved in the utilization of 2,3- diketo-L-gulonate
Gene Name:
sgbH
Uniprot ID:
P37678
Molecular weight:
23445
Reactions
3-dehydro-L-gulonate 6-phosphate = L-xylulose 5-phosphate + CO(2).
Protein Details
3. 3-keto-L-gulonate-6-phosphate decarboxylase ulaD
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the decarboxylation of 3-keto-L-gulonate-6-P into L-xylulose-5-P. Is involved in the anaerobic L-ascorbate utilization
Gene Name:
ulaD
Uniprot ID:
P39304
Molecular weight:
23578
Reactions
3-dehydro-L-gulonate 6-phosphate = L-xylulose 5-phosphate + CO(2).
Protein Details
4. Probable L-ascorbate-6-phosphate lactonase ulaG
General function:
Involved in hydrolase activity
Specific function:
Probably catalyzes the hydrolysis of L-ascorbate-6-P into 3-keto-L-gulonate-6-P. Is essential for L-ascorbate utilization under anaerobic conditions. Also shows phosphodiesterase activity, hydrolyzing phosphodiester bond in the artificial chromogenic substrate bis-p-nitrophenyl phosphate (bis- pNPP)
Gene Name:
ulaG
Uniprot ID:
P39300
Molecular weight:
40060
Reactions
L-ascorbate 6-phosphate + H(2)O = 3-dehydro-L-gulonate 6-phosphate.