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Record Information
Version	2.0
Creation Date	2012-05-31 14:25:45 -0600
Update Date	2015-06-03 17:19:14 -0600
Secondary Accession Numbers	ECMDB20067
Identification
Name:	3-Dehydro-L-gulonate 6-phosphate
Description	3-dehydro-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab25a9d0> Close
Synonyms:	3-Dehydro-L-gulonate 6-phosphate 3-Dehydro-L-gulonate-6-phosphate 3-Dehydro-L-gulonic acid 6-phosphate 3-dehydro-L-Gulonic acid 6-phosphoric acid 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-phosphoric acid 6-O-Phosphono-L-xylo-hex-3-ulosonate 6-O-Phosphono-L-xylo-hex-3-ulosonic acid L-Xylo-hex-3-ulosonate 6-(dihydrogen phosphate) L-Xylo-hex-3-ulosonic acid 6-(dihydrogen phosphate) L-xylo-Hex-3-ulosonic acid 6-(dihydrogen phosphoric acid)
Chemical Formula:	C6H11O10P
Weight:	Average: 274.1193 Monoisotopic: 274.008983084
InChI Key:	BDUIIKXSXFDPEC-LWKDLAHASA-N
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)/t2-,3+,5-/m0/s1
CAS number:	Not Available
IUPAC Name:	(2S,4R,5S)-2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid
Traditional IUPAC Name:	(2S,4R,5S)-2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid
SMILES:	[H][C@](O)(COP(O)(O)=O)[C@@]([H])(O)C(=O)[C@]([H])(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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Pentose phosphates
Alternative Parents	Hexoses Monosaccharide phosphates Medium-chain keto acids and derivatives Beta-keto acids and derivatives Monoalkyl phosphates 1,3-dicarbonyl compounds Acyloins Alpha hydroxy acids and derivatives Beta-hydroxy ketones Alpha-hydroxy ketones Secondary alcohols Carboxylic acids Polyols Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides
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 Framework	Aliphatic acyclic compounds
External Descriptors	ketoaldonic acid derivative (CHEBI:49039 )
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 16.4 g/L ALOGPS logP -2.1 ALOGPS logP -2.8 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 1.47 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 181.82 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 48.45 m³·mol⁻¹ ChemAxon Polarizability 20.67 ų 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:	3-Dehydro-L-gulonate 6-phosphate + Hydrogen ion <> Carbon dioxide + L-Xylulose 5-phosphate 3-Dehydro-L-gulonate + Adenosine triphosphate > 3-Dehydro-L-gulonate 6-phosphate + ADP + Hydrogen ion L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate + Hydrogen ion 3-Dehydro-L-gulonate + Adenosine triphosphate <> 3-Dehydro-L-gulonate 6-phosphate + ADP L-Ascorbate 6-phosphate + Water <> 3-Dehydro-L-gulonate 6-phosphate L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate Hydrogen ion + 3-Dehydro-L-gulonate 6-phosphate > L-Xylulose 5-phosphate + Carbon dioxide Adenosine triphosphate + 3-Dehydro-L-gulonate > ADP + 3-Dehydro-L-gulonate 6-phosphate 3-Dehydro-L-gulonate 6-phosphate > L-Xylulose 5-phosphate + Carbon dioxide
SMPDB Pathways:	Not Available
KEGG Pathways:	Ascorbate and aldarate metabolism ec00053 Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120 Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:	L-ascorbate degradation I (bacterial, anaerobic) PWY0-301 L-ascorbate degradation II (bacterial, aerobic) PWY-6961
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_4_15) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-056r-2690000000-f449fb1ab1b0ad581c58 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a6v-6920000000-564500c3114af11aacc1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a6r-9400000000-6b05c022383e0736c0f2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0fi0-8920000000-4ee0d90515ba8a6ee947 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9300000000-c74e1e3fbf6cd7457258 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-7c6c3d1f837e7e96f4d7 View in MoNA 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 1D NMR 1H 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 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 49039 HMDB ID Not Available Pubchem Compound ID 11954078 Kegg ID C14899 ChemSpider ID 10128373 Wikipedia ID Not Available BioCyc ID CPD-2343 EcoCyc ID CPD-2343

Enzymes