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Record Information
Version	2.0
Creation Date	2012-05-31 14:08:05 -0600
Update Date	2015-06-03 15:54:51 -0600
Secondary Accession Numbers	ECMDB06334
Identification
Name:	3-Dehydro-L-gulonate
Description	3-Dehydro-L-gulonate is an intermediate in ascorbic acid degradation. It is a substrate for the enzyme 2,3-diketo-L-gulonate reductase. This enzyme catalyzes the reduction of 2,3-diketo-L-gulonate in the presence of NADH, to form 3-keto-L-gulonate. It participates in the reaction: 3-dehydro-L-gulonate + NAD(P)+ = (4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate + NAD(P)H. Several pathways for the irreversible catabolism of ascorbate have been described. Facultatively aerobic bacteria such as Escherichia coli degrade L-ascorbate by different pathways under aerobic and anaerobic conditions. The anaerobic pathway begins with phosphorylation of ascorbate (mediated by a PTS-type transporter), while the aerobic pathway proceeds via 2,3-dioxo-L-gulonate. Both pathways produce D-xylulose 5-phosphate, a centeral metabolite that is fed into the pentose phosphate pathway.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb1951c88> Close
Synonyms:	3-Dehydro-L-gulonate 3-Dehydro-L-gulonic acid L-Xylo-hex-3-ulosonate L-Xylo-hex-3-ulosonic acid
Chemical Formula:	C6H10O7
Weight:	Average: 194.1394 Monoisotopic: 194.042652674
InChI Key:	WTAHRPBPWHCMHW-LWKDLAHASA-N
InChI:	InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,5,7-9,11H,1H2,(H,12,13)/t2-,3+,5-/m0/s1
CAS number:	Not Available
IUPAC Name:	(2S,4R,5S)-2,4,5,6-tetrahydroxy-3-oxohexanoic acid
Traditional IUPAC Name:	3-dehydro-L-gulonic acid
SMILES:	OC[C@H](O)[C@@H](O)C(=O)[C@H](O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Sugar acids and derivatives
Alternative Parents	Hexoses Medium-chain keto acids and derivatives Beta-keto acids and derivatives Beta-hydroxy ketones Alpha hydroxy acids and derivatives Acyloins 1,3-dicarbonyl compounds Alpha-hydroxy ketones Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives
Substituents	Hexose monosaccharide Medium-chain keto acid Beta-keto acid Sugar acid Acyloin Alpha-hydroxy acid Beta-hydroxy ketone Hydroxy acid Keto acid 1,3-dicarbonyl compound Monosaccharide Alpha-hydroxy ketone Ketone Secondary alcohol Carboxylic acid Carboxylic acid derivative Monocarboxylic acid or derivatives Polyol Alcohol Hydrocarbon derivative Carbonyl group Organic oxide Primary alcohol Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	ketoaldonic acid (CHEBI:16142 ) hexonic acid (CHEBI:16142 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 105 g/L ALOGPS logP -2.6 ALOGPS logP -2.6 ChemAxon logS -0.27 ALOGPS pKa (Strongest Acidic) 3.16 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 135.29 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 37.58 m³·mol⁻¹ ChemAxon Polarizability 16.3 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:	2,3-Diketo-L-gulonate + Hydrogen ion + NADH > 3-Dehydro-L-gulonate + NAD 3-Dehydro-L-gulonate + Adenosine triphosphate > 3-Dehydro-L-gulonate 6-phosphate + ADP + Hydrogen ion 3-Dehydro-L-gulonate + NAD <> 2,3-Diketo-L-gulonate + NADH + Hydrogen ion 3-Dehydro-L-gulonate + NADP <> 2,3-Diketo-L-gulonate + NADPH + Hydrogen ion 3-Dehydro-L-gulonate + Adenosine triphosphate <> 3-Dehydro-L-gulonate 6-phosphate + ADP 3-Dehydro-L-gulonate + NAD < Hydrogen ion + 2,3-Diketo-L-gulonate + NADH 3-Dehydro-L-gulonate + NAD(P)(+) > (4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate + NAD(P)H Adenosine triphosphate + 3-Dehydro-L-gulonate > ADP + 3-Dehydro-L-gulonate 6-phosphate 3-Dehydro-L-gulonate + NAD + NADP <> 2,3-Diketo-L-gulonate + NADH + NADPH + Hydrogen ion 3-Dehydro-L-gulonate + Adenosine triphosphate > 3-keto-L-gulonate 6-phosphate + Adenosine diphosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate + ADP 2,3-Diketo-L-gulonate + NADH + Hydrogen ion + 2,3-Diketo-L-gulonate > 3-Dehydro-L-gulonate + NAD
SMPDB Pathways:	Ascorbate metabolism PW000793
KEGG Pathways:	Ascorbate and aldarate metabolism ec00053 Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:	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 (Non-derivatized) - 70eV, Positive splash10-0r29-9200000000-bfa5f284c8a99449827a View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive splash10-00ku-4401960000-e7040dc9b253756697ac 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 splash10-004j-2900000000-4ee99057131bac58d24b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0imi-9600000000-abad7f2422697e8886ed View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9100000000-7128eed92da683639fe8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-05bu-9800000000-2f48ad5aa2d38b4abf96 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0ap0-9500000000-96092591d92e04b163ef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4r-9100000000-833ef232e8c397c98dd3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00fr-9300000000-904e9656bc69e6510b01 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a6r-9100000000-dc8c8d7f3d7b9cbccc90 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-4026211091bf9f90ad00 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00dl-9700000000-a0000aecbfc4c59cdcd5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0cml-9200000000-df3574dae2a7dfc61329 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-08fr-9000000000-4d49c4220ff5afa3bdaf 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16142 HMDB ID HMDB06334 Pubchem Compound ID 439273 Kegg ID C00618 ChemSpider ID 388406 Wikipedia ID Not Available BioCyc ID 3-KETO-L-GULONATE EcoCyc ID 3-KETO-L-GULONATE

Enzymes