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Record Information
Version	2.0
Creation Date	2012-08-09 09:25:08 -0600
Update Date	2015-06-03 17:21:38 -0600
Secondary Accession Numbers	ECMDB21494
Identification
Name:	3-Keto-L-gulonic acid
Description	3-keto-L-gulonic acid is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. 3-keto-L-gulonic acid is invovled in Ascorbic acid degradation.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa33c5bb0> Close
Synonyms:	2-Keto-L-gulonate 2-Keto-L-gulonic acid 2-Oxo-L-gulonate 2-Oxo-L-gulonic acid 3-Keto-L-Gulonate 3-Keto-L-Gulonic acid L-Sorbosonate L-Sorbosonic acid L-Xylo-2-Hexulosonate L-Xylo-2-Hexulosonic acid L-Xylo-hex-2-ulosonate L-Xylo-hex-2-ulosonic acid L-Xylohexulosonate L-Xylohexulosonic acid
Chemical Formula:	C6H10O7
Weight:	Average: 194.1394 Monoisotopic: 194.042652674
InChI Key:	VBUYCZFBVCCYFD-NUNKFHFFSA-N
InChI:	InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-4,7-10H,1H2,(H,12,13)/t2-,3+,4-/m0/s1
CAS number:	526-98-7
IUPAC Name:	(3S,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexanoic acid
Traditional IUPAC Name:	2-keto-L-gulonic acid
SMILES:	[H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=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 hydroxy acids and derivatives Beta-hydroxy ketones Alpha-keto acids and derivatives Acyloins 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-hydroxy acid Sugar acid Acyloin Alpha-keto acid Beta-hydroxy ketone Hydroxy acid Keto acid 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:19543 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	171 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 101 g/L ALOGPS logP -2.4 ALOGPS logP -2.5 ChemAxon logS -0.28 ALOGPS pKa (Strongest Acidic) 2.67 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 37.65 m³·mol⁻¹ ChemAxon Polarizability 16.23 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:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS) splash10-0udi-1920000000-82856fabc63f1e5fc70c View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS) splash10-0uxr-1941000000-db1492f9443cc9e94eb2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004j-1900000000-4c70f69302f31c33ee5c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0ik9-9600000000-f027c92665e4c348f2a7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0bt9-9100000000-97f3ffedc2a208b66d5e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0feu-8900000000-bc1bb85704615258ff49 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0pbi-9400000000-004d1425c619a87cd240 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4r-9100000000-d0a0104e3be31e2d9161 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:	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 19543 HMDB ID Not Available Pubchem Compound ID 102424 Kegg ID C15673 ChemSpider ID 92502 Wikipedia ID Not Available BioCyc ID Not Available

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