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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:31 -0600
Update Date	2015-06-04 16:52:57 -0600
Secondary Accession Numbers	ECMDB21376
Identification
Name:	L-Idonate
Description	L-idonate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. L-idonate is a metabolite in D-gluconate catabolism. The catabolic sequence for l-idonate is as follows: l-idonate is transported by the l-idonate transporter, IdnT; l-idonate is oxidized to 5-keto-gluconate (5KG) by l-idonate 5-dehydrogenase, IdnD; 5KG is reduced to d-gluconate by 5-keto-D-gluconate 5-reductase, IdnO; and d-gluconate is phosphorylated by a thermosensitive gluconate kinase, IdnK, to make 6-phosphogluconate (6PG), which is further catabolized via the Entner-Doudoroff pathway. Thus, IdnD and IdnO allow for the redox-coupled interconversion of l-idonate to d-gluconate via 5KG. The l-idonate catabolic pathway overlaps d-gluconate catabolism through the common intermediates d-gluconate and 6PG. (PMID: 14973046)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xae5b2508> Close
Synonyms:	L-Idonate L-Idonic acid
Chemical Formula:	C6H12O7
Weight:	Average: 196.1553 Monoisotopic: 196.058302738
InChI Key:	RGHNJXZEOKUKBD-SKNVOMKLSA-N
InChI:	InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5+/m0/s1
CAS number:	1114-17-6
IUPAC Name:	(2R,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexanoic acid
Traditional IUPAC Name:	L-idonic acid
SMILES:	[H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]([H])(O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Hydroxy acids and derivatives
Sub Class	Medium-chain hydroxy acids and derivatives
Direct Parent	Medium-chain hydroxy acids and derivatives
Alternative Parents	Medium-chain fatty acids Hydroxy fatty acids Beta hydroxy acids and derivatives Monosaccharides Alpha hydroxy acids and derivatives Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Medium-chain hydroxy acid Medium-chain fatty acid Beta-hydroxy acid Hydroxy fatty acid Alpha-hydroxy acid Monosaccharide Fatty acyl Fatty acid Secondary alcohol Polyol Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Organooxygen compound Hydrocarbon derivative Organic oxide Carbonyl group Primary alcohol Alcohol Organic oxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	idonic acid (CHEBI:21336 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 159 g/L ALOGPS logP -2.6 ALOGPS logP -3.4 ChemAxon logS -0.09 ALOGPS pKa (Strongest Acidic) 3.39 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 138.45 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 38.27 m³·mol⁻¹ ChemAxon Polarizability 17.02 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:	L-Idonate + NADP <> 5-Dehydro-D-gluconate + NADPH + Hydrogen ion NAD(P)<sup>+</sup> + L-Idonate <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion 2-keto-L-gulonate + NAD(P)H + Hydrogen ion > L-Idonate + NAD(P)<sup>+</sup> Hydrogen ion + 2-Dehydro-D-gluconate + NADPH <> L-Idonate + NADP L-Idonate + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)H L-Idonate + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion 2-Keto-L-gluconate + Hydrogen ion + NADPH + 2-Dehydro-D-gluconate + NADPH > NADP + L-Idonate L-Idonate + NADP > Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH + 5-Keto-D-gluconate
SMPDB Pathways:	ketogluconate metabolism PW002003
KEGG Pathways:	Not Available
EcoCyc Pathways:	L-idonate degradation IDNCAT-PWY ketogluconate metabolism KETOGLUCONMET-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004j-2900000000-2230427d193bbdea286d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-9500000000-d8d68bb3743d9921fc50 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0bvi-9100000000-ccfedd0f60a90274d462 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-05ic-9800000000-0ca5a02ddc6aa6467364 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052r-9400000000-eb28555aa63542892ef6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9100000000-ccfaef492473a4ca17de 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:	Bausch, C., Ramsey, M., Conway, T. (2004). "Transcriptional organization and regulation of the L-idonic acid pathway (GntII system) in Escherichia coli." J Bacteriol 186:1388-1397. Pubmed: 14973046 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
Links
External Links:	Resource Link CHEBI ID 17796 HMDB ID Not Available Pubchem Compound ID 604 Kegg ID C00770 ChemSpider ID 584 Wikipedia ID Not Available BioCyc ID L-IDONATE EcoCyc ID L-IDONATE

Enzymes

Transporters