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Record Information
Version	2.0
Creation Date	2012-08-09 09:16:15 -0600
Update Date	2015-06-03 17:21:30 -0600
Secondary Accession Numbers	ECMDB21440
Identification
Name:	Galactonolactone
Description	Galactonolactone is a lactone formed from galactonic acid/galactonate. There are different isomers of galactonolactone, including structural isomers with different numbers of carbons in the lactone ring (up to 6 carbons), and also D/L enantiomers for certain structural isomers. (ChEBI, PubChem, inferred from compound structures) In E. coli, both the D and L enantiomers of galactono-1,4-lactone (with 4 carbons in the lactone ring) can be found. (EcoCyc) D-galactono-1,5-lactone (with 5 carbons in the lactone ring) has been shown to have a strong inhibitory effect on E. coli beta-galactosidase. (PMID 3109465)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0x6570555c> Close
Synonyms:	γ-D-galactonolactone D-(-)-Galactonate γ-lactone D-(-)-galactonic acid γ-lactone D-Galactonate γ-lactone D-Galactonate g-lactone D-galactonate-γ-lactone D-galactonic acid γ-lactone D-galactonic acid g-lactone D-Galactonic acid-γ-lactone D-galactono-γ-lactone D-Galactono-1,4-lactone D-Galactono-1,5-lactone D-Galactono-8-lactone D-Galactonolactone Delta-Galactono-1,4-lactone Delta-Galactono-1,5-lactone Delta-Galactono-8-lactone Delta-Galactonolactone g-D-Galactonolactone g-delta-Galactonolactone g-δ-Galactonolactone Galactono-γ-lactone Gamma-D-Galactonolactone Gamma-delta-Galactonolactone γ-D-Galactonolactone γ-δ-Galactonolactone δ-galactono-1,4-Lactone δ-galactono-1,5-Lactone δ-galactono-8-Lactone δ-Galactonolactone
Chemical Formula:	C6H10O6
Weight:	Average: 178.14 Monoisotopic: 178.047738052
InChI Key:	WTXGYGWMPUGBAL-MGCNEYSASA-N
InChI:	InChI=1S/C6H10O6/c7-2-1-12-6(11)5(10)4(9)3(2)8/h2-5,7-10H,1H2/t2-,3+,4+,5-/m1/s1
CAS number:	2426-46-2
IUPAC Name:	(3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one
Traditional IUPAC Name:	galactonolactone
SMILES:	O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Lactones
Sub Class	Not Available
Direct Parent	Lactones
Alternative Parents	Oxepanes Secondary alcohols Carboxylic acid esters Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Caprolactone Oxepane Carboxylic acid ester Lactone Secondary alcohol Carboxylic acid derivative Monocarboxylic acid or derivatives Oxacycle Polyol Hydrocarbon derivative Organic oxide Alcohol Organooxygen compound Organic oxygen compound Carbonyl group Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 583 g/L ALOGPS logP -2.3 ALOGPS logP -2.7 ChemAxon logS 0.51 ALOGPS pKa (Strongest Acidic) 11.61 ChemAxon pKa (Strongest Basic) -3.5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 107.22 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 34.78 m³·mol⁻¹ ChemAxon Polarizability 14.99 ų ChemAxon Number of Rings 1 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 Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-06rl-9400000000-9e4502053b3fe09f123e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-0kou-3279300000-1418a34fa3efbbb205d1 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 splash10-01t9-0900000000-685a5dbb4f8a7102dcc5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03fr-2900000000-83611a0f9b640623ac24 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9200000000-fbfa10412acfeb6c4811 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-1900000000-61baef021fc455ee67ea View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-056r-2900000000-9c6963bd735f92051d97 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9100000000-4f71f72cc2972d6c238b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-4af21996c208dcba14ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03fu-9500000000-ac5d2741d49de16a664a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0btc-9000000000-0a9b1531d89f4242cbcb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-1900000000-9622261df6835436c4f0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0abc-9200000000-3d5e0ea9ad8151fc6cc0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9000000000-8c8e168512fbb0f52fa3 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:	Gates SC, Sweeley CC, Krivit W, DeWitt D, Blaisdell BE: Automated metabolic profiling of organic acids in human urine. II. Analysis of urine samples from "healthy" adults, sick children, and children with neuroblastoma. Clin Chem. 1978 Oct;24(10):1680-9. Pubmed: 699273 Huber, R. E., Brockbank, R. L. (1987). "Strong inhibitory effect of furanoses and sugar lactones on beta-galactosidase Escherichia coli." Biochemistry 26:1526-1531. Pubmed: 3109465 Rakotomanga S, Baillet A, Pellerin F, Baylocq-Ferrier D: Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia. J Chromatogr. 1991 Oct 4;570(2):277-84. Pubmed: 1797843 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 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 15895 HMDB ID HMDB02541 Pubchem Compound ID 151006 Kegg ID C03383 ChemSpider ID 133098 Wikipedia ID Not Available BioCyc ID D-GALACTONO-1-4-LACTONE EcoCyc ID D-GALACTONO-1-4-LACTONE