2.0 2012-08-09 09:16:15 -0600 2015-06-03 17:21:30 -0600 ECMDB21440 M2MDB001835 Galactonolactone 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) 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 C6H10O6 178.14 178.047738052 (3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one galactonolactone 2426-46-2 O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O 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 WTXGYGWMPUGBAL-MGCNEYSASA-N Solid logp -2.29 ALOGPS logs 0.51 ALOGPS solubility 5.83e+02 g/l ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 11.61 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one ChemAxon average_mass 178.14 ChemAxon mono_mass 178.047738052 ChemAxon smiles O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O ChemAxon formula C6H10O6 ChemAxon 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 ChemAxon inchikey WTXGYGWMPUGBAL-MGCNEYSASA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 34.78 ChemAxon polarizability 14.99 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 13543 Specdb::CMs 38439 Specdb::CMs 170276 Specdb::NmrOneD 122658 Specdb::NmrOneD 122659 Specdb::NmrOneD 122660 Specdb::NmrOneD 122661 Specdb::NmrOneD 122662 Specdb::NmrOneD 122663 Specdb::NmrOneD 122664 Specdb::NmrOneD 122665 Specdb::NmrOneD 122666 Specdb::NmrOneD 122667 Specdb::NmrOneD 122668 Specdb::NmrOneD 122669 Specdb::NmrOneD 122670 Specdb::NmrOneD 122671 Specdb::NmrOneD 122672 Specdb::NmrOneD 122673 Specdb::NmrOneD 122674 Specdb::NmrOneD 122675 Specdb::NmrOneD 122676 Specdb::NmrOneD 122677 Specdb::MsMs 26708 Specdb::MsMs 26709 Specdb::MsMs 26710 Specdb::MsMs 33266 Specdb::MsMs 33267 Specdb::MsMs 33268 Specdb::MsMs 2784619 Specdb::MsMs 2784620 Specdb::MsMs 2784621 Specdb::MsMs 2921605 Specdb::MsMs 2921606 Specdb::MsMs 2921607 HMDB02541 151006 133098 C03383 15895 D-GALACTONO-1-4-LACTONE 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. 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. 18331064 Huber, R. E., Brockbank, R. L. (1987). "Strong inhibitory effect of furanoses and sugar lactones on beta-galactosidase Escherichia coli." Biochemistry 26:1526-1531. 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. 1797843 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. 699273