1.0 2011-09-21 00:25:49 UTC 2015-07-21 06:57:34 UTC FDB023179 L-Gulonolactone L-Gulonolactone (also known as reduced ascorbic acid, RAA) is the substrate of the enzyme L-gulono-1,4-lactone oxidoreductase (EC 1.1.3.8), which catalyzes the last step of the biosynthesis of L-ascorbic acid (vitamin C) in plants and animals. The enzyme L-Gulono-1,4-lactone oxidase is missing in scurvy-prone, vitamin C-deficient animals, such as humans. L-Gulonolactone is present in human blood and has been used as one of the markers to compare changes in exercise-induced oxidative stress. (PMID: 16956367, 16494601) [HMDB] g-Gulonolactone gamma-Gulonolactone L-(+)-Gulono-1,4-lactone L-Gulonate g-lactone L-Gulonate gamma-lactone L-Gulonate γ-lactone L-Gulonic acid g-lactone L-Gulonic acid gamma-lactone L-Gulonic acid γ-lactone L-Gulono-1,4-lactone L-Gulono-g-lactone L-Gulono-gamma-lactone L-Gulono-γ-lactone Reduced ascorbate Reduced ascorbic acid γ-gulonolactone C6H10O6 178.14 178.047738052 (3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one L-gulonolactone 1128-23-0 [H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1 SXZYCXMUPBBULW-SKNVOMKLSA-N belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Gamma butyrolactones Organic compounds Organoheterocyclic compounds Lactones Gamma butyrolactones Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Primary alcohols Secondary alcohols Tetrahydrofurans Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Gamma butyrolactone Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Primary alcohol Secondary alcohol Tetrahydrofuran gulonolactone Solid logp -2.05 ALOGPS logs 0.55 ALOGPS solubility 6.37e+02 g/l ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 11.62 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one ChemAxon average_mass 178.14 ChemAxon mono_mass 178.047738052 ChemAxon smiles [H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO ChemAxon formula C6H10O6 ChemAxon inchi InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1 ChemAxon inchikey SXZYCXMUPBBULW-SKNVOMKLSA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 34.78 ChemAxon polarizability 15.47 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1645 Specdb::CMs 2600 Specdb::CMs 31464 Specdb::CMs 31822 Specdb::CMs 38610 Specdb::CMs 162518 Specdb::MsIr 1990 Specdb::MsIr 1991 Specdb::MsIr 1992 Specdb::NmrOneD 4972 Specdb::NmrOneD 4973 Specdb::NmrOneD 149540 Specdb::NmrOneD 149541 Specdb::NmrOneD 149542 Specdb::NmrOneD 149543 Specdb::NmrOneD 149544 Specdb::NmrOneD 149545 Specdb::NmrOneD 149546 Specdb::NmrOneD 149547 Specdb::NmrOneD 149548 Specdb::NmrOneD 149549 Specdb::NmrOneD 149550 Specdb::NmrOneD 149551 Specdb::NmrOneD 149552 Specdb::NmrOneD 149553 Specdb::NmrOneD 149554 Specdb::NmrOneD 149555 Specdb::NmrOneD 149556 Specdb::NmrOneD 149557 Specdb::NmrOneD 149558 Specdb::NmrOneD 149559 Specdb::MsMs 46437 Specdb::MsMs 46438 Specdb::MsMs 46439 Specdb::MsMs 158121 Specdb::MsMs 158122 Specdb::MsMs 158123 Specdb::MsMs 2227246 Specdb::MsMs 2227477 Specdb::MsMs 2232095 Specdb::MsMs 2232112 Specdb::MsMs 2234428 Specdb::MsMs 2234498 Specdb::MsMs 2769497 Specdb::MsMs 2769498 Specdb::MsMs 2769499 Specdb::MsMs 2912837 Specdb::MsMs 2912838 Specdb::MsMs 2912839 HMDB03466 17587 #<Reference:0x000055ce32126370> #<Reference:0x000055ce321261b8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823