Identification
YMDB IDYMDB00813
NameL-gulono-1,4-lactone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Gulonolactone 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. L-Gulonolactone exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on L-Gulonolactone.
Structure
Thumb
Synonyms
  • gamma-gulonolactone
  • L-(+)-Gulono-1,4-lactone
  • l-gulonic acid gamma-lactone
  • L-Gulonic gamma-lactone
  • L-Gulono-1,4-lactone
  • l-gulono-gamma-lactone
  • l-gulonolactone
  • g-Gulonolactone
  • Γ-gulonolactone
  • L-Gulonate g-lactone
  • L-Gulonate gamma-lactone
  • L-Gulonate γ-lactone
  • L-Gulonic acid g-lactone
  • L-Gulonic acid γ-lactone
  • L-Gulono-g-lactone
  • L-Gulono-γ-lactone
  • Reduced ascorbate
  • Reduced ascorbic acid
  • Gulonolactone, (L)-isomer
  • Gulonolactone
  • Gulonolactone, (D)-isomer
  • Dihydroascorbic acid
  • L-(+)-Gulonic acid gamma-lactone
  • L-(+)-Gulonic acid γ-lactone
CAS number1128-23-0
WeightAverage: 178.14
Monoisotopic: 178.047738052
InChI KeySXZYCXMUPBBULW-SKNVOMKLSA-N
InChIInChI=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
IUPAC Name(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
Traditional IUPAC NameL-gulonolactone
Chemical FormulaC6H10O6
SMILES[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-2.571PhysProp
Predicted Properties
PropertyValueSource
Water Solubility637 g/LALOGPS
logP-2ALOGPS
logP-2.7ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.78 m³·mol⁻¹ChemAxon
Polarizability15.47 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gc0-2961000000-10e3ffe56d1491c35d8aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gc0-2961000000-10e3ffe56d1491c35d8aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0930000000-725e277ca1152a7fbc98JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-9400000000-615dd94b06b3e5e78526JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0pk9-5359600000-e93f868058ca84374468JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ec8c949182af76945e86JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-7a0472476f07853a992bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a70-9300000000-74777b41198e9cd46262JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-06ds-9000000000-2d40464867d71e6c1135JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01b9-9400000000-d5de17e2c0c42a02efc0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-0435329cc0eb001898faJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-1900000000-f47818211aa007edc5f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-c7c9eb2eaa1f91ac9951JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-072c615a4ace0aca930aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-3900000000-5f8e27814cf4a835d41aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ar0-6900000000-9a9aef2bcc37f743beabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9100000000-4892df7d8d2a53c17d7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9300000000-cd9f8103b846d70baac0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-650b3c2ec9303d9b2a96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-232c502ee9a5b93d5a17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fu-1900000000-a9b5237063a8327d87cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-9500000000-aadb547d81673dce1915JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mm-9100000000-0a3f8e5a08a10aa888ebJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Sauer, M., Branduardi, P., Valli, M., Porro, D. (2004). "Production of L-ascorbic acid by metabolically engineered Saccharomyces cerevisiae and Zygosaccharomyces bailii." Appl Environ Microbiol 70:6086-6091.15466554
  • Nishikimi, M., Noguchi, E., Yagi, K. (1978). "Occurrence in yeast of L-galactonolactone oxidase which is similar to a key enzyme for ascorbic acid biosynthesis in animals, L-gulonolactone oxidase." Arch Biochem Biophys 191:479-486.369458
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17587
HMDB IDHMDB03466
Pubchem Compound ID439373
Kegg IDC01040
ChemSpider ID23936497
FOODB IDFDB023179
Wikipedia IDL-gulonolactone oxidase
BioCyc ID2-KETO-L-GULONOLACTONE