L-gulono-1,4-lactone (PAMDB120422)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120422
Identification
Name: L-gulono-1,4-lactone
Description:The furanose form of gulonolactone having L-configuration.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • gamma-Gulonolactone
  • L-Gulonic acid gamma-lactone
  • L-gulono-1,4-lactone
  • L-Gulono-1,4-lactone
  • L-Gulono-gamma-lactone
  • L-Gulonolactone
Chemical Formula: C6H10O6
Average Molecular Weight: 178.141
Monoisotopic Molecular Weight: 178.04774
InChI Key: SXZYCXMUPBBULW-SKNVOMKLSA-N
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
CAS number: 1128-23-0
IUPAC Name:(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxydihydrofuran-2(3H)-one
Traditional IUPAC Name: L-gulonolactone
SMILES:C(C([CH]1(C(C(C(O1)=O)O)O))O)O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as gamma butyrolactones. These 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassLactones
Direct Parent Gamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Oxolane
  • 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 Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.571Not Available
Predicted Properties
PropertyValueSource
Water Solubility637.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.78 m3·mol-1ChemAxon
Polarizability15.56 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
L-gulono-1,4-lactone + Water → L-gulonate + Hydrogen ion
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gc0-2961000000-10e3ffe56d1491c35d8aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • Wolucka BA, Communi D (2006)Mycobacterium tuberculosis possesses a functional enzyme for the synthesis of vitamin C, L-gulono-1,4-lactone dehydrogenase. The FEBS journal 273, Pubmed: 16956367
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
METABOLIGHTSMTBLC17587
HMDBHMDB03466
CHEMSPIDER388493
CHEBI17587
PUBCHEM439373
LIGAND-CPDC01040