L-Xylo-hexulonolactone (YMDB00800)

Identification
YMDB IDYMDB00800
NameL-Xylo-hexulonolactone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Xylo-hexulonolactone 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-Xylo-hexulonolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Xylo-hexulonolactone may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • L-xylo-Hex-2-ulono-1,4-lactone
  • L-xylo-Hex-3-ulono-1,4-lactone
  • L-xylo-Hexulonolactone
CAS numberNot Available
WeightAverage: 176.1241
Monoisotopic: 176.032087988
InChI KeyPJBQWWHYTVYMLO-MDZRLIFHSA-N
InChIInChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,4-5,7-8,10H,1H2/t2-,4-,5+/m0/s1
IUPAC Name(3S,5R)-5-[(1S)-1,2-dihydroxyethyl]-3-hydroxyoxolane-2,4-dione
Traditional IUPAC NameL-xylo-hex-3-ulonolactone
Chemical FormulaC6H8O6
SMILES[H][C@@]1(OC(=O)[C@@H](O)C1=O)[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
  • 3-furanone
  • Gamma butyrolactone
  • 1,3-dicarbonyl compound
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility466 g/LALOGPS
logP-1.6ALOGPS
logP-2ChemAxon
logS0.42ALOGPS
pKa (Strongest Acidic)8.03ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.09 m³·mol⁻¹ChemAxon
Polarizability14.72 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9300000000-12edc9e854b5d3fb3586JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-e1a2060288dfa69a7ec8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvl-4900000000-74e70c33e8c3508563faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-1d099791076040e7718bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02di-2900000000-fa7a82a4c6641c430ce9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-4900000000-98c1a460a58345baee05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9300000000-e00125e18c3f7a734652JSpectraViewer
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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28745
HMDB IDNot Available
Pubchem Compound ID5461125
Kegg IDC03289
ChemSpider ID23101539
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available