dehydro-D-arabinono-1,4-lactone (YMDB00192)

Identification
YMDB IDYMDB00192
Namedehydro-D-arabinono-1,4-lactone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiondehydro-D-arabinono-1,4-lactone, also known as D-erythroascorbic acid or D-glycero-2-pentenono-L,4-lactone, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. dehydro-D-arabinono-1,4-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). dehydro-D-arabinono-1,4-lactone may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (5R)-3,4-Dihydroxy-5-(hydroxymethyl)furan-2(5H)-one
  • D-Erythroascorbic acid
  • D-Glycero-2-pentenono-L,4-lactone
  • D-Erythroascorbate
  • D-erythro-Ascorbic acid
  • D-erythro-Ascorbate
CAS numberNot Available
WeightAverage: 146.0981
Monoisotopic: 146.021523302
InChI KeyZZZCUOFIHGPKAK-UWTATZPHSA-N
InChIInChI=1S/C5H6O5/c6-1-2-3(7)4(8)5(9)10-2/h2,6-8H,1H2/t2-/m1/s1
IUPAC Name(5R)-3,4-dihydroxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-one
Traditional IUPAC Name(5R)-3,4-dihydroxy-5-(hydroxymethyl)-5H-furan-2-one
Chemical FormulaC5H6O5
SMILESOC[C@H]1OC(=O)C(O)=C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Monosaccharide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous acid
  • Lactone
  • Enediol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • 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 Solubility492 g/LALOGPS
logP-1.5ALOGPS
logP-1.3ChemAxon
logS0.53ALOGPS
pKa (Strongest Acidic)4.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.07 m³·mol⁻¹ChemAxon
Polarizability12.16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
D-arabinono-1,4-lactone + oxygen ↔ Hydrogen peroxide + dehydro-D-arabinono-1,4-lactone
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fml-9400000000-0d77717d2b9ce05e1490JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0092-4900000000-9ee98b4343f1aa95af8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-3900000000-d46dd03e3548f69a2e6fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9100000000-f44e59e90024a0f46dd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2900000000-f79f94d04fbe8375b1a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-2900000000-74bc961b219187ae72c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-a22b22eac355e6c2bab4JSpectraViewer
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
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Lee, B. H., Huh, W. K., Kim, S. T., Lee, J. S., Kang, S. O. (1999). "Bacterial production of D-erythroascorbic acid and L-ascorbic acid through functional expression of Saccharomyces cerevisiae D-arabinono-1,4-lactone oxidase in Escherichia coli." Appl Environ Microbiol 65:4685-4687.10508108
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17803
HMDB IDNot Available
Pubchem Compound ID993
Kegg IDC06316
ChemSpider ID20016055
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. D-arabinono-1,4-lactone oxidase
General function:
Involved in D-arabinono-1,4-lactone oxidase activity
Specific function:
Can oxidize L-gulono-1,4-lactone as well as D-arabinono- 1,4-lactone and L-galactono-1,4-lactone
Gene Name:
ALO1
Uniprot ID:
P54783
Molecular weight:
59493.19922
Reactions
D-arabinono-1,4-lactone + O(2) → dehydro-D-arabinono-1,4-lactone + H(2)O(2).