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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
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 + oxygenHydrogen peroxide + dehydro-D-arabinono-1,4-lactone
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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).