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Identification
YMDB IDYMDB00014
NameD-arabinono-1,4-lactone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Arabinono-1,4-lactone is also known as 1,4-D-arabinonolactone or D-arabinonate, g-lactone. D-Arabinono-1,4-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Arabinono-1,4-lactone may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • 1,4-D-Arabinonolactone
  • D-Arabinonate, g-lactone
  • D-Arabinonate, gamma-lactone
  • D-Arabinonate, γ-lactone
  • D-Arabinonic acid, g-lactone
  • D-Arabinonic acid, gamma-lactone
  • D-Arabinonic acid, γ-lactone
  • D-Arabinono-1,4-lactone
  • D-Arabonolactone
CAS number2782-09-4
WeightAverage: 148.114
Monoisotopic: 148.037173366
InChI KeyCUOKHACJLGPRHD-JJYYJPOSSA-N
InChIInChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4+/m1/s1
IUPAC Name(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
Traditional IUPAC NameD-arabinono-1,4-lactone
Chemical FormulaC5H8O5
SMILESOC[C@H]1OC(=O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • 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 Solubility847 g/LALOGPS
logP-2ALOGPS
logP-2.1ChemAxon
logS0.76ALOGPS
pKa (Strongest Acidic)11.63ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.82 m³·mol⁻¹ChemAxon
Polarizability12.81 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
NAD + D-ArabinoseD-arabinono-1,4-lactone + NADH + hydron
NADP + D-ArabinoseD-arabinono-1,4-lactone + NADPH + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gc0-2940000000-da4e93a8e3f86a2e55efJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9200000000-57923aebd9b821766513JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-2900000000-d76c6c2ab2d323f65be1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-2900000000-ef1350e75a002dfbd727JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-9100000000-d00950097b42e8ee674eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-e97c530b9495b6c0d26aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-2900000000-bbbd4b6af81d996ce75dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ca903cf3d2c2e5bee97dJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • 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
  • Amako, K., Fujita, K., Shimohata, T. A., Hasegawa, E., Kishimoto, R., Goda, K. (2006). "NAD+-specific D-arabinose dehydrogenase and its contribution to erythroascorbic acid production in Saccharomyces cerevisiae." FEBS Lett 580:6428-6434.17097644
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16292
HMDB IDNot Available
Pubchem Compound ID17723
Kegg IDC00652
ChemSpider ID23936492
FOODB IDFDB006401
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of D-arabinose, L-xylose, L- fucose and L-galactose in the presence of NADP+
Gene Name:
ARA1
Uniprot ID:
P38115
Molecular weight:
38883.19922
Reactions
D-arabinose + NAD(P)(+) → D-arabinono-1,4-lactone + NAD(P)H.
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).
General function:
Involved in oxidoreductase activity
Specific function:
D-arabinose + NAD(+) = D-arabinono-1,4-lactone + NADH
Gene Name:
ARA2
Uniprot ID:
Q04212
Molecular weight:
38220.0
Reactions
D-arabinose + NAD(+) → D-arabinono-1,4-lactone + NADH.