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Identification
YMDB IDYMDB00654
NameD-Arabinose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Arabinose, also known as (+/-)-arabinose or aloe sugar, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. D-Arabinose is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • D-Ara
  • D-Arabinose
  • Pentopyranose
  • (2S,3R,4R)-2,3,4,5-Tetrahydroxypentanal
  • (+/-)-arabinose
  • Aloe sugar
  • Aloinose
  • DL-Arabinose
  • Pectinose
CAS number10323-20-3
WeightAverage: 150.1299
Monoisotopic: 150.05282343
InChI KeyPYMYPHUHKUWMLA-WDCZJNDASA-N
InChIInChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1
IUPAC Name(2S,3R,4R)-2,3,4,5-tetrahydroxypentanal
Traditional IUPAC Namearabinose
Chemical FormulaC5H10O5
SMILES[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C=O
Chemical Taxonomy
Description 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
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point164-165 ºC
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility380 g/LALOGPS
logP-2.3ALOGPS
logP-2.9ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)11.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.38 m³·mol⁻¹ChemAxon
Polarizability13.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-3d844ea1b588172feaf0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-05i0-6249400000-6324b88618b9174f1ee5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-f8b9c6d77ac7485b2a13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-c381cba09705c9d22367JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-157eda9875c5cd43b332JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-8bb17d4c0bc5362b2610JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-9200000000-f20b8cc45d0196859991JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-83841c4e2cbd5aa6df09JSpectraViewer
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
  • Hancock, R. D., Galpin, J. R., Viola, R. (2000). "Biosynthesis of L-ascorbic acid (vitamin C) by Saccharomyces cerevisiae." FEMS Microbiol Lett 186:245-250.10802179
  • 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 ID17108
HMDB IDHMDB0029942
Pubchem Compound ID6902
Kegg IDC00216
ChemSpider ID59687
FOODB IDFDB001219
WikipediaArabinose
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 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.