Record Information
Version1.0
Creation date2010-04-08 22:07:07 UTC
Update date2019-11-27 17:12:26 UTC
Primary IDFDB006401
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Arabinono-1,4-lactone
DescriptionD-arabinono-1,4-lactone, also known as D-arabinonic acid, gamma-lactone, is a member of the class of compounds known as pentoses. Pentoses are monosaccharides in which the carbohydrate moiety contains five carbon atoms. D-arabinono-1,4-lactone is soluble (in water) and a very weakly acidic compound (based on its pKa). D-arabinono-1,4-lactone can be found in rice, which makes D-arabinono-1,4-lactone a potential biomarker for the consumption of this food product. D-arabinono-1,4-lactone may be a unique S.cerevisiae (yeast) metabolite.
CAS Number2782-09-4
Structure
Thumb
Synonyms
SynonymSource
1,4-D-ArabinonolactoneChEBI
D-Arabinonic acid, gamma-lactoneChEBI
D-ArabonolactoneChEBI
D-Arabinonate, g-lactoneGenerator
D-Arabinonate, gamma-lactoneGenerator
D-Arabinonate, γ-lactoneGenerator
D-Arabinonic acid, g-lactoneGenerator
D-Arabinonic acid, γ-lactoneGenerator
D-ARABINO-1,4-LACTONEdb_source
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
Chemical FormulaC5H8O5
IUPAC name(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
InChI IdentifierInChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4+/m1/s1
InChI KeyCUOKHACJLGPRHD-JJYYJPOSSA-N
Isomeric SMILESOC[C@H]1OC(=O)[C@@H](O)[C@@H]1O
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gc0-2940000000-da4e93a8e3f86a2e55efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9200000000-57923aebd9b821766513View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-2900000000-d76c6c2ab2d323f65be1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-2900000000-ef1350e75a002dfbd727View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-9100000000-d00950097b42e8ee674eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-e97c530b9495b6c0d26aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-2900000000-bbbd4b6af81d996ce75dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ca903cf3d2c2e5bee97dView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00652
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID16292
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDD-ARABINO-1,4-LACTONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).