Record Information
Version1.0
Creation date2010-04-08 22:04:53 UTC
Update date2020-09-17 15:30:13 UTC
Primary IDFDB001218
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArabinose
DescriptionArabinose or L-arabinose is an aldopentose, a monosaccharide with an aldehyde functional group. Although most saccharides have the D-form, arabinose is most abundant in the L-form. It is colorless with a prism or needle like crystal that is very soluble in water. It has a sweet taste. It is one of the most abundant components released after complete hydrolysis of non-starch polysaccharides (NSP) from vegetables. However, NSPs which include cellulose, hemi-cellulose, pectin, and oligosaccharides, are complicated compounds both in physical structure and chemical composition. The NSPs are resistant to the digestive enzymes and pass to the hindgut where microbial degradation takes place. When L-arabinose is ingested, it is absorbed from the intestinal tract at a lower rate than glucose with a portion excreted in the urine. Although widely present in nature, L-arabinose is rarely used, and its physiological effects in vivo have received little attention. L-arabinose selectively inhibits intestinal sucrase activity in a non-competitive manner and suppresses the plasma glucose increase after sucrose ingestion (PMID: 8931641). Because the intestinal absorption of sucrose is inhibited in the presence of L-arabinose, the absorption of sucrose should be reduced by arabinose ingestion. Most of the studies reported so far on the absorption and utilization of L-arabinose have been with non human omnivore animal (PMID:11238761; PMID: 1390604). In a rare published case, two autistic brothers, with no known metabolic disease, had nearly six times greater L-arabinose(179 µmol/mmol creatinine) in their urine compared to normal children (PMID: 7628083). L-Arabinose was elevated in the CSF and urine of patients with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism (PMID: 14988808). L-Arabinose is also a microbial metabolite found in Mycobacterium (PMID: 16232643).
CAS Number147-81-9
Structure
Thumb
Synonyms
SynonymSource
(2S,3R,4R)-2,3,4,5-TetrahydroxypentanalChEBI
(+/-)-arabinoseHMDB
Aloe sugarHMDB
AloinoseHMDB
DL-ArabinoseHMDB
PectinoseHMDB
D-ArabinoseChEBI
(±)-Arabinosemanual
Predicted Properties
PropertyValueSource
Water Solubility380 g/LALOGPS
logP-2.3ALOGPS
logP-2.9ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)12.33ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H10O5
IUPAC name(2S,3R,4R)-2,3,4,5-tetrahydroxypentanal
InChI IdentifierInChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1
InChI KeyPYMYPHUHKUWMLA-WDCZJNDASA-N
Isomeric SMILESOC[C@@H](O)[C@@H](O)[C@H](O)C=O
Average Molecular Weight150.1299
Monoisotopic Molecular Weight150.05282343
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 40.00%; H 6.71%; O 53.28%DFC
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSArabinose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9100000000-3d844ea1b588172feaf0Spectrum
Predicted GC-MSArabinose, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i0-6249400000-6324b88618b9174f1ee5Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-08mi-9100000000-fdc6cb3672d0fd9782e4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-0a4i-9000000000-8b4cbdfdbd1d64750afcSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-0002-1900000000-a6fad2b086e4d72e6455Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, negativesplash10-000j-9500000000-7f3c671f5a2325c13521Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, negativesplash10-052r-9000000000-4607894e05698b4efd4bSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, negativesplash10-0a4r-9000000000-7713ba3bfd41873ed05bSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 14V, negativesplash10-0a4i-9000000000-19cc19a6070f8904f223Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 17V, negativesplash10-0a4i-9000000000-cbfe90fac8fd1f09d178Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-0a4i-9000000000-194cea61e7f4bb116108Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-001i-2900000000-0431fbb715edbb5c2854Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-001i-0900000000-9b7382416823533b7db1Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-001i-0900000000-b354fa776d3c927b52a8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-001i-1900000000-4f54308f655454dcf238Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-001i-2900000000-ffb4e5e554a72f34fd7bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-001i-4900000000-df24839373685cc97976Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-001r-7900000000-08514302c6b21ad9497cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-008i-9700000000-9b73d2467b158cb7fe64Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00dr-9300000000-80b57725a8299b2e9afaSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00dr-9100000000-f5eb0b039697ddead9f8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-f8b9c6d77ac7485b2a13Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-c381cba09705c9d22367Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-157eda9875c5cd43b332Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-8bb17d4c0bc5362b2610Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-9200000000-f20b8cc45d0196859991Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-83841c4e2cbd5aa6df09Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID22599
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31467
CRC / DFC (Dictionary of Food Compounds) IDBWQ11-M:BWQ11-M
EAFUS IDNot Available
Dr. Duke IDARABINOSE|ARABINOSIDE
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 IDArabinose
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).