Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2019-11-26 02:56:30 UTC
Primary IDFDB001475
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Arabitol
DescriptionD-Arabitol is a polyol. Polyols are sugar alcohols linked to the pentose phosphate pathway (PPP). They are classified on the basis of the number of carbon atoms. Polyols occur in body fluids. A patient with leukoencephalopathy and peripheral neuropathy has been identified as suffering from ribose-5-phosphate isomerase (RPI) deficiency, a defect in the PPP. In this disorder, highly elevated concentrations of the C5 polyols such as D-arabitol are found in body fluids. In addition, transaldolase deficiency, another defect in the PPP, has been diagnosed in a patient with mainly liver problems among others had increased concentrations of polyols, mainly D-arabitol. So far, the pathophysiological role of polyols is relatively unknown. It is thought that D-arabitol is a metabolic end-product in humans. The strong brain-CSF-plasma gradient of polyols in the patient with RPI deficiency suggested a primary metabolic disorder. The mechanisms of brain and neuronal damage in RPI deficiency remain to be elucidated. A neurotoxic effect due to accumulation of the polyols may play a role. D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the Pentose and glucuronate interconversion pathway. (PMID: 16435225, J Inherit Metab Dis. 2005;28(6):1181-3).
CAS Number488-82-4
Structure
Thumb
Synonyms
SynonymSource
KlinitKegg
ArabitolMeSH
LyxitolMeSH
D-ArabinitolMeSH
L-ArabinitolMeSH
DL-ArabitolMeSH
(+--)-ArabitolMeSH
Arabitol, (D)-isomerMeSH
Arabitol, (L)-isomerMeSH
Arabino-pentitolMeSH
D-(+)-ArabitolHMDB
D-ArabinolHMDB
D-LyxitolHMDB
Arabinitolbiospider
Arabinitol, d-biospider
Arabitol, (d)biospider
Arabitol, d-biospider
D-(+)-arabinitolbiospider
D-(+)-arabitolbiospider
D-arabinitolbiospider
D-arabinolbiospider
D-lyxitolbiospider
Predicted Properties
PropertyValueSource
Water Solubility664 g/LALOGPS
logP-2.5ALOGPS
logP-3.1ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability14.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H12O5
IUPAC namepentane-1,2,3,4,5-pentol
InChI IdentifierInChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2
InChI KeyHEBKCHPVOIAQTA-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C(O)C(O)CO
Average Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
Classification
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point101-104 oC
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
EI-MSMass Spectrum (Electron Ionization)splash10-01vo-9000000000-f065454e8412613f8ecd2015-03-01View Spectrum
Predicted GC-MSD-Arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-9100000000-738016d8bd07caed9cccSpectrum
Predicted GC-MSD-Arabitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6033900000-a5ac27dc62580d112ccdSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ba-9500000000-67233150807800e941f02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01b9-9000000000-1ff17a8b87bbab9a36222012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-044i-9000000000-e0e330c8a899be718f602012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00m0-2900000000-c6b1101b88fa522fabd02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0zmr-9500000000-164d598431954fc1aeae2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0uki-9600000000-b90e9cee04cd0631b5992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00e9-2900000000-75413a29e8c6b3d9a6a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-c5cc931b9156365c4ca72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a5a-0900000000-94cf956e3f47a633d5722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03k9-0900000000-f0634d5b1d1f523b3caa2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-88c39e799daf7fb9dbca2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-66487a26d7047f9096a92015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-514c2ae8b98eb49941472015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9400000000-b3ca0d23907878fbe1a82015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9200000000-92a36674373a271da8672015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-5e7378c18473f82262822015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID804
ChEMBL IDCHEMBL1369426
KEGG Compound IDC01904
Pubchem Compound ID827
Pubchem Substance IDNot Available
ChEBI ID18333
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00568
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDD-ARABITOL
BIGG IDNot Available
KNApSAcK IDC00001156
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArabitol
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.