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Showing Compound Ribitol (FDB022083)

Record Information
Version1.0
Creation date2011-09-21 00:08:15 UTC
Update date2020-09-17 15:30:59 UTC
Primary IDFDB022083
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRibitol
DescriptionD-Arabitol or D-arabinitol, also known as klinit or lyxitol, belongs to the class of organic compounds known as sugar alcohols, a type of polyols. These are hydrogenated forms of carbohydrates in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. A polyol is an organic compound containing many hydroxyls. D-Arabitol is neutral compound. Polyols, classified by the number of carbon atoms and include the sugar alcohols, are linked to the pentose phosphate pathway (PPP). The PPP generates, NADPH and pentoses (5-carbon sugars) as well as ribose 5-phosphate, a precursor for the synthesis of nucleotides. While the pentose phosphate pathway oxidizes glucose, its primary role is anabolic rather than catabolic. Polyols, including D-arabitol, accumulates in body fluids in individuals with two defects in PPP, involving the enzymes ribose-5-phosphate isomerase (RPI) and transaldolase (PMID: 18987987). A patient with leukoencephalopathy and peripheral neuropathy, with a strong brain-CSF-plasma gradient of C5 polyols such as D-arabitol, was identified as suffering from RPI deficiency. Another patient displaying mainly liver problems and increased concentrations of polyols, mainly D-arabitol, was diagnosed with transaldolase deficiency. However, the mechanism of pathophysiology of polyols in patients with defects in the PPP is poorly understood. It is thought that D-arabitol is a metabolic end-product in humans. The mechanisms of brain and neuronal damage in RPI deficiency may result from polyol accumulation, causing secondary brain dysfunction (PMID: 16435225). D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the pentose and glucuronate interconversion pathway. D-Arabitol accumulated in a Penicillium rubens strain deleted of four highly expressed biosynthetic gene clusters that produce penicillin, roquefortine, chrysogine and fungisporin. The transcriptome of the P. rubens strain had changed when the gene cluster was removed, resulting in increased expression of D-arabinitol 4-dehydrogenase (PMID: 32376967). D-Arabitol, a fungal metabolite, is used as a marker for invasive candidiasis or infection by Candida fungal species (PMID: 15183861; PMID: 10647119). It is also a metabolite of Debaryomyces, Pichia and Zygosaccharomyces (PMID: 25809659).
CAS Number488-81-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Polarizability14.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H12O5
IUPAC name(2R,3s,4S)-pentane-1,2,3,4,5-pentol
InChI IdentifierInChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-
InChI KeyHEBKCHPVOIAQTA-ZXFHETKHSA-N
Isomeric SMILESOC[C@H](O)[C@H](O)[C@H](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
Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSRibitol, 5 TMS, GC-MS Spectrumsplash10-0fr2-0930000000-5a1a8471040df361537cSpectrum
GC-MSRibitol, non-derivatized, GC-MS Spectrumsplash10-0gba-0940000000-39c5ee90545f38856669Spectrum
GC-MSRibitol, 5 TMS, GC-MS Spectrumsplash10-00di-8941000000-a1eac40beaba679b545bSpectrum
GC-MSRibitol, 5 TMS, GC-MS Spectrumsplash10-00di-8930000000-85527d43cd5f10f959a8Spectrum
GC-MSRibitol, 5 TMS, GC-MS Spectrumsplash10-0gb9-0962000000-9c177252fb79fd04ff8cSpectrum
GC-MSRibitol, non-derivatized, GC-MS Spectrumsplash10-0fr2-0930000000-5a1a8471040df361537cSpectrum
GC-MSRibitol, non-derivatized, GC-MS Spectrumsplash10-0gba-0940000000-39c5ee90545f38856669Spectrum
GC-MSRibitol, non-derivatized, GC-MS Spectrumsplash10-00di-8941000000-a1eac40beaba679b545bSpectrum
GC-MSRibitol, non-derivatized, GC-MS Spectrumsplash10-00di-8930000000-85527d43cd5f10f959a8Spectrum
GC-MSRibitol, non-derivatized, GC-MS Spectrumsplash10-0gb9-0962000000-9c177252fb79fd04ff8cSpectrum
Predicted GC-MSRibitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-9100000000-738016d8bd07caed9cccSpectrum
Predicted GC-MSRibitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6033900000-a5ac27dc62580d112ccdSpectrum
Predicted GC-MSRibitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRibitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kb-9200000000-1c9444c33ee213e4aa4f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05mo-9000000000-baf46067df2ebf3b854c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-3276d3005611fd3d415c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-7db5e452cb762f33fd3a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-8900000000-5ee7c2252ae88c5c01982012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-47c7512c4671bb121a012012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-1900000000-b984613919de5add093c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0ufr-0901000000-616311fa40559ac618da2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-7900000000-c947bd6b615b2019d2552012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-c7e6bce3675a8cd1566b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-419f37e184ec82e4c1232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-8900000000-e69cc8758936cd2cbcea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-d6447ee4c80f85c44fef2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1900000000-67203d89ca337c3cd9d12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-7900000000-867bbfc363a4790dadc12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c7e6bce3675a8cd1566b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-419f37e184ec82e4c1232017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-fd63152f503ab1d4aa192017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-d230735907e604c9d45a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-91a543c0d92a8d8d3c3d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9300000000-e06ed1bf8e262afac25a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9100000000-b459e90a751cabc2a2312017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-4943c8a982ad5101e46f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zmr-9500000000-1887747b16d168b096092021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-83f8fb1c321a951b0e7e2021-09-21View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID10254628
ChEMBL IDCHEMBL3137744
KEGG Compound IDC00474
Pubchem Compound ID827
Pubchem Substance IDNot Available
ChEBI ID15963
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00508
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35086
KNApSAcK IDNot Available
HET IDRB0
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRibitol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference