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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-16 09:36:44 UTC
Update Date2020-02-26 21:23:32 UTC
HMDB IDHMDB0001851
Secondary Accession Numbers
  • HMDB0000199
  • HMDB00199
  • HMDB01851
Metabolite Identification
Common NameL-Arabitol
DescriptionL-Arabitol, also known as L-arabinitol or L-lyxitol, is a member of the class of compounds known as sugar alcohols. Sugar alcohols 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. L-Arabitol is soluble (in water) and is a very weakly acidic compound (based on its pKa). L-Arabitol can be found in a number of food items such as sweet potato, deerberry, moth bean, and European chestnut, which makes L-arabitol a potential biomarker for the consumption of these food products. L-Arabitol can be found in most biofluids, including urine, cerebrospinal fluid (CSF), saliva, and blood. L-Arabitol exists in all living species, ranging from bacteria to humans. Moreover, L-arabitol is found to be associated with Alzheimer's disease and ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism. L-Arabitol can be formed by the reduction of either arabinose or lyxose. L-Arabitol has been reported in pentosuric acidemia (PMID: 13525419 ). L-Arabinosinuia has been described in a patient, presented at the age of 16 months with delayed motor development and facial dysmorphism (PMID: 12359133 ) Congenital liver cirrhosis has been recently described in a patient with highly elevated plasma and urine levels of arabitol due to transaldolase deficiency (Inherit Metab Dis 23(Suppl. 1):172, 2000).
Structure
Data?1582752212
Synonyms
ValueSource
L-ArabinolChEBI
L-LyxitolChEBI
L-ArabinitolKegg
Arabitol, (D)-isomerHMDB
D-ArabinitolHMDB
D-ArabitolHMDB
DL-ArabitolHMDB
Arabino-pentitolHMDB
ArabitolHMDB
(+--)-ArabitolHMDB
Arabitol, (L)-isomerHMDB
LyxitolHMDB
L(-)-ArabitolHMDB
1,2,3,4,5-PentahydroxypentaneHMDB
Adonite adonitolHMDB
ArabinitolHMDB
L-(+)-ArabitolHMDB
L-(-)-ArabinitolHMDB
L-(-)-ArabitolHMDB
L-ArabitolChEBI
Chemical FormulaC5H12O5
Average Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
IUPAC Name(2S,4S)-pentane-1,2,3,4,5-pentol
Traditional Namearabinitol
CAS Registry Number7643-75-6
SMILES
OC[C@H](O)C(O)[C@@H](O)CO
InChI Identifier
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m0/s1
InChI KeyHEBKCHPVOIAQTA-IMJSIDKUSA-N
Chemical Taxonomy
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point101 - 104 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability14.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0uxs-0930000000-6ef7d2f1643b576f6fbfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0930000000-6ef7d2f1643b576f6fbfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9100000000-51c1d4635c9c103902c4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0a4i-6033900000-a5ac27dc62580d112ccdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-6900000000-0ddb428b63c2d2c275b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0abl-9000000000-01b0114148e5ae6b5689Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-d30546aff0a9d5533991Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-4f856d537cc8252ecc47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-403bacad5117a30582dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-eb879b27e7b182cfe7c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9400000000-3db6454ab3e2315aa744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9200000000-b84c400427c7e44eb4ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c37624fb31a8cb33b163Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<3.947 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified28.9 +/- 8.5 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected and Quantified31.8 (10.2-64.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified50.0 (16.0-89.0) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified19.28 +/- 6.32 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified98.684 +/- 59.211 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified110.0 (32.0–198.0) uMAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified22.4 +/- 4.6 uMAdult (>18 years old)BothAlzheimer's disease details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified1300.0 (1021.0-1612.0) umol/mmol creatinineAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  1. Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [PubMed:14988808 ]
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Alzheimer's disease
  1. Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022709
KNApSAcK IDNot Available
Chemspider ID388391
KEGG Compound IDC00532
BioCyc IDL-ARABITOL
BiGG ID35268
Wikipedia LinkArabitol
METLIN ID141
PubChem Compound439255
PDB IDNot Available
ChEBI ID18403
Food Biomarker OntologyNot Available
VMH IDABT
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. TOUSTER O, HARWELL SO: The isolation of L-arabitol from pentosuric urine. J Biol Chem. 1958 Feb;230(2):1031-41. [PubMed:13525419 ]
  2. Onkenhout W, Groener JE, Verhoeven NM, Yin C, Laan LA: L-Arabinosuria: a new defect in human pentose metabolism. Mol Genet Metab. 2002 Sep-Oct;77(1-2):80-5. [PubMed:12359133 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
L-Arabitol + NAD → L-Arabinose + NADH + Hydrogen Iondetails
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Iondetails
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available
Reactions
L-Arabitol + NAD → L-Arabinose + NADH + Hydrogen Iondetails
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Iondetails