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Record Information
Version3.6
Creation Date2006-02-16 09:36:44 UTC
Update Date2016-02-11 01:05:00 UTC
HMDB IDHMDB01851
Secondary Accession Numbers
  • HMDB00199
Metabolite Identification
Common NameL-Arabitol
DescriptionL-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
Thumb
Synonyms
ValueSource
L-ArabinolChEBI
L-ArabitolChEBI
L-LyxitolChEBI
L(-)-ArabitolHMDB
1,2,3,4,5-PentahydroxypentaneHMDB
Adonite adonitolHMDB
ArabinitolHMDB
L-(+)-ArabitolHMDB
L-(-)-ArabinitolHMDB
L-(-)-ArabitolHMDB
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 KeyInChIKey=HEBKCHPVOIAQTA-IMJSIDKUSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar alcohols
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
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 Solubility664.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m3·mol-1ChemAxon
Polarizability14.28 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0uxs-0930000000-6ef7d2f1643b576f6fbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-6900000000-0ddb428b63c2d2c275b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0abl-9000000000-01b0114148e5ae6b5689View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-d30546aff0a9d5533991View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>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
BiofluidStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified1300.0 (1021.0-1612.0) umol/mmol creatinineAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency details
Associated Disorders and Diseases
Disease References
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. [8595727 ]
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. [14988808 ]
Associated OMIM IDs
  • 608611 (Ribose-5-phosphate isomerase deficiency)
  • 104300 (Alzheimer's disease)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022709
KNApSAcK IDNot Available
Chemspider ID388391
KEGG Compound IDC00532
BioCyc IDL-ARABITOL
BiGG ID35268
Wikipedia LinkAdonitol
NuGOwiki LinkHMDB01851
Metagene LinkHMDB01851
METLIN ID141
PubChem Compound439255
PDB IDNot Available
ChEBI ID18403
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [12359133 ]
  2. TOUSTER O, HARWELL SO: The isolation of L-arabitol from pentosuric urine. J Biol Chem. 1958 Feb;230(2):1031-41. [13525419 ]

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