Showing metabocard for D-Threitol (LMDB00448)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:50:05 UTC
Update Date2016-07-20 21:01:09 UTC
LmdbLMDB00448
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Threitol
DescriptionD-Threitol can be regarded as the main end product of D-xylose metabolism in man. Threitol is a C4-polyol (tetritol); the total C4-polyol concentration of threitol decreases with age. Several inborn errors of metabolism with abnormal polyol concentrations in body fluids are known to date (such as pentosuria and galactosemia). Most of these defects can be diagnosed by the assessment of urinary concentrations of polyols. Several studies have revealed that urinary levels of some polyols may vary in diseases associated with carbohydrate metabolism derangements such as diabetes mellitus and uremia. The abnormal occurrence of various polyols in diseases with a specific enzyme deficiency such as pentosuria4 and galactosemias has also been reported. (PMID: 908147 , 16435188 , 14988808 , Analytical Sciences (1990), 6(5), 657-66.).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
D-Threo-tetritolChEBI
(-)-ThreitolHMDB
(R*,r*)-1,2,3,4-butanetetrolHMDB
ThreitHMDB
ThreitolHMDB, MeSH
Threitol, ((r*,r*)-(+-))-isomerMeSH, HMDB
Threitol, (R-(r*,r*))-isomerMeSH, HMDB
1,2,3,4-TetrahydroxybutaneHMDB
Chemical FormulaC4H10O4
Average Molecular Weight122.1198
Monoisotopic Molecular Weight122.057908808
IUPAC Name(2R,3R)-butane-1,2,3,4-tetrol
Traditional Name(-)-threitol
CAS Registry Number2418-52-2
SMILES
OC[C@@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1
InChI KeyUNXHWFMMPAWVPI-QWWZWVQMSA-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
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.5ChemAxon
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.48 m³·mol⁻¹ChemAxon
Polarizability11.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gba-0930000000-e0204c8d02428c3e3770Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gba-0960000000-d9fd44a0ca03aa2b2c7dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-e0204c8d02428c3e3770Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-43c8af225d82ebe7adccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-8f6f577c436c69d84442Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ab9-7249000000-2b2a68afd8e4a9b09f96Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05tr-9500000000-c66e9c2cdca98e1a3073Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-8c8289ff9dce6ace80fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9a74ea83fa64739762c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9000000000-34ad3cd7ef2c53acc828Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0abi-9000000000-d8dd8f85d51c2fc749d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-6484e77778aff4821957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-b21b0229b3cca7a445e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-9500000000-793c9703aa07422f1014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pd-9000000000-c17f1bba91d64dbd9f41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-7900000000-12421f1c391587323fb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9400000000-45979a06d5c9cf0240d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e4d3d8da279144816016Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-742e9e4308373a8d5b17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-7af74ca2560605f4e6d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-9c835b7fd9ca2f9a74a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fe0-9200000000-5696f87e798d441fc049Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-98bfc31aa7d0786684e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-588ee6697087d4260422Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3ac2b797c104b943b1d7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
DrugBank IDNot Available
HMDB IDHMDB0004136
FooDB IDFDB002261
Phenol Explorer IDNot Available
KNApSAcK IDC00034313
BiGG IDNot Available
BioCyc IDCPD-12825
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkThreitol
Chemspider ID147828
ChEBI ID48300
PubChem Compound ID169019
Kegg Compound IDC16884
YMDB IDNot Available
ECMDB IDM2MDB005437
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wamelink MM, Smith DE, Jakobs C, Verhoeven NM: Analysis of polyols in urine by liquid chromatography-tandem mass spectrometry: a useful tool for recognition of inborn errors affecting polyol metabolism. J Inherit Metab Dis. 2005;28(6):951-63. [16435188 ]
  2. Pitkanen E: The conversion of D-xylose into D-threitol in patients without liver disease and in patients with portal liver cirrhosis. Clin Chim Acta. 1977 Oct 1;80(1):49-54. [908147 ]
  3. 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 ]