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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 12:46:02 UTC
Update Date2020-02-26 21:24:59 UTC
HMDB IDHMDB0004136
Secondary Accession Numbers
  • HMDB04136
Metabolite Identification
Common NameD-Threitol
DescriptionD-Threitol can be regarded as the main end product of D-xylose metabolism in hummans. 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 pentosuria and galactosemia has also been reported (PMID: 908147 , 16435188 , 14988808 , Analytical Sciences (1990), 6(5), 657-66.). Moreover, D-Threitol is found to be associated with ribose-5-phosphate isomerase deficiency, which is also an inborn error of metabolism. Threitol in the urine is a biomarker for the consumption of apples and other fruits.
Structure
Data?1582752299
Synonyms
ValueSource
D-Threo-tetritolChEBI
(-)-ThreitolHMDB
(R*,r*)-1,2,3,4-butanetetrolHMDB
ThreitHMDB
ThreitolHMDB
Threitol, ((r*,r*)-(+-))-isomerHMDB
Threitol, (R-(r*,r*))-isomerHMDB
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1160 g/LALOGPS
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 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) (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
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
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
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
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.5 (0.0-5.0) uMAdolescent (13-18 years old)BothNormal details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified<2.620 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0 - 7.0 uMAdolescent (13-18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.0 (5.6-15.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified45.0 (7.0 - 83) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified19.3 (5.3-32.7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.5 (5.0-8.0) uMAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
BloodDetected and Quantified8.115 +/- 7.541 uMAdult (>18 years old)Both
Uremia
details
Cerebrospinal Fluid (CSF)Detected and Quantified29 - 67 uMAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Not SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected and Quantified55.0 (38.0 - 81.0) umol/mmol creatinineAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
Associated Disorders and Diseases
Disease References
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 ]
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 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 608611 (Ribose-5-phosphate isomerase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002261
KNApSAcK IDC00034313
Chemspider ID147828
KEGG Compound IDC16884
BioCyc IDCPD-12825
BiGG IDNot Available
Wikipedia LinkThreitol
METLIN IDNot Available
PubChem Compound169019
PDB IDNot Available
ChEBI ID48300
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSynthesis of the stereoisomeric 1,2:3,4-dioxidobutanes. Feit, Peter W. Chemische Berichte (1960), 93 116-27.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:908147 ]
  2. 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. [PubMed:16435188 ]
  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. [PubMed:14988808 ]