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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 12:46:02 UTC
Update Date2021-09-14 15:44:37 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 ). 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, 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1160 g/LALOGPS
logP10(-2.5) g/LChemAxon
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.62331661259
DarkChem[M-H]-118.00131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-ThreitolOC[C@@H](O)[C@H](O)CO2515.9Standard polar33892256
D-ThreitolOC[C@@H](O)[C@H](O)CO1418.8Standard non polar33892256
D-ThreitolOC[C@@H](O)[C@H](O)CO1216.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Threitol,1TMS,isomer #1C[Si](C)(C)OC[C@@H](O)[C@H](O)CO1315.9Semi standard non polar33892256
D-Threitol,1TMS,isomer #2C[Si](C)(C)O[C@H](CO)[C@H](O)CO1280.6Semi standard non polar33892256
D-Threitol,2TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)CO1385.4Semi standard non polar33892256
D-Threitol,2TMS,isomer #2C[Si](C)(C)OC[C@@H](O)[C@@H](CO)O[Si](C)(C)C1381.1Semi standard non polar33892256
D-Threitol,2TMS,isomer #3C[Si](C)(C)OC[C@@H](O)[C@H](O)CO[Si](C)(C)C1408.6Semi standard non polar33892256
D-Threitol,2TMS,isomer #4C[Si](C)(C)O[C@H](CO)[C@@H](CO)O[Si](C)(C)C1356.6Semi standard non polar33892256
D-Threitol,3TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1438.8Semi standard non polar33892256
D-Threitol,3TMS,isomer #2C[Si](C)(C)OC[C@@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C1455.0Semi standard non polar33892256
D-Threitol,4TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C1506.8Semi standard non polar33892256
D-Threitol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)CO1554.4Semi standard non polar33892256
D-Threitol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)CO1531.6Semi standard non polar33892256
D-Threitol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO1812.0Semi standard non polar33892256
D-Threitol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C1817.9Semi standard non polar33892256
D-Threitol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C1818.6Semi standard non polar33892256
D-Threitol,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H](CO)[C@@H](CO)O[Si](C)(C)C(C)(C)C1832.0Semi standard non polar33892256
D-Threitol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2119.1Semi standard non polar33892256
D-Threitol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2097.0Semi standard non polar33892256
D-Threitol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2338.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - D-Threitol GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gba-0930000000-e0204c8d02428c3e37702014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Threitol EI-B (Non-derivatized)splash10-0gba-0960000000-d9fd44a0ca03aa2b2c7d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Threitol GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-e0204c8d02428c3e37702017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Threitol GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-43c8af225d82ebe7adcc2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Threitol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-8f6f577c436c69d844422017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Threitol GC-MS (4 TMS) - 70eV, Positivesplash10-0ab9-7249000000-2b2a68afd8e4a9b09f962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Threitol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3ac2b797c104b943b1d72018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Threitol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-05tr-9500000000-c66e9c2cdca98e1a30732018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Threitol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0006-9000000000-8c8289ff9dce6ace80fb2018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Threitol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-9a74ea83fa64739762c72018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Threitol 20V, Negative-QTOFsplash10-0ab9-9000000000-34ad3cd7ef2c53acc8282021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Threitol 10V, Negative-QTOFsplash10-0abi-9000000000-d8dd8f85d51c2fc749d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Threitol 40V, Negative-QTOFsplash10-052f-9000000000-6484e77778aff48219572021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 10V, Positive-QTOFsplash10-00di-2900000000-b21b0229b3cca7a445e12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 20V, Positive-QTOFsplash10-03k9-9500000000-793c9703aa07422f10142016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 40V, Positive-QTOFsplash10-01pd-9000000000-c17f1bba91d64dbd9f412016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 10V, Negative-QTOFsplash10-00di-7900000000-12421f1c391587323fb62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 20V, Negative-QTOFsplash10-05fr-9400000000-45979a06d5c9cf0240d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 40V, Negative-QTOFsplash10-0a4l-9000000000-e4d3d8da2791448160162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 10V, Positive-QTOFsplash10-000i-9100000000-742e9e4308373a8d5b172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 20V, Positive-QTOFsplash10-03dl-9000000000-7af74ca2560605f4e6d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 40V, Positive-QTOFsplash10-0006-9000000000-9c835b7fd9ca2f9a74a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 10V, Negative-QTOFsplash10-0fe0-9200000000-5696f87e798d441fc0492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 20V, Negative-QTOFsplash10-0a4i-9000000000-98bfc31aa7d0786684e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Threitol 40V, Negative-QTOFsplash10-0a4i-9000000000-588ee6697087d42604222021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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 QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
MarkerDB IDMDB00000441
Good Scents IDrw1242041
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. 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 ]
  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. 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 ]