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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 12:46:02 UTC

Update Date

2021-09-14 15:44:37 UTC

HMDB ID

HMDB0004136

Secondary Accession Numbers

HMDB04136

Metabolite Identification

Common Name

D-Threitol

Description

D-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
D-Threo-tetritol	ChEBI
(-)-Threitol	HMDB
(R,r)-1,2,3,4-butanetetrol	HMDB
Threit	HMDB
Threitol	HMDB, MeSH
Threitol, ((r,r)-(+-))-isomer	MeSH, HMDB
Threitol, (R-(r,r))-isomer	MeSH, HMDB
1,2,3,4-Tetrahydroxybutane	HMDB

Chemical Formula

C₄H₁₀O₄

Average Molecular Weight

122.1198

Monoisotopic Molecular Weight

122.057908808

IUPAC Name

(2R,3R)-butane-1,2,3,4-tetrol

Traditional Name

(-)-threitol

CAS Registry Number

2418-52-2

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 Key

UNXHWFMMPAWVPI-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

threitol (CHEBI:48300 )

Ontology

Not Available

Exogenous (HMDB: HMDB0094689)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1160 g/L	ALOGPS
logP	-2.5	ChemAxon
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.48 m³·mol⁻¹	ChemAxon
Polarizability	11.66 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.623	31661259
DarkChem	[M-H]-	118.001	31661259
DeepCCS	[M+H]+	125.456	30932474
DeepCCS	[M-H]-	122.346	30932474
DeepCCS	[M-2H]-	159.106	30932474
DeepCCS	[M+Na]+	134.484	30932474
AllCCS	[M+H]+	130.5	32859911
AllCCS	[M+H-H2O]+	126.4	32859911
AllCCS	[M+NH4]+	134.4	32859911
AllCCS	[M+Na]+	135.5	32859911
AllCCS	[M-H]-	122.9	32859911
AllCCS	[M+Na-2H]-	126.1	32859911
AllCCS	[M+HCOO]-	129.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Threitol	OC[C@@H](O)[C@H](O)CO	2515.9	Standard polar	33892256
D-Threitol	OC[C@@H](O)[C@H](O)CO	1418.8	Standard non polar	33892256
D-Threitol	OC[C@@H](O)[C@H](O)CO	1216.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Threitol,1TMS,isomer #1	C[Si](C)(C)OC[C@@H](O)[C@H](O)CO	1315.9	Semi standard non polar	33892256
D-Threitol,1TMS,isomer #2	C[Si](C)(C)O[C@H](CO)[C@H](O)CO	1280.6	Semi standard non polar	33892256
D-Threitol,2TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)CO	1385.4	Semi standard non polar	33892256
D-Threitol,2TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1381.1	Semi standard non polar	33892256
D-Threitol,2TMS,isomer #3	C[Si](C)(C)OC[C@@H](O)[C@H](O)CO[Si](C)(C)C	1408.6	Semi standard non polar	33892256
D-Threitol,2TMS,isomer #4	C[Si](C)(C)O[C@H](CO)[C@@H](CO)O[Si](C)(C)C	1356.6	Semi standard non polar	33892256
D-Threitol,3TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1438.8	Semi standard non polar	33892256
D-Threitol,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	1455.0	Semi standard non polar	33892256
D-Threitol,4TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	1506.8	Semi standard non polar	33892256
D-Threitol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)CO	1554.4	Semi standard non polar	33892256
D-Threitol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)CO	1531.6	Semi standard non polar	33892256
D-Threitol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	1812.0	Semi standard non polar	33892256
D-Threitol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	1817.9	Semi standard non polar	33892256
D-Threitol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C	1818.6	Semi standard non polar	33892256
D-Threitol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@@H](CO)O[Si](C)(C)C(C)(C)C	1832.0	Semi standard non polar	33892256
D-Threitol,3TBDMS,isomer #1	CC(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)C	2119.1	Semi standard non polar	33892256
D-Threitol,3TBDMS,isomer #2	CC(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)C	2097.0	Semi standard non polar	33892256
D-Threitol,4TBDMS,isomer #1	CC(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)C	2338.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - D-Threitol GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0gba-0930000000-e0204c8d02428c3e3770	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Threitol EI-B (Non-derivatized)	splash10-0gba-0960000000-d9fd44a0ca03aa2b2c7d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Threitol GC-EI-TOF (Non-derivatized)	splash10-0gba-0930000000-e0204c8d02428c3e3770	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Threitol GC-EI-TOF (Non-derivatized)	splash10-0gba-0930000000-43c8af225d82ebe7adcc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Threitol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9000000000-8f6f577c436c69d84442	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Threitol GC-MS (4 TMS) - 70eV, Positive	splash10-0ab9-7249000000-2b2a68afd8e4a9b09f96	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Threitol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01ox-9000000000-3ac2b797c104b943b1d7	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Threitol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-05tr-9500000000-c66e9c2cdca98e1a3073	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Threitol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-8c8289ff9dce6ace80fb	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Threitol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-9a74ea83fa64739762c7	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Threitol 20V, Negative-QTOF	splash10-0ab9-9000000000-34ad3cd7ef2c53acc828	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Threitol 10V, Negative-QTOF	splash10-0abi-9000000000-d8dd8f85d51c2fc749d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Threitol 40V, Negative-QTOF	splash10-052f-9000000000-6484e77778aff4821957	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 10V, Positive-QTOF	splash10-00di-2900000000-b21b0229b3cca7a445e1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 20V, Positive-QTOF	splash10-03k9-9500000000-793c9703aa07422f1014	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 40V, Positive-QTOF	splash10-01pd-9000000000-c17f1bba91d64dbd9f41	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 10V, Negative-QTOF	splash10-00di-7900000000-12421f1c391587323fb6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 20V, Negative-QTOF	splash10-05fr-9400000000-45979a06d5c9cf0240d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 40V, Negative-QTOF	splash10-0a4l-9000000000-e4d3d8da279144816016	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 10V, Positive-QTOF	splash10-000i-9100000000-742e9e4308373a8d5b17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 20V, Positive-QTOF	splash10-03dl-9000000000-7af74ca2560605f4e6d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 40V, Positive-QTOF	splash10-0006-9000000000-9c835b7fd9ca2f9a74a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 10V, Negative-QTOF	splash10-0fe0-9200000000-5696f87e798d441fc049	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 20V, Negative-QTOF	splash10-0a4i-9000000000-98bfc31aa7d0786684e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Threitol 40V, Negative-QTOF	splash10-0a4i-9000000000-588ee6697087d4260422	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.5 (0.0-5.0) uM	Adolescent (13-18 years old)	Both	Normal	14988808	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	<2.620 uM	Adult (>18 years old)	Both	Normal	12675874	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0 - 7.0 uM	Adolescent (13-18 years old)	Both	Normal	14988808	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	10.0 (5.6-15.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	45.0 (7.0 - 83) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	14988808	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected and Quantified	19.3 (5.3-32.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	6.5 (5.0-8.0) uM	Adolescent (13-18 years old)	Both	Ribose-5-Phosphate Isomerase Deficiency	14988808	details
Blood	Detected and Quantified	8.115 +/- 7.541 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	29 - 67 uM	Adolescent (13-18 years old)	Both	Ribose-5-Phosphate Isomerase Deficiency	14988808	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cryptosporidium infection	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	55.0 (38.0 - 81.0) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Ribose-5-Phosphate Isomerase Deficiency	14988808	details

Associated Disorders and Diseases

Disease References

Uremia
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
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 ] 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
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)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Threitol

METLIN ID

Not Available

PubChem Compound

169019

PDB ID

Not Available

ChEBI ID

48300

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000441

Good Scents ID

rw1242041

References

Synthesis Reference

Synthesis 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

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 ]
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 ]
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 ]

Showing metabocard for D-Threitol (HMDB0004136)

MOL for HMDB0004136 (D-Threitol)

3D MOL for HMDB0004136 (D-Threitol)

3D SDF for HMDB0004136 (D-Threitol)

3D-SDF for HMDB0004136 (D-Threitol)

PDB for HMDB0004136 (D-Threitol)

3D PDB for HMDB0004136 (D-Threitol)

SMILES for HMDB0004136 (D-Threitol)

INCHI for HMDB0004136 (D-Threitol)

Structure for HMDB0004136 (D-Threitol)

3D Structure for HMDB0004136 (D-Threitol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra