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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2021-09-14 15:19:01 UTC
HMDB IDHMDB0002453
Secondary Accession Numbers
  • HMDB02453
Metabolite Identification
Common Name4-Deoxythreonic acid
Description4-Deoxythreonic acid, also known as 4-deoxythreonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 4-Deoxythreonic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-deoxythreonic acid a potential biomarker for the consumption of these foods. 4-Deoxythreonic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Deoxythreonic acid.
Structure
Data?1582752250
Synonyms
ValueSource
4-DeoxythreonateGenerator
(+/-)-erythro-2,3-dihydroxybutyrateHMDB
(+/-)-erythro-2,3-dihydroxybutyric acidHMDB
(2R,3S)-Rel-2,3-dihydroxy--butanoateHMDB
(2R,3S)-Rel-2,3-dihydroxy--butanoic acidHMDB
(R*,s*)-2,3-dihydroxybutanoateHMDB
(R*,s*)-2,3-dihydroxybutanoic acidHMDB
2,3-threo-DihydroxybutyrateHMDB
2,3-threo-Dihydroxybutyric acidHMDB
4-Deoxy-threonateHMDB
4-Deoxy-threonic acidHMDB
erythro-2,3-DihydroxybutyrateHMDB
erythro-2,3-Dihydroxybutyric acidHMDB
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name(2S,3R)-2,3-dihydroxybutanoic acid
Traditional Name4-deoxythreonic acid
CAS Registry Number5057-93-2
SMILES
C[C@@H](O)[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C4H8O4/c1-2(5)3(6)4(7)8/h2-3,5-6H,1H3,(H,7,8)/t2-,3+/m1/s1
InChI KeyLOUGYXZSURQALL-GBXIJSLDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Sugar acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility454 g/LALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS0.58ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.8 m³·mol⁻¹ChemAxon
Polarizability10.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available127.17331661259
DarkChem[M-H]-PredictedNot Available122.06231661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-Deoxythreonic acid,1TMS,#11173.5997https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,1TMS,#21195.1472https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,1TMS,#31112.6364https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,2TMS,#11283.2316https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,2TMS,#21246.7528https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,2TMS,#31249.7513https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,3TMS,#11361.8301https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,1TBDMS,#11435.4314https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,1TBDMS,#21453.3337https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,1TBDMS,#31342.4263https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,2TBDMS,#11743.5118https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,2TBDMS,#21690.7462https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,2TBDMS,#31693.1183https://arxiv.org/abs/1905.12712
4-Deoxythreonic acid,3TBDMS,#11996.4579https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-4f8b3914e68986e2fc762017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-7594000000-41795a8299b4ed9a75dc2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-3900000000-5fd7ebfcf6875e23274a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0umr-9500000000-6fef2d02f632a0eefd832016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-825548e71f4decf6fa072016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-9700000000-c98992a42c3b24d2b2992016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-9100000000-15421a37ae239a136cea2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-bdc0f45a587e25111ed42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9200000000-794a2a36a438372a84c32021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-9000000000-1db4f99bbccdd36ec8b02021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-488ae4d8cef018c0dfe12021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified12.3 (4.4-19.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified14.0 +/- 7.0 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified25.0 +/- 10.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified18.2 (5.6-23.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified307.674 +/- 224.458 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified442.222 +/- 291.319 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified765.086 +/- 469.712 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023007
KNApSAcK IDC00052154
Chemspider ID9139682
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6686
PubChem Compound10964471
PDB IDNot Available
ChEBI ID86391
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceSakai, Takashi; Nakamura, Toshiki; Fukuda, Katsuyoshi; Amano, Eiichiro; Utaka, Masanori; Takeda, Akira. Highly enantioselective reduction of ethyl 2-acyloxy-3-oxobutanoate with immobilized bakers' yeast. Bulletin of the Chemical Society of Japan (1986), 59(10), 3185-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chamberlin BA, Sweeley CC: Metabolic profiles of urinary organic acids recovered from absorbent filter paper. Clin Chem. 1987 Apr;33(4):572-6. [PubMed:3829393 ]
  2. Tuchman M, Bowers LD, Fregien KD, Crippin PJ, Krivit W: Capillary gas chromatographic separation of urinary organic acids. Retention indices of 101 urinary acids on a 5% phenylmethyl silicone capillary column. J Chromatogr Sci. 1984 May;22(5):198-202. [PubMed:6725493 ]
  3. Kassel DB, Martin M, Schall W, Sweeley CC: Urinary metabolites of L-threonine in type 1 diabetes determined by combined gas chromatography/chemical ionization mass spectrometry. Biomed Environ Mass Spectrom. 1986 Oct;13(10):535-40. [PubMed:2947647 ]
  4. Maeda K, Shiraishi S, Sakamoto N, Ohki T, Hosoi M, Ohta K, Yamanaka N: Identification of Escherichia coli by detection of hydroquinone and uracil in the urine system. J Chromatogr. 1985 Nov 29;345(1):11-8. [PubMed:3910670 ]