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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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

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 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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.17331661259
DarkChem[M-H]-122.06231661259
DeepCCS[M+H]+124.25430932474
DeepCCS[M-H]-120.55130932474
DeepCCS[M-2H]-157.90330932474
DeepCCS[M+Na]+133.31530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Deoxythreonic acidC[C@@H](O)[C@H](O)C(O)=O2364.8Standard polar33892256
4-Deoxythreonic acidC[C@@H](O)[C@H](O)C(O)=O1077.2Standard non polar33892256
4-Deoxythreonic acidC[C@@H](O)[C@H](O)C(O)=O1120.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Deoxythreonic acid,1TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H](O)C(=O)O1173.6Semi standard non polar33892256
4-Deoxythreonic acid,1TMS,isomer #2C[C@@H](O)[C@H](O[Si](C)(C)C)C(=O)O1195.1Semi standard non polar33892256
4-Deoxythreonic acid,1TMS,isomer #3C[C@@H](O)[C@H](O)C(=O)O[Si](C)(C)C1112.6Semi standard non polar33892256
4-Deoxythreonic acid,2TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=O)O1283.2Semi standard non polar33892256
4-Deoxythreonic acid,2TMS,isomer #2C[C@@H](O[Si](C)(C)C)[C@H](O)C(=O)O[Si](C)(C)C1246.8Semi standard non polar33892256
4-Deoxythreonic acid,2TMS,isomer #3C[C@@H](O)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1249.8Semi standard non polar33892256
4-Deoxythreonic acid,3TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1361.8Semi standard non polar33892256
4-Deoxythreonic acid,1TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(=O)O1435.4Semi standard non polar33892256
4-Deoxythreonic acid,1TBDMS,isomer #2C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O1453.3Semi standard non polar33892256
4-Deoxythreonic acid,1TBDMS,isomer #3C[C@@H](O)[C@H](O)C(=O)O[Si](C)(C)C(C)(C)C1342.4Semi standard non polar33892256
4-Deoxythreonic acid,2TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O1743.5Semi standard non polar33892256
4-Deoxythreonic acid,2TBDMS,isomer #2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(=O)O[Si](C)(C)C(C)(C)C1690.7Semi standard non polar33892256
4-Deoxythreonic acid,2TBDMS,isomer #3C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1693.1Semi standard non polar33892256
4-Deoxythreonic acid,3TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1996.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxythreonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-4f8b3914e68986e2fc762017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxythreonic acid GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-7594000000-41795a8299b4ed9a75dc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxythreonic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 10V, Positive-QTOFsplash10-0uk9-3900000000-5fd7ebfcf6875e23274a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 20V, Positive-QTOFsplash10-0umr-9500000000-6fef2d02f632a0eefd832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 40V, Positive-QTOFsplash10-0a4r-9000000000-825548e71f4decf6fa072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 10V, Negative-QTOFsplash10-016r-9700000000-c98992a42c3b24d2b2992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 20V, Negative-QTOFsplash10-05di-9100000000-15421a37ae239a136cea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 40V, Negative-QTOFsplash10-0ab9-9000000000-bdc0f45a587e25111ed42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 10V, Negative-QTOFsplash10-00or-9800000000-2fbe96770b983d31a58d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 20V, Negative-QTOFsplash10-004l-9000000000-a0881fec62969be92bad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 40V, Negative-QTOFsplash10-0a4l-9000000000-16140d690957c073bf982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 10V, Positive-QTOFsplash10-0002-9200000000-794a2a36a438372a84c32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 20V, Positive-QTOFsplash10-0a4j-9000000000-1db4f99bbccdd36ec8b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxythreonic acid 40V, Positive-QTOFsplash10-0002-9000000000-488ae4d8cef018c0dfe12021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView 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
    • Analysis of 30 no...
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
    • Analysis of 30 no...
details
UrineDetected and Quantified765.086 +/- 469.712 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
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
Good Scents 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. 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 ]
  2. 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 ]
  3. 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 ]
  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 ]