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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:18:55 UTC
HMDB IDHMDB0000498
Secondary Accession Numbers
  • HMDB00498
Metabolite Identification
Common Name4-Deoxyerythronic acid
Description4-Deoxyerythronic acid, also known as 2,3-dihydroxybutanoic acid, 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-Deoxyerythronic acid exists in all living organisms, ranging from bacteria to humans. 4-Deoxyerythronic 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-deoxyerythronic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Deoxyerythronic acid.
Structure
Data?1582752135
Synonyms
ValueSource
4-DeoxyerythronateGenerator
(+/-)-erythro-2,3-dihydroxybutyric acidHMDB
(R*,r*)-2,3-dihydroxy-butanoateHMDB
(R*,r*)-2,3-dihydroxy-butanoic acidHMDB
(R*,r*)-2,3-dihydroxybutanoateHMDB
(R*,r*)-2,3-dihydroxybutanoic acidHMDB
(R*,s*)-2,3-dihydroxybutanoateHMDB
(R*,s*)-2,3-dihydroxybutanoic acidHMDB
2,3-Dihydroxybutanoic acidHMDB
2,3-Erythro-dihydroxybutyrateHMDB
2,3-Erythro-dihydroxybutyric acidHMDB
4-Deoxy-erythronateHMDB
4-Deoxy-erythronic acidHMDB
4-Deoxytetronic acidHMDB
Erythro-2,3-dihydroxybutyric acidHMDB
(2R,3R)-2,3-DihydroxybutanoateHMDB
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name(2R,3R)-2,3-dihydroxybutanoic acid
Traditional Name4-deoxyerythronic acid
CAS Registry Number759-06-8
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-PWNYCUMCSA-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 DescriptorsNot Available
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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility454 g/LALOGPS
logP10(-1.2) g/LALOGPS
logP10(-1.1) g/LChemAxon
logS10(0.58) g/LALOGPS
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
Polarizability10.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.28331661259
DarkChem[M-H]-121.61131661259
AllCCS[M+H]+130.68732859911
AllCCS[M-H]-122.09232859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Deoxyerythronic acid,1TMS,#1C[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O1173.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TMS,#2C[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O1195.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TMS,#3C[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C1112.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TMS,#1C[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1283.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TMS,#2C[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1246.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TMS,#3C[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1249.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,3TMS,#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 polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TBDMS,#1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O1435.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TBDMS,#2C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1453.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TBDMS,#3C[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1342.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,3TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxyerythronic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-4f8b3914e68986e2fc762017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxyerythronic acid GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-7594000000-41795a8299b4ed9a75dc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxyerythronic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxyerythronic 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-Deoxyerythronic acid 10V, Positive-QTOFsplash10-0uk9-4900000000-e93ff8f7aad0f2c8fdea2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Positive-QTOFsplash10-0udr-9600000000-db7b2d4f0f4a450600e42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Positive-QTOFsplash10-0a4r-9000000000-c6f2a60b94ceef71fa3a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 10V, Negative-QTOFsplash10-016r-9700000000-1e769b015c5e815e5fd12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Negative-QTOFsplash10-05di-9200000000-320d571457b8c5b1a0ac2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Negative-QTOFsplash10-0ab9-9000000000-222ebdab55908e04bc532015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 10V, Negative-QTOFsplash10-00or-9800000000-2fbe96770b983d31a58d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Negative-QTOFsplash10-004l-9000000000-a0881fec62969be92bad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Negative-QTOFsplash10-0a4l-9000000000-16140d690957c073bf982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 10V, Positive-QTOFsplash10-0002-9200000000-794a2a36a438372a84c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Positive-QTOFsplash10-0a4j-9000000000-1db4f99bbccdd36ec8b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Positive-QTOFsplash10-0002-9000000000-488ae4d8cef018c0dfe12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified5.0 +/- 3.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022077
KNApSAcK IDNot Available
Chemspider ID17215960
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5484
PubChem Compound13120901
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceOwen, L. N. Oxygenation of crotonaldehyde. Journal of the Chemical Society (1943), 563-8.
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. Bultitude FW, Newham SJ: Identification of some abnormal metabolites in plasma from uremic subjects. Clin Chem. 1975 Aug;21(9):1329-34. [PubMed:1149237 ]