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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-05-24 01:32:05 UTC
HMDB IDHMDB0000498
Secondary Accession Numbers
  • HMDB00498
Metabolite Identification
Common Name4-Deoxyerythronic acid
Description4-Deoxyerythronic acid is a normal organic acid present in human biofluids (PMIDs 2338430, 3829393, 3525594, 14708889, 1560100, 6725493), derived presumably from L-threonine. (PMID 2947647 ) It has been associated with uremia (PMID 1149237 ) and diabetes mellitus type 1. (PMID 2947647 ).
Structure
Data?1558661525
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

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Polarizability10.74 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-4f8b3914e68986e2fc76JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-7594000000-41795a8299b4ed9a75dcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-4900000000-e93ff8f7aad0f2c8fdeaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9600000000-db7b2d4f0f4a450600e4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-c6f2a60b94ceef71fa3aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-9700000000-1e769b015c5e815e5fd1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-9200000000-320d571457b8c5b1a0acJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-222ebdab55908e04bc53JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified5.0 +/- 3.0 umol/mmol creatinineAdult (>18 years old)BothNormal
      • Geigy Scientific ...
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB 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
    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 ]