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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:17:12 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
Thumb
Synonyms
ValueSource
(+/-)-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-DeoxyerythronateHMDB
4-Deoxytetronic acidHMDB
erythro-2,3-Dihydroxybutyric acidHMDB
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
DescriptionThis compound belongs to the class of chemical entities known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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:

  Subcellular:

  Biofluid and excreta:

Source:

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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-4f8b3914e68986e2fc76View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-7594000000-41795a8299b4ed9a75dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-4900000000-e93ff8f7aad0f2c8fdeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9600000000-db7b2d4f0f4a450600e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-c6f2a60b94ceef71fa3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-9700000000-1e769b015c5e815e5fd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-9200000000-320d571457b8c5b1a0acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-222ebdab55908e04bc53View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite 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 ]