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Record Information
Version3.6
Creation Date2006-05-22 14:17:53 UTC
Update Date2016-02-11 01:05:40 UTC
HMDB IDHMDB02453
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Deoxythreonic acid
Description4-Deoxythreonic acid is a normally occurring carboxylic acid in human. (PMID: 3829393 , 6725493 ). Metabolic profiling of urinary organic acids from patients with juvenile-onset (Type 1) diabetes mellitus have revealed significantly elevated levels of 4-deoxythreonic acid. (PMID: 2947647 ). The normal urinary constituent 4-deoxythreonic acid was found to diminish in urine incubated with E. coli. (PMID: 3910670 ).
Structure
Thumb
Synonyms
ValueSource
(+/-)-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
4-DeoxythreonateHMDB
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 KeyInChIKey=LOUGYXZSURQALL-GBXIJSLDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Sugar acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility454.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.8 m3·mol-1ChemAxon
Polarizability10.72 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified12.3 (4.4-19.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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 IDFDB023007
KNApSAcK IDNot Available
Chemspider ID9139682
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02453
Metagene LinkHMDB02453
METLIN ID6686
PubChem Compound10964471
PDB IDNot Available
ChEBI 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. [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. [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. [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. [3910670 ]