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Showing metabocard for 4-Deoxythreonic acid (HMDB0002453)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2019-07-23 05:45:32 UTC
HMDB IDHMDB0002453
Secondary Accession Numbers
  • HMDB02453
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
Data?1563860732
MOLSDFPDBSMILESInChI
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
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
Polarizability10.72 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, Positivesplash10-0uk9-3900000000-5fd7ebfcf6875e23274aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0umr-9500000000-6fef2d02f632a0eefd83JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-825548e71f4decf6fa07JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-9700000000-c98992a42c3b24d2b299JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-9100000000-15421a37ae239a136ceaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-bdc0f45a587e25111ed4JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    		 details
    UrineDetected and Quantified12.3 (4.4-19.8) umol/mmol creatinineAdult (>18 years old)Both
    Normal    		 details
    UrineDetected but not Quantified Adult (>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
    UrineDetected but not Quantified Adult (>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
      • Mordechai, Hien, ...
    		 details
    UrineDetected and Quantified765.086 +/- 469.712 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    		 details
    UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
    Associated Disorders and Diseases
    Disease References
    Eosinophilic esophagitis
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB023007
    KNApSAcK IDNot Available
    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
    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. 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 ]
    2. 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 ]
    3. 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 ]
    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 ]