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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:35 UTC
HMDB IDHMDB00943
Secondary Accession NumbersNone
Metabolite Identification
Common NameThreonic acid
DescriptionThreonic acid is probably derived from glycated proteins or from degradation of ascorbic acid. It is a normal component is aqeous humour and blood (PMID 10420182 ). Threonic acid is a substrate of L-threonate 3-dehydrogenase [EC 1.1.1.129] in ascorbate and aldarate metabolism pathway (KEGG).
Structure
Thumb
Synonyms
ValueSource
(R*,s*)-2,3,4-trihydroxy-butanoateHMDB
(R*,s*)-2,3,4-trihydroxy-butanoic acidHMDB
threo-2,3,4-TrihydroxybutyrateHMDB
threo-2,3,4-Trihydroxybutyric acidHMDB
ThreonateHMDB
Chemical FormulaC4H8O5
Average Molecular Weight136.1033
Monoisotopic Molecular Weight136.037173366
IUPAC Name(2S,3R)-2,3,4-trihydroxybutanoic acid
Traditional Namethreonic acid
CAS Registry Number3909-12-4
SMILES
OC[C@@H](O)[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1
InChI KeyInChIKey=JPIJQSOTBSSVTP-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
  • Polyol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 Solubility53 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility488.0 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.1ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.35 m3·mol-1ChemAxon
Polarizability11.61 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kp-9400000000-65ee9acbf3bfc5e1217dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00l2-9100000000-530757fa85c48c04e4f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014j-9100000000-0598e87e111f68c2e5adView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified14.8 (8.6-36.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified63.0 +/- 21.0 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified88.928 +/- 40.543 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified10.0 +/- 7.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified20.8 (10.2 - 39.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified14.2 (4.2-36.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified13.4 (5.1-46.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.5 (2.1-13.6) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified3.1(1.7-13.7) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
gastric cancer
details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
superficial gastric cancer
details
UrineDetected and Quantified114.997 +/- 87.963 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer 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 IDFDB022331
KNApSAcK IDNot Available
Chemspider ID133224
KEGG Compound IDC01620
BioCyc IDNot Available
BiGG ID38497
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00943
Metagene LinkHMDB00943
METLIN ID5891
PubChem Compound151152
PDB IDNot Available
ChEBI ID49059
References
Synthesis ReferenceSong J Z; Huang D P; Tian S J; Sun Z P Determination of L-threonate in calcium L-threonate preparations by capillary electrophoresis with indirect UV detection. Electrophoresis (1999), 20(9), 1850-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  2. Chalmers RA, Lawson AM, Hauschildt S, Watts RW: The urinary excretion of glycollic acid and threonic acid by xylitol-infused patients and their relationship to the possible role of 'active glycoladehyde' in the transketolase reaction in vivo. Biochem Soc Trans. 1975;3(4):518-21. [1183712 ]
  3. Harding JJ, Hassett PC, Rixon KC, Bron AJ, Harvey DJ: Sugars including erythronic and threonic acids in human aqueous humour. Curr Eye Res. 1999 Aug;19(2):131-6. [10420182 ]
  4. Leveque N, Mac-Mary S, Muret P, Makki S, Aubin F, Kantelip JP, Heusele C, S S, Humbert P: Evaluation of a sunscreen photoprotective effect by ascorbic acid assessment in human dermis using microdialysis and gas chromatography mass spectrometry. Exp Dermatol. 2005 Mar;14(3):176-81. [15740589 ]
  5. Watts RW, Hauschildt S, Chalmers RA, Lawson AM: Metabolic investigations during xylitol infusion. Int Z Vitam Ernahrungsforsch Beih. 1976;15:216-25. [821885 ]