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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:02 UTC
HMDB IDHMDB00613
Secondary Accession NumbersNone
Metabolite Identification
Common NameErythronic acid
DescriptionErythronic acid is a sugar component of aqueous humour (eye). It may be derived from glycated proteins or from degradation of ascorbic acid. Erythronic acid is a normal organic acid present in a healthy adult and pediatric population. It has been found in urine, plasma, CSF and synovial fluid. (PMID: 14708889 , 8087979 , 8376520 , 10420182 ). Erythronic acid is formed when N-Acetyl-D-glucosamine (GlcNAc) is oxidised. GlcNAc is a constituent of hyaluronic acid (HA), a polysaccharide consisting of alternating units of Glucuronic acid and GlcNAc, present as an aqueous solution in synovial fluid. In synovial fluid of patients suffering from rheumatoid arthritis, HA is thought to be degraded either by radicals generated by Fenton chemistry (Fe2+/H2O2) or by NaOCl generated by myeloperoxidase. (PMID: 10614067 ).
Structure
Thumb
Synonyms
ValueSource
(R*,r*)-2,3,4-trihydroxy-butanoateHMDB
(R*,r*)-2,3,4-trihydroxy-butanoic acidHMDB
2,3,4-TrihydroxybutanoateHMDB
2,3,4-Trihydroxybutanoic acidHMDB
erythro-2,3,4-TrihydroxybutyrateHMDB
erythro-2,3,4-Trihydroxybutyric acidHMDB
ErythronateHMDB
Chemical FormulaC4H8O5
Average Molecular Weight136.1033
Monoisotopic Molecular Weight136.037173366
IUPAC Name(2R,3R)-2,3,4-trihydroxybutanoic acid
Traditional Nameerythronic acid
CAS Registry Number13752-84-6
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-PWNYCUMCSA-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 Point100 - 102 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
Polarizability11.68 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gc3-1980000000-3bdd6daf86a88d7ca9d8View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<5 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.0 +/- 5.0 uMAdult (>18 years old)Not SpecifiedNormal 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 Quantified17.9 (7.1-49.7) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified18.8 (11.9-36.2) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified8.5 (5.5-22.2) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified6.0 (3.9-17.6) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified109.0 +/- 19.0 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified20.0 +/- 8.0 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 IDFDB022143
KNApSAcK IDNot Available
Chemspider ID2061231
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00613
Metagene LinkHMDB00613
METLIN ID5586
PubChem Compound2781043
PDB IDNot Available
ChEBI ID37655
References
Synthesis ReferenceHeikkila, Heikki; Alen, Raimo; Kauko, Siru; Lindroos, Mirja; Nurmi, Juha; Sarmala, Paivi; Tylli, Matti. Method for producing xylitol and erythritol from arabinoxylan-containing materials. Eur. Pat. Appl. (2000), 9 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [14708889 ]
  2. 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 ]
  3. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [8412012 ]
  4. Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10. [8376520 ]
  5. 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 ]
  6. Jahn M, Baynes JW, Spiteller G: The reaction of hyaluronic acid and its monomers, glucuronic acid and N-acetylglucosamine, with reactive oxygen species. Carbohydr Res. 1999 Oct 15;321(3-4):228-34. [10614067 ]