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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:35 UTC
HMDB IDHMDB00360
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,4-Dihydroxybutanoic acid
Description2,4-Dihydroxybutanoic acid or 3-Deoxytetronic acid is usually absent in normal human urine extracts or in only trace constituents in neonates. (PMID 1192581 ) However, various cases of succinic semialdehyde dehydrogenase deficiency have shown consistently increased amounts of this metabolite. (PMID 3126356 ).
Structure
Thumb
Synonyms
ValueSource
2,4-Dihydroxy-butyrateHMDB
2,4-Dihydroxy-butyric acidHMDB
2,4-DihydroxybutanoateHMDB
2,4-DihydroxybutyrateHMDB
2,4-Dihydroxybutyric acidHMDB
3-DeoxytetronateHMDB
3-Deoxytetronic acidHMDB
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name2,4-dihydroxybutanoic acid
Traditional Name2,4-dihydroxybutyric acid
CAS Registry Number1518-62-3
SMILES
OCCC(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O4/c5-2-1-3(6)4(7)8/h3,5-6H,1-2H2,(H,7,8)
InChI KeyInChIKey=UFYGCFHQAXXBCF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility700.0 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.5ChemAxon
logS0.77ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.25 m3·mol-1ChemAxon
Polarizability10.93 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 (3 TMS)splash10-0udi-1910000000-557fbb6f2bb47435373cView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.0-7.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified84 uMChildren (1-13 years old)BothNormal details
UrineDetected and Quantified1.0 (0.3-1.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.0 +/- 2.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified7.8 (1.9-18.4) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified8.1 (4.9-19.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified5.4 (2.5-7.3) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified4.0 (1.9-15.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified4.3 (3.3-1.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
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 IDFDB021980
KNApSAcK IDNot Available
Chemspider ID167259
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00360
Metagene LinkHMDB00360
METLIN ID5349
PubChem Compound192742
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceRadej, Z.; Kristofova, Z. Hydroxy acid and lactone fraction of black liquor. Papir a Celuloza (1964), 19(6), 152-3.
Material Safety Data Sheet (MSDS)Not Available
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. Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [1192581 ]
  3. Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75. [3126356 ]