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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:39:18 UTC
HMDB IDHMDB0000360
Secondary Accession Numbers
  • HMDB00360
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-Dihydroxybutyric acidChEBI
2,4-DihydroxybutyrateGenerator
2,4-DihydroxybutanoateGenerator
2,4-Dihydroxy-butyrateHMDB
2,4-Dihydroxy-butyric 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 KeyUFYGCFHQAXXBCF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy acids and derivatives
Direct ParentShort-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.25 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
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
GC-MSGC-MS Spectrum - GC-MSsplash10-0udi-1910000000-557fbb6f2bb47435373cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-7900000000-3d1731c289c7fe265549View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-9200000000-24bce363159074dbdc00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-aa7e1aa11c5f98b28b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9700000000-94ff900476f71827e9aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-9100000000-ea29f47da5ae8add20c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9000000000-bc3515dda55b1fc1dcd2View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 Quantified Adult (>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
METLIN ID5349
PubChem Compound192742
PDB IDNot Available
ChEBI ID86348
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. [PubMed: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. [PubMed: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. [PubMed:3126356 ]