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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:39:09 UTC
HMDB IDHMDB0000337
Secondary Accession Numbers
  • HMDB00337
  • HMDB06118
Metabolite Identification
Common Name(S)-3,4-Dihydroxybutyric acid
Description3,4-Dihydroxybutyric acid is a normal human urinary metabolite that is excreted in increased concentration in patients with succinic semialdehyde dehydrogenase (SSADH) deficiency. (PMID 12127325 ) Normal adults excrete 0.37 +/- 0.15 (SD) mmoles of 3,4-dihydroxybutyrate per 24 hr. The compound is also detectable in blood. The renal clearance of this compound is roughly equal that of creatinine.
Structure
Thumb
Synonyms
ValueSource
(S)-3,4-Dihydroxy-butyric acidHMDB
(S)-3,4-DihydroxybutanoateHMDB
(S)-3,4-Dihydroxybutanoic acidHMDB
2-DeoxytetronateHMDB
2-Deoxytetronic acidHMDB
3,4-DihydroxybutanoateHMDB
3,4-Dihydroxybutanoic acidHMDB
3,4-Dihydroxybutanoic acid, (S)-isomerMeSH
3,4-Dihydroxybutanoic acid, monosodium saltMeSH
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name3,4-dihydroxybutanoic acid
Traditional Name3,4-dihydroxybutanoic acid
CAS Registry Number51267-44-8
SMILES
OCC(O)CC(O)=O
InChI Identifier
InChI=1S/C4H8O4/c5-2-3(6)1-4(7)8/h3,5-6H,1-2H2,(H,7,8)
InChI KeyDZAIOXUZHHTJKN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Fatty acid
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • 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 Solubility832 g/LALOGPS
logP-1.5ALOGPS
logP-1.4ChemAxon
logS0.84ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.01 m³·mol⁻¹ChemAxon
Polarizability10.91 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-EI-TOFsplash10-0012-0910000000-4054231c9c4cffa8a3c9View 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, Positivesplash10-0udr-5900000000-87e855dfa4a5229ec106View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gw0-9300000000-88020d54d9b37645b873View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9000000000-d0c64e75e2e9de34f683View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-7900000000-6aec80cde1bf2e0bca19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pxr-9300000000-93d09801aa0c902a4e8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-d765ea0631d195240881View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified18.0 (0.0-54.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified15.0 +/- 15.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified21.2 (9.3-47.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified23.9 (12.4-31.8) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified10.2 (6.4-16.7) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified8.3 (4.8-22.4) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified73.0 +/- 24.0 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified8.0 +/- 3.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified34.9 (12.5 - 57.2) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified42.2 (21.9-56.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified98.0 (30.0-166.0) umol/mmol creatinineAdult (>18 years old)BothSuccinic semialdehyde dehydrogenase deficiency details
UrineDetected and Quantified137.5 (50.0-225.0) umol/mmol creatinineChildren (1-13 years old)Both4-Hydroxybutyric Aciduria details
Associated Disorders and Diseases
Disease References
Succinic semialdehyde dehydrogenase deficiency
    MetaGeneMetaGene
Associated OMIM IDs
  • 271980 (Succinic semialdehyde dehydrogenase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021961
KNApSAcK IDNot Available
Chemspider ID133026
KEGG Compound IDNot Available
BioCyc ID3-4DH3-4DHFLUORENE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150929
PDB IDNot Available
ChEBI ID86371
References
Synthesis ReferenceCho, Yik-haeng; Chun, Jongpil; Park, Youngmi; Roh, Kyoungrok; Yu, Hosung; Hwang, Daeil. Process for preparing optically pure (S)-3,4-dihydroxybutyric acid derivatives. PCT Int. Appl. (2000), 29 pp.
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. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  3. Nakajima MO, Etoh Y, Yanai M, Kawamura R, Kaneko K, Aoyagi K, Koiso K: [Novel renal function marker, ATP--establishing the normal range, cases of anti-tumor drags administration for urinary-track tumor, diabetic diseases and a newborn baby]. Rinsho Byori. 2002 May;50(5):513-8. [PubMed:12078051 ]
  4. Fell V, Lee CR, Pollitt RJ: The occurrence of (S)-3,4-dihydroxybutyrate in human blood and urine. Biochem Med. 1975 May;13(1):40-5. [PubMed:1167165 ]
  5. Shinka T, Inoue Y, Ohse M, Ito A, Ohfu M, Hirose S, Kuhara T: Rapid and sensitive detection of urinary 4-hydroxybutyric acid and its related compounds by gas chromatography-mass spectrometry in a patient with succinic semialdehyde dehydrogenase deficiency. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 25;776(1):57-63. [PubMed:12127325 ]