| Common Name |
(S)-3,4-Dihydroxybutyric acid
| Description |
3,4-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 adlits 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(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 Formlia |
C4H8O4
| Average Molecliar Weight |
120.1039
| Monoisotopic Molecliar Weight |
120.042258744
| IUPAC Name |
3,4-dihydroxybutanoic acid
| Traditional Name |
3,4-dihydroxybutanoic acid
| CAS Registry Number |
51267-44-8
| 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 Key |
DZAIOXUZHHTJKN-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Hydroxy acids and derivatives
| Direct Parent |
Beta hydroxy acids and derivatives
| Alternative Parents |
Short-chain hydroxy acids and derivatives
Fatty acids and conjugates
Secondary alcohols
1,2-diols
Monocarboxylic acids and derivatives
Carboxylic acids
Primary alcohols
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
omega-hydroxy fatty acid (CHEBI:86371 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility832.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.01 m3·mol-1ChemAxon
Polarizability10.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0udr-5900000000-87e855dfa4a5229ec106View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0gw0-9300000000-88020d54d9b37645b873View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0a4u-9000000000-d0c64e75e2e9de34f683View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-014i-7900000000-6aec80cde1bf2e0bca19View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0pxr-9300000000-93d09801aa0c902a4e8fView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0a4l-9000000000-d765ea0631d195240881View in MoNA
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Blood
Cerebrospinal Fluid (CSF)
Feces
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified18.0 (0.0-54.0) uMAdlit (>18 years old)BothNormal
8412012
details
Cerebrospinal Fluid (CSF)Detected and Quantified15.0 +/- 15.0 uMAdlit (>18 years old)BothNormal
8412012
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
20669995
details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
22411374
details
UrineDetected but not Quantified Adlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified21.2 (9.3-47.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal
8087979
details
UrineDetected and Quantified23.9 (12.4-31.8) umol/mmol creatinineInfant (0-1 year old)BothNormal
8087979
details
UrineDetected and Quantified10.2 (6.4-16.7) umol/mmol creatinineChildren (1-13 years old)BothNormal
8087979
details
UrineDetected and Quantified8.3 (4.8-22.4) umol/mmol creatinineAdolescent (13-18 years old)BothNormal
8087979
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 creatinineAdlit (>18 years old)BothNormal
Geigy Scientific …
details
UrineDetected and Quantified34.9 (12.5 – 57.2) umol/mmol creatinineAdlit (>18 years old)Not SpecifiedNormal
1167165
details
UrineDetected and Quantified42.2 (21.9-56.1) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified98.0 (30.0-166.0) umol/mmol creatinineAdlit (>18 years old)BothSuccinic semialdehyde dehydrogenase deficiency
MetaGene
details
UrineDetected and Quantified137.5 (50.0-225.0) umol/mmol creatinineChildren (1-13 years old)Both4-Hydroxybutyric Aciduria
MetaGene
details
| Associated Disorders and Diseases |
| Disease References |
| Succinic semialdehyde dehydrogenase deficiency |
- MetaGene [Link]
- MetaGene [Link]
| Associated OMIM IDs |
271980 (Succinic semialdehyde dehydrogenase deficiency)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021961
| KNApSAcK ID |
Not Available
| Chemspider ID |
133026
| KEGG Compound ID |
Not Available
| BioCyc ID |
3-4DH3-4DHFLUORENE
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00337
| Metagene Link |
HMDB00337
| METLIN ID |
Not Available
| PubChem Compound |
150929
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Imipramine (hydrochloride)
References |
| Synthesis Reference |
Cho, 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 |
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
PMID: 8272405