| Common Name |
2,4-Dihydroxybutanoic acid
| Description |
2,4-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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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 Formlia |
C4H8O4
| Average Molecliar Weight |
120.1039
| Monoisotopic Molecliar Weight |
120.042258744
| IUPAC Name |
2,4-dihydroxybutanoic acid
| Traditional Name |
2,4-dihydroxybutyric acid
| CAS Registry Number |
1518-62-3
| 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 Key |
UFYGCFHQAXXBCF-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Hydroxy acids and derivatives
| Direct Parent |
Short-chain hydroxy acids and derivatives
| Alternative Parents |
Monosaccharides
Fatty acids and conjugates
Alpha hydroxy acids and derivatives
Secondary alcohols
Monocarboxylic acids and derivatives
Carboxylic acids
Primary alcohols
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
hydroxybutyric acid (CHEBI:86348 )
omega-hydroxy fatty acid (CHEBI:86348 )
Hydroxy fatty acids (LMFA01050385 )
| 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 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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (3 TMS)splash10-0udi-1910000000-557fbb6f2bb47435373cView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Blood
Cerebrospinal Fluid (CSF)
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified2.0 (0.0-7.0) uMAdlit (>18 years old)BothNormal
8412012
details
Cerebrospinal Fluid (CSF)Detected and Quantified84 uMChildren (1-13 years old)BothNormal
8412012
details
UrineDetected and Quantified1.0 (0.3-1.8) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
UrineDetected but not Quantified Adlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified2.0 +/- 2.0 umol/mmol creatinineAdlit (>18 years old)BothNormal
Geigy Scientific …
details
UrineDetected and Quantified7.8 (1.9-18.4) umol/mmol creatinineNewborn (0-30 days old)BothNormal
8087979
details
UrineDetected and Quantified8.1 (4.9-19.3) umol/mmol creatinineInfant (0-1 year old)BothNormal
8087979
details
UrineDetected and Quantified5.4 (2.5-7.3) umol/mmol creatinineChildren (1-13 years old)BothNormal
8087979
details
UrineDetected and Quantified4.0 (1.9-15.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal
8087979
details
UrineDetected and Quantified4.3 (3.3-1.3) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| 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 |
FDB021980
| KNApSAcK ID |
Not Available
| Chemspider ID |
167259
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00360
| Metagene Link |
HMDB00360
| METLIN ID |
5349
| PubChem Compound |
192742
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Monocrotaline
References |
| Synthesis Reference |
Radej, 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 |
- 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 ]
- 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 ]
- 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 ]
|
PMID: 20505744