You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 4.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2020-02-26 21:22:05 UTC |
---|
HMDB ID | HMDB0000351 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | (2S,3R)-3-Hydroxy-2-methylbutanoic acid |
---|
Description | 3-Hydroxy-2-methylbutanoic acid (HMBA) is a normal urinary metabolite involved in isoleucine catabolism, beta-oxidation of fatty acids, and ketogenesis. HMDB is excreted in abnormally high amounts in beta-ketothiolase deficiency. Differences in the enantiomeric ratio of HMBA may originate from the enantioselectivity of different enzyme systems (PMID: 10755375 ). |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
3-Hydroxy-2-methyl-[R-(R,S)]-butanoate | Generator | 3-Hydroxy-2-methyl-[R-(r*,s*)]-butanoate | HMDB | 3-Hydroxy-2-methyl-[R-(r*,s*)]-butanoic acid | HMDB | (2S,3R)-3-Hydroxy-2-methylbutanoic acid | HMDB | (2S,3R)-3-Hydroxy-2-methylbutyric acid | HMDB | (2S,3R)-Nilic acid | HMDB | 3-Hydroxy-2-methyl-[R-(R,S)]-butanoic acid | HMDB | HMBA | HMDB |
|
---|
Chemical Formula | C5H10O3 |
---|
Average Molecular Weight | 118.1311 |
---|
Monoisotopic Molecular Weight | 118.062994186 |
---|
IUPAC Name | (2S,3R)-3-hydroxy-2-methylbutanoic acid |
---|
Traditional Name | (2S,3R)-3-hydroxy-2-methylbutanoic acid |
---|
CAS Registry Number | 71526-30-2 |
---|
SMILES | C[C@@H](O)[C@H](C)C(O)=O |
---|
InChI Identifier | InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4+/m0/s1 |
---|
InChI Key | VEXDRERIMPLZLU-IUYQGCFVSA-N |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acids and conjugates |
---|
Direct Parent | Hydroxy fatty acids |
---|
Alternative Parents | |
---|
Substituents | - Beta-hydroxy acid
- Branched fatty acid
- Hydroxy fatty acid
- Short-chain hydroxy acid
- Methyl-branched fatty acid
- Hydroxy acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Disposition | Route of exposure: Biological location: Source: |
---|
Process | Naturally occurring process: |
---|
Role | Biological role: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
| Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0097-9100000000-4296c67313a78a015074 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00y1-9820000000-7256ed8afed29ebf4daa | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0r0r-9200000000-a7d6bf6e90c8c752f69c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4j-9000000000-fe9a2716010ffb94cff8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4l-9000000000-715b545170085466a6b2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uxr-3900000000-d8f24d02712f429591a7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zgi-9800000000-0821ba5748054e7de369 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-e5b2f743cb4dd5e99ec5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-5900000000-587bb9b1fdf10856b3a1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05fr-9100000000-a33491d8a46967cdd2d3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-1ec2b5bb3af9f3c925ca | Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | Not Available |
---|
Biospecimen Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| Not Available |
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB021974 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 13628066 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | 5340 |
---|
PubChem Compound | 12313370 |
---|
PDB ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | |
---|
References |
---|
Synthesis Reference | Neri, Claudia; Williams, Jonathan M. J. Racemic auxiliaries: applications to asymmetric synthesis. Tetrahedron Letters (2002), 43(23), 4257-4260. |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - Heil M, Podebrad F, Prado E, Beck T, Mosand A, Sewell AC, Bohles H, Lehnert W: Enantioselective analysis of ketone bodies in patients with beta-ketothiolase deficiency, medium-chain acyl coenzyme A dehydrogenase deficiency and ketonemic vomiting. J Chromatogr B Biomed Sci Appl. 2000 Mar 10;739(2):313-24. [PubMed:10755375 ]
|
---|