Record Information |
---|
Version | 1.0 |
---|
Creation date | 2011-09-21 00:05:57 UTC |
---|
Update date | 2015-10-09 22:33:40 UTC |
---|
Primary ID | FDB021963 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | 2-Methylbutyrylglycine |
---|
Description | 2-Methylbutyrylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:
acyl-CoA + glycine < -- > CoA + N-acylglycine. The isolated excretion of 2-methylbutyrylglycine (2-MBG) is the hallmark of short/branched-chain acyl-CoA dehydrogenase deficiency (PubMedID 15615815). A number of previously unrecognized abnormal metabolites have been identified and quantitated in the urine of patients with propionyl-CoA carboxylase deficiency. These include the isoleucine metabolites, 2-methyl-3-hydroxybutyric acid and 2-methylacetoacetic acid. Additionally, 3-hydroxyvaleric acid and 3-oxovaleric acid were found, which may be products of the condensation of propionyl-CoA with acetyl-CoA catalyzed by 3-oxoacyl-CoA thiolases. Following a load of isoleucine, 2-methylbutyrylglycine was identified. This metabolite has not previously been observed in man. (PMID: 630060) [HMDB] |
---|
CAS Number | 52320-67-9 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
alpha-Methylbutyrylglycine | ChEBI | a-Methylbutyrylglycine | Generator | Α-methylbutyrylglycine | Generator | (2-Methyl-butyrylamino)-acetate | HMDB | (2-Methyl-butyrylamino)-acetic acid | HMDB | 2-MBG | HMDB | 2-Methylbutyryl glycine | HMDB | N-(2-Methylbutyryl)glycine | HMDB | N-Sec-valerylglycine | HMDB | 2-Methylbutyrylglycine | ChEBI | (2-methyl-butyrylamino)-acetate | hmdb | (2-methyl-butyrylamino)-acetic acid | hmdb | N-sec-Valerylglycine | hmdb |
|
---|
Predicted Properties | |
---|
Chemical Formula | C7H13NO3 |
---|
IUPAC name | 2-(2-methylbutanamido)acetic acid |
---|
InChI Identifier | InChI=1S/C7H13NO3/c1-3-5(2)7(11)8-4-6(9)10/h5H,3-4H2,1-2H3,(H,8,11)(H,9,10) |
---|
InChI Key | HOACIBQKYRHBOW-UHFFFAOYSA-N |
---|
Isomeric SMILES | CCC(C)C(=O)NCC(O)=O |
---|
Average Molecular Weight | 159.183 |
---|
Monoisotopic Molecular Weight | 159.089543287 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | N-acyl-alpha amino acids |
---|
Alternative Parents | |
---|
Substituents | - N-acyl-alpha-amino acid
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | Not Available | |
---|
Melting Point | Not Available | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
Predicted GC-MS | 2-Methylbutyrylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4r-9200000000-037c365f69a94a2795e3 | Spectrum | Predicted GC-MS | 2-Methylbutyrylglycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9100000000-e433d3dc8126ab0a8a11 | Spectrum | Predicted GC-MS | 2-Methylbutyrylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2-Methylbutyrylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2-Methylbutyrylglycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2-Methylbutyrylglycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2-Methylbutyrylglycine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a70-9000000000-677b36115959d21d1f09 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-9000000000-8acb9e6da8ae025a1f8d | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4l-9000000000-e9d59f38263024d831c0 | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-5b8594d1ae20d3cefd30 | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9100000000-5616d01ed9501db46e06 | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-dc3a1247ae093f314b43 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-9000000000-3dfb1ee5e780367552f0 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-05fr-8900000000-1ee8e7b73ae88fd1ef8f | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-d2b9a5139d838d79d4cc | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dr-5900000000-0b42996566d3baf8c66b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06ri-9400000000-711387fe57829069d6f3 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-6fc57261ee60bbc3af11 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-1fa66530dedcfabf00e7 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-2900000000-975416bc76e2d0f660c1 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ab9-9000000000-d1bb15a1be690ed64b19 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0bt9-9400000000-c1ffbc1b6124d8ccd7f3 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-d49a18704d3772cb3e92 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-5f02bb141e31e9a67e6a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-1900000000-7a07dd16a49c33b82c5c | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05fu-9600000000-2a213e61a98edbd8d71a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fu-9000000000-8a65567da0b6dd8bfb83 | Spectrum |
|
---|
NMR | |
---|
External Links |
---|
ChemSpider ID | 168243 |
---|
ChEMBL ID | CHEMBL314835 |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | 193872 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB00339 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Name | Gene Name | UniProt ID |
---|
Glycine N-acyltransferase | GLYAT | Q6IB77 | Glycine N-acyltransferase-like protein 1 | GLYATL1 | Q969I3 | Glycine N-acyltransferase-like protein 2 | GLYATL2 | Q8WU03 | Glycine N-acyltransferase-like protein 3 | GLYATL3 | Q5SZD4 |
|
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|