| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:33 -0600 |
| Update Date |
2013-05-31 11:32:01 -0600 |
| HMDB ID |
HMDB02042 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
3-Phenylpropionylglycine |
| Description |
3-Phenylpropionylglycine 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-acylglycineUrinary excretion of 3-phenylpropionylglycine is a diagnostic marker for medium-chain acyl-CoA dehydrogenase deficiency. 3-phenylpropionylglycine is derived from 3-phenylpropionic acid, a product of anaerobic bacterial metabolism in the gut. (PMID 1541011  ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
|
| Chemical Formula |
C11H13NO3 |
| Average Molecular Weight |
207.2258 |
| Monoisotopic Molecular Weight |
207.089543287 |
| IUPAC Name |
2-[(3-oxo-3-phenylpropyl)amino]acetic acid |
| Traditional IUPAC Name |
[(3-oxo-3-phenylpropyl)amino]acetic acid |
| CAS Registry Number |
20989-69-9 |
| SMILES |
OC(=O)CNCCC(=O)C1=CC=CC=C1 |
| InChI Identifier |
InChI=1S/C11H13NO3/c13-10(6-7-12-8-11(14)15)9-4-2-1-3-5-9/h1-5,12H,6-8H2,(H,14,15) |
| InChI Key |
XHSURMJJKAFELI-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Aromatic Homomonocyclic Compounds
|
| Substituents |
- Acetophenone
- Benzoyl
- Beta Aminoketone
- Carboxylic Acid
- Ketone
- Secondary Aliphatic Amine (Dialkylamine)
|
| Direct Parent |
Alpha Amino Acids and Derivatives |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
Not Available
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| Application |
Not Available
|
| Cellular locations |
- Membrane (predicted from logP)
|
| 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 |
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| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
- Membrane (predicted from logP)
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
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| 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 |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022813 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
1296138 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB02042 |
| Metagene Link |
HMDB02042 |
| METLIN ID |
6455 |
| PubChem Compound |
1608346 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: Stable isotope dilution analysis of n-hexanoylglycine, 3-phenylpropionylglycine and suberylglycine in human urine using chemical ionization gas chromatography/mass spectrometry selected ion monitoring. Biomed Environ Mass Spectrom. 1989 Jul;18(7):471-7.
Pubmed: 2775902
- Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: The enzymatic basis for the dehydrogenation of 3-phenylpropionic acid: in vitro reaction of 3-phenylpropionyl-CoA with various acyl-CoA dehydrogenases. Pediatr Res. 1990 May;27(5):501-7.
Pubmed: 2345678
- Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71.
Pubmed: 2380628
- Bennett MJ, Bhala A, Poirier SF, Ragni MC, Willi SM, Hale DE: When do gut flora in the newborn produce 3-phenylpropionic acid? Implications for early diagnosis of medium-chain acyl-CoA dehydrogenase deficiency. Clin Chem. 1992 Feb;38(2):278-81.
Pubmed: 1541011
|
