We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Bovine Rumen Metabolome Database



Showing metabocard for Phenylacetylglycine (RMDB00821)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:16
Accession Number RMDB00821
Common Name Phenylacetylglycine
Description Phenylacetylglycine 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 Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292)
Synonyms
  1. ((phenylacetyl)amino)acetic acid
  2. N-(Phenylacetyl)glycine
  3. N-(phenylacetyl)-Glycine
  4. N-Phenacetylglycine
  5. N-Phenylacetylglycine
  6. Phenaceturate
  7. Phenaceturic acid
  8. Phenacetylglycine
  9. [(Phenylacetyl)amino]acetate
  10. [(Phenylacetyl)amino]acetic acid
  11. PAA
  12. PAG
  13. phenylacetyl glycine
Chemical IUPAC Name 2-(2-phenylacetyl)aminoacetic acid
Chemical Formula C10H11NO3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Acyl Glycines
Sub Class
  • Aromatic/Heterocyclic glycine conjugates
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid; secondary carboxylic acid amide; aromatic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 193.199
Monoisotopic Molecular Weight 193.073898
Isomeric SMILES OC(=O)CNC(=O)CC1=CC=CC=C1
Canonical SMILES OC(=O)CNC(=O)CC1=CC=CC=C1
KEGG Compound ID C05596 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 4237 Link Image
PubChem Compound 68144 Link Image
PubChem Substance 11389064 Link Image
ChEBI ID Not Available
CAS Registry Number 500-98-1
InChI Identifier InChI=1/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)
Synthesis Reference Ford, Jared H. Convenient synthesis of phenaceturic acid. Journal of the American Chemical Society (1949), 71 3842.
Melting Point (Experimental) Not Available
Experimental Water Solubility 7.3 mg/mL at 11 oC [BEILSTEIN] Source: PhysProp
Predicted Water Solubility 0.663 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 0.51 [Predicted by ALOGPS]; -1.5 [Predicted by PubChem via XLOGP]; -0.53 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 82.38 +/- 9.4 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 58.6 +/- 5.0 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 73 +/- 14 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 136 +/- 33 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 104 +/- 35 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available