1.0 2010-04-08 22:05:53 UTC 2019-11-26 02:59:26 UTC FDB003618 gamma-L-Glutamyl-L-phenylalanine Glutamylphenylalanine is a gamma-glutamyl derivative. It is probably formed by transpeptidation between glutathione and the corresponding amino acid, catalyzed by gamma-glutamyl transpeptidase (PMID 237763). It can be detected in urine of patients with phenylketonuria, which is a is a human genetic disorder due to the lack of phenylalanine hydroxylase to metabolize phenylalanine to tyrosine . gamma-L-Glutamyl-L-phenylalanine is found in soft-necked garlic. Gamma-glu-phe Gamma-glutamylphenylalanine H-gamma-glu-phe-oh H-glu(phe-oh)-oh L-gamma-glutamyl-l-phenylalanine N-(gamma-l-glutamyl)phenylalanine N-L-gamma-Glutamyl-3-phenyl-L-alanine N-l-gamma-glutamyl-l-phenylalanine C14H18N2O5 294.3031 294.121571696 2-amino-4-[(1-carboxy-2-phenylethyl)-C-hydroxycarbonimidoyl]butanoic acid 2-amino-4-[(1-carboxy-2-phenylethyl)-C-hydroxycarbonimidoyl]butanoic acid 7432-24-8 NC(CC\C(O)=N\C(CC1=CC=CC=C1)C(O)=O)C(O)=O InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21) XHHOHZPNYFQJKL-UHFFFAOYSA-N belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Dipeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic homomonocyclic compounds Alpha amino acids Amino acids Amphetamines and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Gamma-glutamyl amino acids Glutamine and derivatives Hydrocarbon derivatives Monoalkylamines N-acyl amines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Phenylalanine and derivatives Phenylpropanoic acids Secondary carboxylic acid amides 3-phenylpropanoic-acid Alpha-amino acid Alpha-amino acid or derivatives Alpha-dipeptide Amine Amino acid Amino acid or derivatives Amphetamine or derivatives Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid Dicarboxylic acid or derivatives Fatty acyl Fatty amide Gamma-glutamyl alpha-amino acid Glutamine or derivatives Hydrocarbon derivative Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalanine or derivatives Primary aliphatic amine Primary amine Secondary carboxylic acid amide dipeptide Solid logp -2.04 ALOGPS logs -2.73 ALOGPS solubility 5.54e-01 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac 2-amino-4-[(1-carboxy-2-phenylethyl)-C-hydroxycarbonimidoyl]butanoic acid ChemAxon average_mass 294.3031 ChemAxon mono_mass 294.121571696 ChemAxon smiles NC(CC\C(O)=N\C(CC1=CC=CC=C1)C(O)=O)C(O)=O ChemAxon formula C14H18N2O5 ChemAxon inchi InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21) ChemAxon inchikey XHHOHZPNYFQJKL-UHFFFAOYSA-N ChemAxon polar_surface_area 133.21 ChemAxon refractivity 73.73 ChemAxon polarizability 29.25 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26318 Specdb::CMs 41454 Specdb::MsMs 11162 Specdb::MsMs 11163 Specdb::MsMs 11164 Specdb::MsMs 17834 Specdb::MsMs 17835 Specdb::MsMs 17836 HMDB00594 #<Reference:0x000055ce325155a8> #<Reference:0x000055ce325153f0> #<Reference:0x000055ce32515238> #<Reference:0x000055ce32515030> #<Reference:0x000055ce32514e78> #<Reference:0x000055ce32514cc0> Soft-necked garlic Type 1 specific Allium sativum L. var. sativum 4682