1.0 2016-09-30 22:33:18 UTC 2020-05-11 20:37:15 UTC BMDB0000594 BMDB00594 Glutamylphenylalanine (2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid L-gamma-Glu-L-phe L-gamma-Glutamyl-L-phenylalanine N-(gamma-L-Glutamyl)phenylalanine N-L-gamma-Glutamyl-3-phenyl-L-alanine N-L-gamma-Glutamyl-L-phenylalanine (2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoate L-g-Glu-L-phe L-Γ-glu-L-phe L-g-Glutamyl-L-phenylalanine L-Γ-glutamyl-L-phenylalanine N-(g-L-Glutamyl)phenylalanine N-(Γ-L-glutamyl)phenylalanine N-L-g-Glutamyl-3-phenyl-L-alanine N-L-Γ-glutamyl-3-phenyl-L-alanine N-L-g-Glutamyl-L-phenylalanine N-L-Γ-glutamyl-L-phenylalanine g-Glutamylphenylalanine Γ-glutamylphenylalanine gamma-Glu-phe γ-Glu-Phe γ-L-Glu-L-Phe γ-L-Glutamyl-L-phenylalanine N-γ-Glutamylphenylalanine N-L-γ-Glutamylphenylalanine gamma-L-Glu-L-Phe gamma-L-Glutamyl-L-phenylalanine N-gamma-Glutamylphenylalanine N-L-gamma-Glutamylphenylalanine H-γ-Glu-Phe-OH H-gamma-Glu-Phe-OH gamma-Glutamylphenylalanine N-gamma-L-Glutamyl-L-phenylalanine N-γ-L-Glutamyl-L-phenylalanine g-Glu-Phe C14H18N2O5 294.3031 294.121571696 (2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid gamma-glutamylphenylalanine 7432-24-8 N[C@@H](CCC(=O)N[C@@H](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)/t10-,11-/m0/s1 XHHOHZPNYFQJKL-QWRGUYRKSA-N belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Phenylalanine and derivatives Amino acids Amphetamines and derivatives Carbonyl compounds Carboximidic acids Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Phenylpropanoic acids Propargyl-type 1,3-dipolar organic compounds 3-phenylpropanoic-acid Alpha-amino acid Amine Amino acid Amphetamine or derivatives Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Dicarboxylic acid or derivatives Hydrocarbon derivative L-alpha-amino acid Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalanine or derivatives Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound Aromatic homomonocyclic compounds Solid logp -2.15 ALOGPS logs -2.68 ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 1.82 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid ChemAxon average_mass 294.3031 ChemAxon mono_mass 294.121571696 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](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)/t10-,11-/m0/s1 ChemAxon inchikey XHHOHZPNYFQJKL-QWRGUYRKSA-N ChemAxon polar_surface_area 129.72 ChemAxon refractivity 73.2 ChemAxon polarizability 29.7 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 109512 Specdb::MsMs 109513 Specdb::MsMs 109514 Specdb::MsMs 176961 Specdb::MsMs 176962 Specdb::MsMs 176963 Specdb::MsMs 447338 Specdb::MsMs 2745120 Specdb::MsMs 2745121 Specdb::MsMs 2745122 Specdb::MsMs 2937586 Specdb::MsMs 2937587 Specdb::MsMs 2937588 Specdb::CMs 15849 Specdb::CMs 37642 Specdb::CMs 166833 Specdb::CMs 1069394 Specdb::CMs 1069396 Specdb::CMs 1069397 Specdb::CMs 1069399 Specdb::CMs 1069401 Specdb::CMs 1069403 Specdb::CMs 1069405 Specdb::CMs 1069406 Specdb::CMs 1069408 Specdb::CMs 1069410 Specdb::CMs 1069412 Specdb::CMs 1069414 Specdb::CMs 1069415 Specdb::CMs 1069417 Specdb::CMs 1069419 Specdb::CMs 1069421 Specdb::CMs 1069422 Specdb::CMs 1069424 Specdb::CMs 1069426 Specdb::CMs 1069428 Specdb::CMs 1069430 Specdb::NmrOneD 20442 Specdb::NmrOneD 20443 Specdb::NmrOneD 20444 Specdb::NmrOneD 20445 Specdb::NmrOneD 20446 Specdb::NmrOneD 20447 Specdb::NmrOneD 20448 Specdb::NmrOneD 20449 Specdb::NmrOneD 20450 Specdb::NmrOneD 20451 Specdb::NmrOneD 20452 Specdb::NmrOneD 20453 Specdb::NmrOneD 20454 Specdb::NmrOneD 20455 Specdb::NmrOneD 20456 Specdb::NmrOneD 20457 Specdb::NmrOneD 20458 Specdb::NmrOneD 20459 Specdb::NmrOneD 20460 Specdb::NmrOneD 20461 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB112161 99868 111299 89582 Bodnaryk, Robert P. Preparative-scale enzymic synthesis of g-L-glutamyl-L-phenylalanine. Insect Biochemistry (1972), 2(1), 49-52.