1.0 2016-09-30 22:35:29 UTC 2020-05-05 18:39:57 UTC BMDB0000721 BMDB00721 Glycylproline Glycylproline, also known as gly-pro, 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. Glycylproline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glycylproline has been found to be associated with several diseases known as eosinophilic esophagitis, alzheimer's disease, and colorectal cancer; also glycylproline has been linked to the inborn metabolic disorders including prolidase deficiency. 1-(Aminoacetyl)proline 1-Glycylproline Gly-L-pro GP N-Glycyl-L-proline N-Glycylproline Glycyl-L-proline (S)-1-(2-Aminoacetyl)pyrrolidine-2-carboxylic acid 1-Glycyl-L-proline g-p Dipeptide GP Dipeptide Gly-pro Glycine proline dipeptide Glycine-proline dipeptide Glycyl-proline NSC 97929 Glycylproline C7H12N2O3 172.1818 172.08479226 (2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid glycylproline 704-15-4 NCC(=O)N1CCC[C@H]1C(O)=O InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)/t5-/m0/s1 KZNQNBZMBZJQJO-YFKPBYRVSA-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. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Dipeptides Alpha amino acid amides Amino acids Azacyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives N-acyl-L-alpha-amino acids N-acylpyrrolidines Organic oxides Organopnictogen compounds Proline and derivatives Pyrrolidine carboxylic acids Tertiary carboxylic acid amides Aliphatic heteromonocyclic compound Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-dipeptide Amine Amino acid Amino acid or derivatives Azacycle Carbonyl group Carboxamide group Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-l-alpha-amino acid N-acylpyrrolidine Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Proline or derivatives Pyrrolidine Pyrrolidine carboxylic acid Pyrrolidine carboxylic acid or derivatives Tertiary carboxylic acid amide Aliphatic heteromonocyclic compounds dipeptide Solid melting_point 155 - 158 °C logp -2.65 ALOGPS logs 0.21 ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 3.61 ChemAxon pka_strongest_basic 8.13 ChemAxon iupac (2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid ChemAxon average_mass 172.1818 ChemAxon mono_mass 172.08479226 ChemAxon smiles NCC(=O)N1CCC[C@H]1C(O)=O ChemAxon formula C7H12N2O3 ChemAxon inchi InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)/t5-/m0/s1 ChemAxon inchikey KZNQNBZMBZJQJO-YFKPBYRVSA-N ChemAxon polar_surface_area 83.63 ChemAxon refractivity 40.99 ChemAxon polarizability 16.75 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 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::MsIr 790 Specdb::MsIr 791 Specdb::MsIr 792 Specdb::NmrTwoD 2035 Specdb::CMs 1710 Specdb::CMs 102740 Specdb::CMs 102741 Specdb::CMs 152628 Specdb::CMs 1072765 Specdb::CMs 1072767 Specdb::CMs 1072769 Specdb::CMs 1072771 Specdb::MsMs 1310737 Specdb::MsMs 1310738 Specdb::MsMs 1310739 Specdb::MsMs 1425223 Specdb::MsMs 1425224 Specdb::MsMs 1425225 Specdb::MsMs 1448413 Specdb::MsMs 1448414 Specdb::MsMs 1448415 Specdb::MsMs 2226612 Specdb::MsMs 2228094 Specdb::MsMs 2252708 Specdb::MsMs 2253788 Specdb::MsMs 2254731 Specdb::MsMs 2255831 Specdb::MsMs 2256693 Specdb::MsMs 2257912 Specdb::MsMs 2258693 Specdb::MsMs 2259863 Specdb::MsMs 2761852 Specdb::MsMs 2761853 Specdb::MsMs 2761854 Specdb::MsMs 2947341 Specdb::MsMs 2947342 Specdb::MsMs 2947343 Specdb::NmrOneD 5201 Specdb::NmrOneD 20622 Specdb::NmrOneD 20623 Specdb::NmrOneD 20624 Specdb::NmrOneD 20625 Specdb::NmrOneD 20626 Specdb::NmrOneD 20627 Specdb::NmrOneD 20628 Specdb::NmrOneD 20629 Specdb::NmrOneD 20630 Specdb::NmrOneD 20631 Specdb::NmrOneD 20632 Specdb::NmrOneD 20633 Specdb::NmrOneD 20634 Specdb::NmrOneD 20635 Specdb::NmrOneD 20636 Specdb::NmrOneD 20637 Specdb::NmrOneD 20638 Specdb::NmrOneD 20639 Specdb::NmrOneD 20640 Specdb::NmrOneD 20641 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 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 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Commercial whole milk with 3.25% fat Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 Milk Commercial milk, by CIL LC-MS Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 FDB022202 2282246 3013625 70744 CPD-10814 Maruyama, Susumu; Ichimura, Toshiaki; Otsuka, Tatsuo; Yamashita, Eiichi. Long-lasting antihypertensive agents and glycylproline manufactured from collagen and/or gelatin. Jpn. Kokai Tokkyo Koho (2005), 10 pp. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809