Glycylproline (BioDeep_00000017812)

 

Secondary id: BioDeep_00000398319, BioDeep_00000405347

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


(2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid

化学式: C7H12N2O3 (172.0847882)
中文名称: 甘氨酸-L-脯氨酸, 甘油-L-脯氨酸, 甘胺脯氨酸, 甘氨酰-L-脯氨酸
谱图信息: 最多检出来源 Homo sapiens(feces) 2.52%

分子结构信息

SMILES: C1CC(N(C1)C(=O)CN)C(=O)O
InChI: InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)

描述信息

Glycylproline is an end product of collagen metabolism that is further cleaved by prolidase (EC 3.4.13.9); the resulting proline molecules are recycled into collagen or other proteins. Prolidase deficiency is a rare autosomal recessive disease characterized by chronic ulcerative dermatitis, mental retardation, frequent infections and massive urinary excretion of iminodipeptides. The disease has been confirmed to be due to hereditary prolidase deficiency. It has been reported that the activity of the enzyme against glycylproline (Gly-Pro) is almost totally deficient in patients with prolidase deficiency, whereas the activity against other substrates is not so deficient. Some patients with prolidase deficiency have a marked urinary excretion of the iminodipeptide Glycylproline. The urine from patients with pressure sores contains significantly more Glycylproline than the urine from the control. (PMID: 16009141, 7629169, 1536787, 10582130) [HMDB]
Glycylproline is a dipeptide composed of glycine and proline, and is an end product of collagen metabolism that is further cleaved by prolidase (EC 3.4.13.9). The resulting proline molecules are recycled into collagen or other proteins. Prolidase deficiency is a rare autosomal recessive disease characterized by chronic ulcerative dermatitis, mental retardation, frequent infections, and massive urinary excretion of iminodipeptides. Patients with this disease have reportedly decreased prolidase enzyme activity against glycylproline (Gly-Pro). The enzymes activity against other substrates is not as affected. Some patients with prolidase deficiency have a marked urinary excretion of glycylproline. Patients with pressure sores contain significantly more urinary glycylproline than the control (PMID: 16009141, 7629169, 1536787, 10582130).
H-Gly-Pro-OH is an end product of collagen metabolism that is further cleaved by prolidase.
H-Gly-Pro-OH is an end product of collagen metabolism that is further cleaved by prolidase.

同义名列表

21 个代谢物同义名

(2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid; (S)-1-(2-Aminoacetyl)pyrrolidine-2-carboxylic acid; Glycine proline dipeptide; Glycine-proline dipeptide; 1-(Aminoacetyl)proline; 1-Glycyl-L-proline; N-Glycyl-L-proline; Glycyl-L-proline; 1-Glycylproline; N-Glycylproline; Glycyl-proline; g-p Dipeptide; Glycylproline; H-Gly-Pro-OH; GP Dipeptide; Gly-L-pro; NSC 97929; Gly-pro; GP; Glycylproline; Glycyl-L-proline



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • HaiVin Kim, YoungSu Jang, JaeSang Ryu, DaHye Seo, Sak Lee, SungSoo Choi, DongHyun Kim, SangHyun Moh, JungU Shin. The Dipeptide Gly-Pro (GP), Derived from Hibiscus sabdariffa, Exhibits Potent Antifibrotic Effects by Regulating the TGF-β1-ATF4-Serine/Glycine Biosynthesis Pathway. International journal of molecular sciences. 2023 Sep; 24(17):. doi: 10.3390/ijms241713616. [PMID: 37686422]
  • Pathomwat Wongrattanakamon, Wipawadee Yooin, Busaban Sirithunyalug, Piyarat Nimmanpipug, Supat Jiranusornkul. Tentative Peptide‒Lipid Bilayer Models Elucidating Molecular Behaviors and Interactions Driving Passive Cellular Uptake of Collagen-Derived Small Peptides. Molecules (Basel, Switzerland). 2021 Jan; 26(3):. doi: 10.3390/molecules26030710. [PMID: 33573083]
  • Divya Kumar, Vivek K Hamse, K N Neema, Priya Babu Shubha, D M Chetan, Nanjunda Swamy Shivananju. Purification and biochemical characterization of a novel secretory dipeptidyl peptidase IV from porcine serum. Molecular and cellular biochemistry. 2020 Aug; 471(1-2):71-80. doi: 10.1007/s11010-020-03766-y. [PMID: 32577945]
  • Hyun-Jun Lee, Hye-Lim Jang, Dong-Kyu Ahn, Hun-Jung Kim, Hee Young Jeon, Dae Bang Seo, Ji-Hae Lee, Jin Kyu Choi, Seok-Seong Kang. Orally administered collagen peptide protects against UVB-induced skin aging through the absorption of dipeptide forms, Gly-Pro and Pro-Hyp. Bioscience, biotechnology, and biochemistry. 2019 Jun; 83(6):1146-1156. doi: 10.1080/09168451.2019.1580559. [PMID: 30739561]
  • Caixia Ren, Jia Liu, Juntuo Zhou, Hui Liang, Yayun Wang, Yinping Sun, Bin Ma, Yuxin Yin. Low levels of serum serotonin and amino acids identified in migraine patients. Biochemical and biophysical research communications. 2018 02; 496(2):267-273. doi: 10.1016/j.bbrc.2017.11.203. [PMID: 29294327]
  • L A Lyapina, M E Grigor'eva, T Yu Obergan, T A Shubina, L A Andreeva, N F Myasoedov. [Peptide Regulation of Metabolic Processes under Hypercholesterinemia Conditions of an Organism]. Izvestiia Akademii nauk. Seriia biologicheskaia. 2015 Nov; ?(6):634-44. doi: ". [PMID: 26852483]
  • Zhijing Feng, Xiaowei Sun, Jindan Yang, Dongfang Hao, Longfei Du, Hong Wang, Wei Xu, Xiujuan Zhao, Changhao Sun. Metabonomics analysis of urine and plasma from rats given long-term and low-dose dimethoate by ultra-performance liquid chromatography-mass spectrometry. Chemico-biological interactions. 2012 Sep; 199(3):143-53. doi: 10.1016/j.cbi.2012.07.004. [PMID: 22884955]
  • Özgül İnceoğlu, Joana Falcão Salles, Jan Dirk van Elsas. Soil and cultivar type shape the bacterial community in the potato rhizosphere. Microbial ecology. 2012 Feb; 63(2):460-70. doi: 10.1007/s00248-011-9930-8. [PMID: 21898103]
  • Antonio Trani, Giuseppe Gambacorta, Pasqua Loizzo, Giovanna Alviti, Alessandra Schena, Michele Faccia, Lucia Aquilanti, Sara Santarelli, Aldo Di Luccia. Biochemical traits of Ciauscolo, a spreadable typical Italian dry-cured sausage. Journal of food science. 2010 Aug; 75(6):C514-24. doi: 10.1111/j.1750-3841.2010.01703.x. [PMID: 20722905]
  • Takanori Hironaka, Shota Itokawa, Ken-ichi Ogawara, Kazutaka Higaki, Toshikiro Kimura. Quantitative evaluation of PEPT1 contribution to oral absorption of cephalexin in rats. Pharmaceutical research. 2009 Jan; 26(1):40-50. doi: 10.1007/s11095-008-9703-3. [PMID: 18784906]
  • Griet Van Zeebroeck, Beatriz Monge Bonini, Matthias Versele, Johan M Thevelein. Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor. Nature chemical biology. 2009 Jan; 5(1):45-52. doi: 10.1038/nchembio.132. [PMID: 19060912]
  • Irfan Erol, Kwang-Cheol Jeong, David J Baumler, Boris Vykhodets, Sang Ho Choi, Charles W Kaspar. H-NS controls metabolism and stress tolerance in Escherichia coli O157:H7 that influence mouse passage. BMC microbiology. 2006 Aug; 6(?):72. doi: 10.1186/1471-2180-6-72. [PMID: 16911800]
  • L A Liapina, V E Pastorova, T Iu Obergan, G E Samonina, I P Ashmarin, N F Miasoedov. [Comparison of anticoagulant effects of regulatory proline-containing oligopeptides. Specificity of glyprolines, semax, and selank and potential of their practical application]. Izvestiia Akademii nauk. Seriia biologicheskaia. 2006 Mar; ?(2):193-203. doi: NULL. [PMID: 16634437]
  • K A Cherkasova, L A Lyapina, I P Ashmarin. Comparative study of modulatory effects of Semax and primary proline-containing peptides on hemostatic reactions. Bulletin of experimental biology and medicine. 2001 Jul; 132(1):625-6. doi: 10.1023/a:1012503606536. [PMID: 11687836]
  • J Le, C Perier, S Peyroche, F Rascle, M A Blanchon, R Gonthier, J Frey, A Chamson. Urine glycyl-L-proline increase and skin trophicity. Amino acids. 1999; 17(3):315-22. doi: 10.1007/bf01366930. [PMID: 10582130]
  • H Wang, Y J Fei, V Ganapathy, F H Leibach. Electrophysiological characteristics of the proton-coupled peptide transporter PEPT2 cloned from rat brain. The American journal of physiology. 1998 10; 275(4):C967-75. doi: 10.1152/ajpcell.1998.275.4.c967. [PMID: 9755050]
  • V E Pastorova, L A Liapina, T Iu Smolina, I P Ashmarin. [Anticoagulant and fibrinolytic effects of proline-containing peptides]. Izvestiia Akademii nauk. Seriia biologicheskaia. 1998 May; ?(3):390-4. doi: NULL. [PMID: 9644912]
  • I P Ashmarin, E P Karazeeva, L A Lyapina, G E Samonina. The simplest proline-containing peptides PG, GP, PGP, and GPGG: regulatory activity and possible sources of biosynthesis. Biochemistry. Biokhimiia. 1998 Feb; 63(2):119-24. doi: . [PMID: 9526102]
  • A Tanoue, F Endo. [Prolidase deficiency]. Ryoikibetsu shokogun shirizu. 1998; ?(18 Pt 1):160-2. doi: NULL. [PMID: 9590016]
  • M Maffia, T Verri, A Danieli, M Thamotharan, M Pastore, G A Ahearn, C Storelli. H(+)-glycyl-L-proline cotransport in brush-border membrane vesicles of eel (Anguilla anguilla) intestine. The American journal of physiology. 1997 Jan; 272(1 Pt 2):R217-25. doi: 10.1152/ajpregu.1997.272.1.r217. [PMID: 9039012]
  • W L Mock, Y Liu. Hydrolysis of picolinylprolines by prolidase. A general mechanism for the dual-metal ion containing aminopeptidases. The Journal of biological chemistry. 1995 Aug; 270(31):18437-46. doi: 10.1074/jbc.270.31.18437. [PMID: 7629169]
  • M Dolenga, P Hechtman. Prolidase deficiency in cultured human fibroblasts: biochemical pathology and iminodipeptide-enhanced growth. Pediatric research. 1992 Oct; 32(4):479-82. doi: 10.1203/00006450-199210000-00020. [PMID: 1437403]
  • E Berardesca, D Fideli, M Bellosta, K M Dyne, G Zanaboni, G Cetta. Blood transfusions in the therapy of a case of prolidase deficiency. The British journal of dermatology. 1992 Feb; 126(2):193-5. doi: 10.1111/j.1365-2133.1992.tb07820.x. [PMID: 1536787]
  • H A Skopicki, K Fisher, D Zikos, R Bloch, G Flouret, D R Peterson. Multiple carriers for dipeptide transport: carrier-mediated transport of glycyl-L-proline in renal BBMV. The American journal of physiology. 1991 Oct; 261(4 Pt 2):F670-8. doi: 10.1152/ajprenal.1991.261.4.f670. [PMID: 1928378]
  • H Lochs, E L Morse, S A Adibi. Uptake and metabolism of dipeptides by human red blood cells. The Biochemical journal. 1990 Oct; 271(1):133-7. doi: 10.1042/bj2710133. [PMID: 2222407]
  • M C Fonteles, J V Oliveira, K M Carvalho. Metabolism of dipeptides by isolated and perfused nonfiltering kidneys. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 1990; 23(9):785-7. doi: NULL. [PMID: 2101317]
  • Y B Lombardo, E L Morse, S A Adibi. Specificity and mechanism of influence of amino acid residues on hepatic clearance of oligopeptides. The Journal of biological chemistry. 1988 Sep; 263(26):12920-6. doi: . [PMID: 3417643]
  • Z H Endre, P W Kuchel. Proton NMR spectroscopy of rabbit renal cortex. Kidney international. 1985 Jul; 28(1):6-10. doi: 10.1038/ki.1985.110. [PMID: 4046325]
  • V Ganapathy, S J Pashley, R A Roesel, D H Pashley, F H Leibach. Inhibition of rat and human prolidases by captopril. Biochemical pharmacology. 1985 Apr; 34(8):1287-91. doi: 10.1016/0006-2952(85)90507-6. [PMID: 3888225]
  • J Butterworth, D A Priestman. Presence in human cells and tissues of two prolidases and their alteration in prolidase deficiency. Journal of inherited metabolic disease. 1985; 8(4):193-7. doi: 10.1007/bf01805434. [PMID: 3939542]
  • G F King, P W Kuchel. A proton n.m.r. study of iminodipeptide transport and hydrolysis in the human erythrocyte. Possible physiological roles for the coupled system. The Biochemical journal. 1984 Jun; 220(2):553-60. doi: 10.1042/bj2200553. [PMID: 6743286]
  • H Mikasa, K Sasaki, H Kodama, J Arata, M Ikeda. Isotachophoretic analysis of iminopeptides in the urine of patients with iminopeptiduria. Journal of chromatography. 1984 Jan; 305(1):204-9. doi: 10.1016/s0378-4347(00)83331-9. [PMID: 6707145]
  • V Ganapathy, F H Leibach. Role of pH gradient and membrane potential in dipeptide transport in intestinal and renal brush-border membrane vesicles from the rabbit. Studies with L-carnosine and glycyl-L-proline. The Journal of biological chemistry. 1983 Dec; 258(23):14189-92. doi: NULL. [PMID: 6643475]
  • I Myara, C Charpentier, A Lemonnier. Optimal conditions for prolidase assay by proline colorimetric determination: application to iminodipeptiduria. Clinica chimica acta; international journal of clinical chemistry. 1982 Oct; 125(2):193-205. doi: 10.1016/0009-8981(82)90196-6. [PMID: 7139961]
  • V Ganapathy, J Mendicino, F H Leibach. Evidence for a dipeptide transport system in renal brush border membranes from rabbit. Biochimica et biophysica acta. 1981 Apr; 642(2):381-91. doi: 10.1016/0005-2736(81)90454-5. [PMID: 7284363]
  • V Ganapathy, J F Mendicino, F H Leibach. Transport of glycyl-L-proline into intestinal and renal brush border vesicles from rabbit. The Journal of biological chemistry. 1981 Jan; 256(1):118-24. doi: 10.1016/s0021-9258(19)70106-9. [PMID: 7451429]
  • C Charpentier, K Dagbovie, A Lemonnier, M Larregue, R A Johnstone. Prolidase deficiency with iminodipeptiduria: biochemical investigations and first results of attempted therapy. Journal of inherited metabolic disease. 1981; 4(2):77-8. doi: 10.1007/bf02263599. [PMID: 6790856]
  • C R SCRIVER. GLYCYL-PROLINE IN URINE OF HUMANS WITH BONE DISEASE. Canadian journal of physiology and pharmacology. 1964 May; 42(?):357-64. doi: 10.1139/y64-043. [PMID: 14324167]