Pyrraline (BioDeep_00000618227)
代谢物信息卡片
2-amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid
化学式: C12H18N2O4 (254.1266508)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=C(N(C(=C1)C=O)CCCCC(C(=O)O)N)CO
InChI: InChI=1S/C12H18N2O4/c13-11(12(17)18)3-1-2-6-14-9(7-15)4-5-10(14)8-16/h4-5,7,11,16H,1-3,6,8,13H2,(H,17,18)
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:59973
- PubChem: 122228
- PubChem: 14274616
- Metlin: METLIN89025
- CAS: 74509-14-1
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)
0 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
- Hugues Fouotsa, Pierre Mkounga, Alain Meli Lannang, Jérôme Vanheuverzwijn, Zhiyu Zhou, Karine Leblanc, Somia Rharrabti, Augustin Ephrem Nkengfack, Jean-François Gallard, Véronique Fontaine, Franck Meyer, Erwan Poupon, Pierre Le Pogam, Mehdi A Beniddir. Pyrrovobasine, hybrid alkylated pyrraline monoterpene indole alkaloid pseudodimer discovered using a combination of mass spectral and NMR-based machine learning annotations.
Organic & biomolecular chemistry.
2021 12; 20(1):98-105. doi:
10.1039/d1ob01791h. [PMID: 34596204] - Christoph Hohmann, Kristin Liehr, Christian Henning, Roman Fiedler, Matthias Girndt, Michael Gebert, Michael Hulko, Markus Storr, Marcus A Glomb. Detection of Free Advanced Glycation End Products in Vivo during Hemodialysis.
Journal of agricultural and food chemistry.
2017 Feb; 65(4):930-937. doi:
10.1021/acs.jafc.6b05013. [PMID: 28112514] - Caronda J Moore, Chun Hong Shao, Ryoji Nagai, Shelby Kutty, Jaipaul Singh, Keshore R Bidasee. Malondialdehyde and 4-hydroxynonenal adducts are not formed on cardiac ryanodine receptor (RyR2) and sarco(endo)plasmic reticulum Ca2+-ATPase (SERCA2) in diabetes.
Molecular and cellular biochemistry.
2013 Apr; 376(1-2):121-35. doi:
10.1007/s11010-013-1558-1. [PMID: 23354458] - Stefanie Geissler, Michael Hellwig, Madlen Zwarg, Fritz Markwardt, Thomas Henle, Matthias Brandsch. Transport of the advanced glycation end products alanylpyrraline and pyrralylalanine by the human proton-coupled peptide transporter hPEPT1.
Journal of agricultural and food chemistry.
2010 Feb; 58(4):2543-7. doi:
10.1021/jf903791u. [PMID: 20104847] - Michael Hellwig, Stefanie Geissler, Anett Peto, Ilka Knütter, Matthias Brandsch, Thomas Henle. Transport of free and peptide-bound pyrraline at intestinal and renal epithelial cells.
Journal of agricultural and food chemistry.
2009 Jul; 57(14):6474-80. doi:
10.1021/jf901224p. [PMID: 19555106] - Waqar Ahmad, Lili Li, Yulin Deng. Identification of AGE-precursors and AGE formation in glycation-induced BSA peptides.
BMB reports.
2008 Jul; 41(7):516-22. doi:
10.5483/bmbrep.2008.41.7.516. [PMID: 18682035] - Katsumi Mera, Makoto Anraku, Kenichiro Kitamura, Keisuke Nakajou, Toru Maruyama, Kimio Tomita, Masaki Otagiri. Oxidation and carboxy methyl lysine-modification of albumin: possible involvement in the progression of oxidative stress in hemodialysis patients.
Hypertension research : official journal of the Japanese Society of Hypertension.
2005 Dec; 28(12):973-80. doi:
10.1291/hypres.28.973. [PMID: 16671336] - José D Méndez, Lidia I Leal. Inhibition of in vitro pyrraline formation by L-arginine and polyamines.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2004 Dec; 58(10):598-604. doi:
10.1016/j.biopha.2004.09.004. [PMID: 15589069] - Tadashi Jono, Ryoji Nagai, Xia Lin, Naila Ahmed, Paul J Thornalley, Motohiro Takeya, Seikoh Horiuchi. Nepsilon-(Carboxymethyl)lysine and 3-DG-imidazolone are major AGE structures in protein modification by 3-deoxyglucosone.
Journal of biochemistry.
2004 Sep; 136(3):351-8. doi:
10.1093/jb/mvh124. [PMID: 15598892] - Tadashi Kiho, Shigeyuki Usui, Kazuyuki Hirano, Koichi Aizawa, Takahiro Inakuma. Tomato paste fraction inhibiting the formation of advanced glycation end-products.
Bioscience, biotechnology, and biochemistry.
2004 Jan; 68(1):200-5. doi:
10.1271/bbb.68.200. [PMID: 14745184] - A Foerster, T Henle. Glycation in food and metabolic transit of dietary AGEs (advanced glycation end-products): studies on the urinary excretion of pyrraline.
Biochemical Society transactions.
2003 Dec; 31(Pt 6):1383-5. doi:
10.1042/bst0311383. [PMID: 14641068] - Hirokazu Tsukahara, Rumiko Shibata, Naoko Ohta, Shuko Sato, Masahiro Hiraoka, Setsuko Ito, Eisei Noiri, Mitsufumi Mayumi. High levels of urinary pentosidine, an advanced glycation end product, in children with acute exacerbation of atopic dermatitis: relationship with oxidative stress.
Metabolism: clinical and experimental.
2003 Dec; 52(12):1601-5. doi:
10.1016/s0026-0495(03)00310-x. [PMID: 14669163] - Hirokazu Tsukahara, KyouchiI Sekine, Mayumi Uchiyama, Hisako Kawakami, Ikue Hata, Yukiko Todoroki, Masahiro Hiraoka, Masayuki Kaji, Tohru Yorifuji, Toru Momoi, Kazuhiro Yoshihara, Masatoshi Beppu, Mitsufumi Mayumi. Formation of advanced glycosylation end products and oxidative stress in young patients with type 1 diabetes.
Pediatric research.
2003 Sep; 54(3):419-24. doi:
10.1203/01.pdr.0000076662.72100.74. [PMID: 12761359] - Makoto Daimon, Kazuhiko Sugiyama, Wataru Kameda, Tamotsu Saitoh, Toshihide Oizumi, Akihiko Hirata, Hiroshi Yamaguchi, Hiroshi Ohnuma, Masahiko Igarashi, Takeo Kato. Increased urinary levels of pentosidine, pyrraline and acrolein adduct in type 2 diabetes.
Endocrine journal.
2003 Feb; 50(1):61-7. doi:
10.1507/endocrj.50.61. [PMID: 12733710] - Martin Zeier, Vedat Schwenger, Reinhold Deppisch, Ulrike Haug, Kai Weigel, U Bahner, Christoph Wanner, H Schneider, Thomas Henle, Eberhard Ritz. Glucose degradation products in PD fluids: do they disappear from the peritoneal cavity and enter the systemic circulation?.
Kidney international.
2003 Jan; 63(1):298-305. doi:
10.1046/j.1523-1755.2003.00705.x. [PMID: 12472796] - K Yoshihara, R Kiyonami, Y Shimizu, M Beppu. Determination of urinary pyrraline by solid-phase extraction and high performance liquid chromatography.
Biological & pharmaceutical bulletin.
2001 Aug; 24(8):863-6. doi:
10.1248/bpb.24.863. [PMID: 11510474] - N Shibata, R Nagai, S Miyata, T Jono, S Horiuchi, A Hirano, S Kato, S Sasaki, K Asayama, M Kobayashi. Nonoxidative protein glycation is implicated in familial amyotrophic lateral sclerosis with superoxide dismutase-1 mutation.
Acta neuropathologica.
2000 Sep; 100(3):275-84. doi:
10.1007/s004019900173. [PMID: 10965797] - P Odetti, S Garibaldi, R Norese, G Angelini, L Marinelli, S Valentini, S Menini, N Traverso, D Zaccheo, S Siedlak, G Perry, M A Smith, M Tabaton. Lipoperoxidation is selectively involved in progressive supranuclear palsy.
Journal of neuropathology and experimental neurology.
2000 May; 59(5):393-7. doi:
10.1093/jnen/59.5.393. [PMID: 10888369] - T Henle, R Deppisch, W Beck, O Hergesell, G M Hänsch, E Ritz. Advanced glycated end-products (AGE) during haemodialysis treatment: discrepant results with different methodologies reflecting the heterogeneity of AGE compounds.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
1999 Aug; 14(8):1968-75. doi:
10.1093/ndt/14.8.1968. [PMID: 10462279] - S Mizuiri, S Miyata, K Sakai, M Kobayashi, M Miyagi, T Nakanishi, B F Liu, H Kojima, A Hasegawa. Effect of intraperitoneal administration of heparin on advanced glycation end-products in CAPD.
Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis.
1999 Jul; 19(4):361-5. doi:
10.1177/089686089901900413. [PMID: 10507818] - P Odetti, G Angelini, D Dapino, D Zaccheo, S Garibaldi, F Dagna-Bricarelli, G Piombo, G Perry, M Smith, N Traverso, M Tabaton. Early glycoxidation damage in brains from Down's syndrome.
Biochemical and biophysical research communications.
1998 Feb; 243(3):849-51. doi:
10.1006/bbrc.1998.8186. [PMID: 9501012] - K Horie, T Miyata, K Maeda, S Miyata, S Sugiyama, H Sakai, C van Ypersole de Strihou, V M Monnier, J L Witztum, K Kurokawa. Immunohistochemical colocalization of glycoxidation products and lipid peroxidation products in diabetic renal glomerular lesions. Implication for glycoxidative stress in the pathogenesis of diabetic nephropathy.
The Journal of clinical investigation.
1997 Dec; 100(12):2995-3004. doi:
10.1172/jci119853. [PMID: 9399945] - A D Seftel, N D Vaziri, Z Ni, K Razmjouei, J Fogarty, N Hampel, J Polak, R Z Wang, K Ferguson, C Block, C Haas. Advanced glycation end products in human penis: elevation in diabetic tissue, site of deposition, and possible effect through iNOS or eNOS.
Urology.
1997 Dec; 50(6):1016-26. doi:
10.1016/s0090-4295(97)00512-8. [PMID: 9426743] - M Portero-Otín, R Pamplona, M J Bellmunt, M Bergua, J Prat. Glycaemic control and in vivo non-oxidative Maillard reaction: urinary excretion of pyrraline in diabetes patients.
European journal of clinical investigation.
1997 Sep; 27(9):767-73. doi:
10.1046/j.1365-2362.1997.1900740.x. [PMID: 9352249] - H Shoda, S Miyata, B F Liu, H Yamada, T Ohara, K Suzuki, M Oimomi, M Kasuga. Inhibitory effects of tenilsetam on the Maillard reaction.
Endocrinology.
1997 May; 138(5):1886-92. doi:
10.1210/endo.138.5.5151. [PMID: 9112383] - S Miyata, B F Liu, H Shoda, T Ohara, H Yamada, K Suzuki, M Kasuga. Accumulation of pyrraline-modified albumin in phagocytes due to reduced degradation by lysosomal enzymes.
The Journal of biological chemistry.
1997 Feb; 272(7):4037-42. doi:
10.1074/jbc.272.7.4037. [PMID: 9020111] - M Portero-Otín, R Pamplona, M J Bellmunt, M Bergua, R H Nagaraj, J Prat. Urinary pyrraline as a biochemical marker of non-oxidative Maillard reactions in vivo.
Life sciences.
1997; 60(4-5):279-87. doi:
10.1016/s0024-3205(96)00628-5. [PMID: 9010483] - H Odani, T Shinzato, Y Matsumoto, I Takai, S Nakai, M Miwa, N Iwayama, I Amano, K Maeda. First evidence for accumulation of protein-bound and protein-free pyrraline in human uremic plasma by mass spectrometry.
Biochemical and biophysical research communications.
1996 Jul; 224(1):237-41. doi:
10.1006/bbrc.1996.1013. [PMID: 8694819] - R H Nagaraj, C Sady. The presence of a glucose-derived Maillard reaction product in the human lens.
FEBS letters.
1996 Mar; 382(3):234-8. doi:
10.1016/0014-5793(96)00142-1. [PMID: 8605976] - R H Nagaraj, M Portero-Otin, V M Monnier. Pyrraline ether crosslinks as a basis for protein crosslinking by the advanced Maillard reaction in aging and diabetes.
Archives of biochemistry and biophysics.
1996 Jan; 325(2):152-8. doi:
10.1006/abbi.1996.0019. [PMID: 8561492] - S Sugiyama, T Miyata, K Horie, Y Iida, M Tsuyuki, H Tanaka, K Maeda. Advanced glycation end-products in diabetic nephropathy.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
1996; 11 Suppl 5(?):91-4. doi:
10.1093/ndt/11.supp5.91. [PMID: 9044316] - V M Monnier, R H Nagaraj, M Portero-Otin, M Glomb, A H Elgawish, D R Sell, M A Friedlander. Structure of advanced Maillard reaction products and their pathological role.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
1996; 11 Suppl 5(?):20-6. doi:
10.1093/ndt/11.supp5.20. [PMID: 9044302] - M Portero-Otin, R H Nagaraj, V M Monnier. Chromatographic evidence for pyrraline formation during protein glycation in vitro and in vivo.
Biochimica et biophysica acta.
1995 Feb; 1247(1):74-80. doi:
10.1016/0167-4838(94)00209-y. [PMID: 7873594] - H Yamada, S Miyata, N Igaki, H Yatabe, Y Miyauchi, T Ohara, M Sakai, H Shoda, M Oimomi, M Kasuga. Increase in 3-deoxyglucosone levels in diabetic rat plasma. Specific in vivo determination of intermediate in advanced Maillard reaction.
The Journal of biological chemistry.
1994 Aug; 269(32):20275-80. doi:
10.1016/s0021-9258(17)31987-7. [PMID: 8051120] - P R Smith, H H Somani, P J Thornalley, J Benn, P H Sonksen. Evidence against the formation of 2-amino-6-(2-formyl-5-hydroxymethyl-pyrrol-1-yl)-hexanoic acid ('pyrraline') as an early-stage product or advanced glycation end product in non-enzymic protein glycation.
Clinical science (London, England : 1979).
1993 Jan; 84(1):87-93. doi:
10.1042/cs0840087. [PMID: 8382140] - F Hayase, R H Nagaraj, S Miyata, F G Njoroge, V M Monnier. Aging of proteins: immunological detection of a glucose-derived pyrrole formed during maillard reaction in vivo.
The Journal of biological chemistry.
1989 Mar; 264(7):3758-64. doi:
10.1016/s0021-9258(19)84914-1. [PMID: 2917974]