Isodesmosine (BioDeep_00000027641)
human metabolite Endogenous blood metabolite
代谢物信息卡片
2-Amino-6-[3,5-bis(3-amino-4-hydroxy-4-oxobutyl)-2-(4-amino-5-hydroxy-5-oxopentyl)pyridin-1-ium-1-yl]hexanoic acid
化学式: C24H40N5O8+ (526.287674)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 3.03%
分子结构信息
SMILES: C1=C(C=[N+](C(=C1CCC(C(=O)O)N)CCCC(C(=O)O)N)CCCCC(C(=O)O)N)CCC(C(=O)O)N
InChI: InChI=1S/C24H39N5O8/c25-16(21(30)31)4-1-2-11-29-13-14(7-9-18(27)23(34)35)12-15(8-10-19(28)24(36)37)20(29)6-3-5-17(26)22(32)33/h12-13,16-19H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1
描述信息
2-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium. A rare amino acid found in elastin, formed by condensation of four molecules of lysine into a pyridinium ring.
Degradation production of Elastin which, together with Desmosine
同义名列表
8 个代谢物同义名
2-Amino-6-[3,5-bis(3-amino-4-hydroxy-4-oxobutyl)-2-(4-amino-5-hydroxy-5-oxopentyl)pyridin-1-ium-1-yl]hexanoic acid; 2-Amino-6-[3,5-bis(3-amino-4-hydroxy-4-oxobutyl)-2-(4-amino-5-hydroxy-5-oxopentyl)pyridin-1-ium-1-yl]hexanoate; 3,5-bis(3-amino-3-carboxypropyl)-2-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium; 2-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)-pyridinium; 2-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium; Iso-desmosin; Isodesmosine; Ide
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:64366
- PubChem: 13811
- HMDB: HMDB0000739
- Wikipedia: Isodesmosine
- MeSH: Isodesmosine
- foodb: FDB000467
- chemspider: 13214
- CAS: 991-01-5
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
- Gerard M Turino. Chronic Obstructive Pulmonary Disease. A Biomarker and a Potential Therapy.
Annals of the American Thoracic Society.
2018 02; 15(Suppl 1):S15-S17. doi:
10.1513/annalsats.201707-568kv. [PMID: 29461896] - Changhwan Kim, Yousang Ko, Su Hee Kim, Hyun Ju Yoo, Jae Seung Lee, Chin Kook Rhee, Jin Hwa Lee, Ji-Hyun Lee, Tae-Hyung Kim, Seong Yong Lim, Kwang Ha Yoo, Joon Beom Seo, Yeon-Mok Oh, Sang-Do Lee, Yong Bum Park. Urinary desmosine is associated with emphysema severity and frequent exacerbation in patients with COPD.
Respirology (Carlton, Vic.).
2018 02; 23(2):176-181. doi:
10.1111/resp.13170. [PMID: 28905464] - Rob Janssen, Cees Vermeer. Vitamin K deficit and elastolysis theory in pulmonary elasto-degenerative diseases.
Medical hypotheses.
2017 Oct; 108(?):38-41. doi:
10.1016/j.mehy.2017.07.029. [PMID: 29055397] - Amin Sagar, Ehtesham Arif, Ashish Kumar Solanki, Pankaj Srivastava, Michael G Janech, Seok-Hyung Kim, Joshua H Lipschutz, Sang-Ho Kwon, Ashish, Deepak Nihalani. Targeting Neph1 and ZO-1 protein-protein interaction in podocytes prevents podocyte injury and preserves glomerular filtration function.
Scientific reports.
2017 09; 7(1):12047. doi:
10.1038/s41598-017-12134-8. [PMID: 28935902] - Ruth Minkin, Gagangeet Sandhu, Horiana Grosu, Lori Tartell, Shuren Ma, Yong Y Lin, Edward Eden, Gerard M Turino. Desmosine and Isodesmosine as a Novel Biomarker for Pulmonary Arterial Hypertension: A Pilot Study.
American journal of therapeutics.
2017 Jul; 24(4):e399-e404. doi:
10.1097/mjt.0000000000000260. [PMID: 26237301] - Jerome Cantor, Shuren Ma, Gerard Turino. A pilot clinical trial to determine the safety and efficacy of aerosolized hyaluronan as a treatment for COPD.
International journal of chronic obstructive pulmonary disease.
2017; 12(?):2747-2752. doi:
10.2147/copd.s142156. [PMID: 29075107] - Xingjian Liu, Shuren Ma, Sophie Liu, Ming Liu, Gerard Turino, Jerome Cantor. The Ratio of Free to Bound Desmosine and Isodesmosine May Reflect Emphysematous Changes in COPD.
Lung.
2015 Jun; 193(3):329-34. doi:
10.1007/s00408-015-9712-z. [PMID: 25762453] - Sara Ongay, Gert Hendriks, Jos Hermans, Maarten van den Berge, Nick H T ten Hacken, Nico C van de Merbel, Rainer Bischoff. Quantification of free and total desmosine and isodesmosine in human urine by liquid chromatography tandem mass spectrometry: a comparison of the surrogate-analyte and the surrogate-matrix approach for quantitation.
Journal of chromatography. A.
2014 Jan; 1326(?):13-9. doi:
10.1016/j.chroma.2013.12.035. [PMID: 24380655] - Osama Albarbarawi, Alun Barton, Douglas Miller, Charles McSharry, Rekha Chaudhuri, Neil C Thomson, Colin Na Palmer, Graham Devereux, Jeffrey T-J Huang. Characterization and validation of an isotope-dilution LC-MS/MS method for quantification of total desmosine and isodesmosine in plasma and serum.
Bioanalysis.
2013 Aug; 5(16):1991-2001. doi:
10.4155/bio.13.164. [PMID: 23937134] - Shuren Ma, Yong Y Lin, Jiangtao He, Farshid N Rouhani, Mark Brantly, Gerard M Turino. Alpha-1 antitrypsin augmentation therapy and biomarkers of elastin degradation.
COPD.
2013 Aug; 10(4):473-81. doi:
10.3109/15412555.2013.771163. [PMID: 23560990] - Jens Lamerz, Arno Friedlein, Nicole Soder, Paul Cutler, Heinz Döbeli. Determination of free desmosine in human plasma and its application in two experimental medicine studies.
Analytical biochemistry.
2013 May; 436(2):127-36. doi:
10.1016/j.ab.2013.01.012. [PMID: 23399390] - William MacNee. Systemic inflammatory biomarkers and co-morbidities of chronic obstructive pulmonary disease.
Annals of medicine.
2013 May; 45(3):291-300. doi:
10.3109/07853890.2012.732703. [PMID: 23110517] - Atsushi Miyajima, Masahiro Okamoto, Takafumi Muto, Takashi Hirota. Disruption of elastic lamellae in aorta and dysfunction of vaso-regulation by rofecoxib in rats.
The Journal of toxicological sciences.
2013; 38(5):719-29. doi:
10.2131/jts.38.719. [PMID: 24025789] - C A Lindberg, G Engström, M Gerhardsson de Verdier, U Nihlén, M Anderson, K Forsman-Semb, M Svartengren. Total desmosines in plasma and urine correlate with lung function.
The European respiratory journal.
2012 Apr; 39(4):839-45. doi:
10.1183/09031936.00064611. [PMID: 21965222] - M Luisetti, J Stolk, P Iadarola. Desmosine, a biomarker for COPD: old and in the way.
The European respiratory journal.
2012 Apr; 39(4):797-8. doi:
10.1183/09031936.00172911. [PMID: 22467719] - Stefan Röpcke, Olaf Holz, Gereon Lauer, Meike Müller, Susanne Rittinghausen, Peter Ernst, Gezim Lahu, Martin Elmlinger, Norbert Krug, Jens M Hohlfeld. Repeatability of and relationship between potential COPD biomarkers in bronchoalveolar lavage, bronchial biopsies, serum, and induced sputum.
PloS one.
2012; 7(10):e46207. doi:
10.1371/journal.pone.0046207. [PMID: 23056262] - Neil A Devenport, James C Reynolds, Ved Parkash, Jason Cook, Daniel J Weston, Colin S Creaser. Determination of free desmosine and isodesmosine as urinary biomarkers of lung disorder using ultra performance liquid chromatography-ion mobility-mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Dec; 879(32):3797-801. doi:
10.1016/j.jchromb.2011.10.016. [PMID: 22088351] - Laura Fregonese, Fabio Ferrari, Marco Fumagalli, Maurizio Luisetti, Jan Stolk, Paolo Iadarola. Long-term variability of desmosine/isodesmosine as biomarker in alpha-1-antritrypsin deficiency-related COPD.
COPD.
2011 Oct; 8(5):329-33. doi:
10.3109/15412555.2011.589871. [PMID: 21793711] - Natalie Slowik, Shuren Ma, Jiangtao He, Yong Y Lin, Offie P Soldin, Richard A Robbins, Gerard M Turino. The effect of secondhand smoke exposure on markers of elastin degradation.
Chest.
2011 Oct; 140(4):946-953. doi:
10.1378/chest.10-2298. [PMID: 21415130] - Gerard M Turino, Shuren Ma, Yong Y Lin, Jerome O Cantor, Maurizio Luisetti. Matrix elastin: a promising biomarker for chronic obstructive pulmonary disease.
American journal of respiratory and critical care medicine.
2011 Sep; 184(6):637-41. doi:
10.1164/rccm.201103-0450pp. [PMID: 21757624] - Shuren Ma, Gerard M Turino, Yong Y Lin. Quantitation of desmosine and isodesmosine in urine, plasma, and sputum by LC-MS/MS as biomarkers for elastin degradation.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Jul; 879(21):1893-8. doi:
10.1016/j.jchromb.2011.05.011. [PMID: 21621489] - Martina Ulrich, Dieter Worlitzsch, Simona Viglio, Nanna Siegmann, Paolo Iadarola, Janis K Shute, Marianne Geiser, Gerald B Pier, Godehard Friedel, Mark L Barr, Antje Schuster, Keith C Meyer, Felix Ratjen, Thomas Bjarnsholt, Erich Gulbins, Gerd Döring. Alveolar inflammation in cystic fibrosis.
Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society.
2010 May; 9(3):217-27. doi:
10.1016/j.jcf.2010.03.001. [PMID: 20347403] - Osama Albarbarawi, Alun Barton, Zhaosheng Lin, Eddie Takahashi, Ajay Buddharaju, Jeffrey Brady, Douglas Miller, Colin N A Palmer, Jeffrey T-J Huang. Measurement of urinary total desmosine and isodesmosine using isotope-dilution liquid chromatography-tandem mass spectrometry.
Analytical chemistry.
2010 May; 82(9):3745-50. doi:
10.1021/ac100152f. [PMID: 20361748] - Kohei Shiraishi, Kazue Matsuzaki, Akinori Matsumoto, Yuuki Hashimoto, Kazuhiko Iba. Development of a robust LC-MS/MS method for determination of desmosine and isodesmosine in human urine.
Journal of oleo science.
2010; 59(8):431-9. doi:
10.5650/jos.59.431. [PMID: 20625235] - Michel Boutin, Carl Berthelette, François G Gervais, Mary-Beth Scholand, John Hoidal, Mark F Leppert, Kevin P Bateman, Pierre Thibault. High-sensitivity nanoLC-MS/MS analysis of urinary desmosine and isodesmosine.
Analytical chemistry.
2009 Mar; 81(5):1881-7. doi:
10.1021/ac801745d. [PMID: 19178285] - Shuren Ma, Yong Y Lin, Lori Tartell, Gerard M Turino. The effect of tiotropium therapy on markers of elastin degradation in COPD.
Respiratory research.
2009 Feb; 10(?):12. doi:
10.1186/1465-9921-10-12. [PMID: 19243601] - M Luisetti, S Ma, P Iadarola, P J Stone, S Viglio, B Casado, Y Y Lin, G L Snider, G M Turino. Desmosine as a biomarker of elastin degradation in COPD: current status and future directions.
The European respiratory journal.
2008 Nov; 32(5):1146-57. doi:
10.1183/09031936.00174807. [PMID: 18978133] - Shuren Ma, Yong Y Lin, Gerard M Turino. Measurements of desmosine and isodesmosine by mass spectrometry in COPD.
Chest.
2007 May; 131(5):1363-71. doi:
10.1378/chest.06-2251. [PMID: 17494786] - Semra Koçtürk, Gülgün Oktay, Gül Güner, Cetin Pekçetin, Ataman Güre. Effect of D-penicillamine on rat lung elastin cross-linking during the perinatal period.
Cell biochemistry and function.
2006 Mar; 24(2):167-72. doi:
10.1002/cbf.1209. [PMID: 15657943] - Shuren Ma, Seymour Lieberman, Gerard M Turino, Yong Y Lin. The detection and quantitation of free desmosine and isodesmosine in human urine and their peptide-bound forms in sputum.
Proceedings of the National Academy of Sciences of the United States of America.
2003 Oct; 100(22):12941-3. doi:
10.1073/pnas.2235344100. [PMID: 14563926] - P J Stone. Potential use of collagen and elastin degradation markers for monitoring liver fibrosis in schistosomiasis.
Acta tropica.
2000 Oct; 77(1):97-9. doi:
10.1016/s0001-706x(00)00118-2. [PMID: 10996125] - S Viglio, P Iadarola, A Lupi, R Trisolini, C Tinelli, B Balbi, V Grassi, D Worlitzsch, G Döring, F Meloni, K C Meyer, L Dowson, S L Hill, R A Stockley, M Luisetti. MEKC of desmosine and isodesmosine in urine of chronic destructive lung disease patients.
The European respiratory journal.
2000 Jun; 15(6):1039-45. doi:
10.1034/j.1399-3003.2000.01511.x. [PMID: 10885422] - D C Bode, E D Pagani, W R Cumiskey, R von Roemeling, L Hamel, P J Silver. Comparison of urinary desmosine excretion in patients with chronic obstructive pulmonary disease or cystic fibrosis.
Pulmonary pharmacology & therapeutics.
2000; 13(4):175-80. doi:
10.1006/pupt.2000.0245. [PMID: 10930356] - S Viglio, G Zanaboni, M Luisetti, R Trisolini, R Grimm, G Cetta, P Iadarola. Micellar electrokinetic chromatography for the determination of urinary desmosine and isodesmosine in patients affected by chronic obstructive pulmonary disease.
Journal of chromatography. B, Biomedical sciences and applications.
1998 Aug; 714(1):87-98. doi:
10.1016/s0378-4347(98)00046-2. [PMID: 9746238] - P J Stone, A Beiser, D J Gottlieb. Circadian variation of urinary excretion of elastin and collagen crosslinks.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.).
1998 Jul; 218(3):229-33. doi:
10.3181/00379727-218-44291. [PMID: 9648941] - P J Stone, E C Lucey, G L Snider, C Franzblau. Distribution of elastin in hamsters and the turnover rates of different elastin pools.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.).
1997 May; 215(1):94-101. doi:
10.3181/00379727-215-44118. [PMID: 9142143] - P J Stone, M W Konstan, M Berger, H L Dorkin, C Franzblau, G L Snider. Elastin and collagen degradation products in urine of patients with cystic fibrosis.
American journal of respiratory and critical care medicine.
1995 Jul; 152(1):157-62. doi:
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Journal of chromatography. B, Biomedical applications.
1995 Jun; 668(2):199-207. doi:
10.1016/0378-4347(95)00092-w. [PMID: 7581855] - P J Stone, J H Korn, H North, E V Lally, L C Miller, L B Tucker, S Strongwater, G L Snider, C Franzblau. Cross-linked elastin and collagen degradation products in the urine of patients with scleroderma.
Arthritis and rheumatism.
1995 Apr; 38(4):517-24. doi:
10.1002/art.1780380409. [PMID: 7718005] - P J Stone, D J Gottlieb, G T O'Connor, D E Ciccolella, R Breuer, J Bryan-Rhadfi, H A Shaw, C Franzblau, G L Snider. Elastin and collagen degradation products in urine of smokers with and without chronic obstructive pulmonary disease.
American journal of respiratory and critical care medicine.
1995 Apr; 151(4):952-9. doi:
10.1164/ajrccm.151.4.7697272. [PMID: 7697272] - P J Stone, T A Morris, C Franzblau, G L Snider. Preliminary evidence that augmentation therapy diminishes degradation of cross-linked elastin in alpha-1-antitrypsin-deficient humans.
Respiration; international review of thoracic diseases.
1995; 62(2):76-9. doi:
10.1159/000196395. [PMID: 7784713] - P J Stone, E C Lucey, G L Snider, C Franzblau. Effect of diet on urinary excretion of desmosine and hydroxylysyl pyridinoline.
American journal of respiratory and critical care medicine.
1994 Jan; 149(1):174-7. doi:
10.1164/ajrccm.149.1.8111578. [PMID: 8111578] - P J Stone, J Bryan-Rhadfi, E C Lucey, D E Ciccolella, G Crombie, B Faris, G L Snider, C Franzblau. Measurement of urinary desmosine by isotope dilution and high performance liquid chromatography. Correlation between elastase-induced air-space enlargement in the hamster and elevation of urinary desmosine.
The American review of respiratory disease.
1991 Aug; 144(2):284-90. doi:
10.1164/ajrccm/144.2.284. [PMID: 1859049] - T Watanabe, K Ishimori, A J Verplanke, H Matsuki, H Kasuga. An enzyme-linked immunosorbent assay (ELISA) for the quantitation of urinary desmosine.
The Tokai journal of experimental and clinical medicine.
1989 Sep; 14(4):347-56. doi:
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1985 Apr; 131(4):568-72. doi:
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The Journal of laboratory and clinical medicine.
1979 Dec; 94(6):848-52. doi:
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