Keratan (BioDeep_00000027686)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidic acid

化学式: C28H48N2O32S4 (1052.1072968)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)NC1C(CC(OC1OC2C(C(OC(C2O)OC3C(OC(C(C3O)NC(=O)C)OC4C(C(OC(C4O)O)COS(=O)(=O)O)O)COS(=O)(=O)O)COS(=O)(=O)O)O)COS(=O)(=O)O)O
InChI: InChI=1S/C28H48N2O32S4/c1-8(31)29-15-11(33)3-10(4-52-63(40,41)42)56-26(15)62-24-18(35)13(6-54-65(46,47)48)58-28(21(24)38)60-22-14(7-55-66(49,50)51)59-27(16(19(22)36)30-9(2)32)61-23-17(34)12(5-53-64(43,44)45)57-25(39)20(23)37/h10-28,33-39H,3-7H2,1-2H3,(H,29,31)(H,30,32)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t10-,11-,12+,13+,14+,15+,16+,17-,18-,19+,20+,21+,22+,23-,24-,25+,26-,27-,28-/m0/s1

描述信息

Keratan is a sulfated mucopolysaccharide initially isolated from bovine cornea. At least two types are known. Type I, found mostly in the cornea, contains D-galactose and D-glucosamine-6-O-sulfate as the repeating unit; type II, found in skeletal tissues, contains D-galactose and D-galactosamine-6-O-sulfate as the repeating unit.
A sulfated mucopolysaccharide initially isolated from bovine cornea. At least two types are known. Type I, found mostly in the cornea, contains D-galactose and D-glucosamine-6-O-sulfate as the repeating unit; type II, found in skeletal tissues, contains D-galactose and D-galactosamine-6-O-sulfate as the repeating unit. [HMDB]

同义名列表

16 个代谢物同义名

N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidic acid; N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidate; N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulfooxy)methyl]oxan-3-yl]ethanimidate; {[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxy}sulfonic acid; [(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxysulfonic acid; Keratan 6-sulphate; Keratan 6-sulfate; Kerato 6-sulphate; Keratan sulphate; Sulfate, keratan; Kerato 6-sulfate; Kerato sulphate; Keratan sulfate; Kerato sulfate; Keratosulfate; Keratan



数据库引用编号

6 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

  • Ru Chen, Weili Wang, Ronghua Yin, Ying Pan, Chen Xu, Na Gao, Xiaodong Luo, Jinhua Zhao. Structural Characterization and Anticoagulant Activities of a Keratan Sulfate-like Polysaccharide from the Sea Cucumber Holothuria fuscopunctata. Marine drugs. 2023 Dec; 21(12):. doi: 10.3390/md21120632. [PMID: 38132953]
  • H Hassani Lahsinoui, F Amraoui, L J A Spijkers, G J M Veenboer, S L M Peters, N van Vlies, L Vogt, C Ris-Stalpers, B J H van den Born, G B Afink. Soluble syndecan-1 and glycosaminoglycans in preeclamptic and normotensive pregnancies. Scientific reports. 2021 02; 11(1):4387. doi: 10.1038/s41598-021-82972-0. [PMID: 33623064]
  • Julie A D Van, Sergi Clotet-Freixas, Anne-Christin Hauschild, Ihor Batruch, Igor Jurisica, Yesmino Elia, Farid H Mahmud, Etienne Sochett, Eleftherios P Diamandis, James W Scholey, Ana Konvalinka. Urinary proteomics links keratan sulfate degradation and lysosomal enzymes to early type 1 diabetes. PloS one. 2020; 15(5):e0233639. doi: 10.1371/journal.pone.0233639. [PMID: 32453760]
  • Scott A Cameron, Olga V Zubkova, Steven Toms, Richard H Furneaux, Phillip M Rendle. Synthesis of 13 C-labelled sulfated N-acetyl-d-lactosamines to aid in the diagnosis of mucopolysaccharidosis diseases. Journal of labelled compounds & radiopharmaceuticals. 2019 02; 62(2):67-76. doi: 10.1002/jlcr.3697. [PMID: 30548247]
  • Hsiang-Yu Lin, Chung-Lin Lee, Yun-Ting Lo, Tuan-Jen Wang, Sung-Fa Huang, Tzu-Lin Chen, Yu-Shan Wang, Dau-Ming Niu, Chih-Kuang Chuang, Shuan-Pei Lin. The relationships between urinary glycosaminoglycan levels and phenotypes of mucopolysaccharidoses. Molecular genetics & genomic medicine. 2018 11; 6(6):982-992. doi: 10.1002/mgg3.471. [PMID: 30296009]
  • Shruti Aggarwal, Travis Peck, Jeffrey Golen, Zeynel A Karcioglu. Macular corneal dystrophy: A review. Survey of ophthalmology. 2018 Sep; 63(5):609-617. doi: 10.1016/j.survophthal.2018.03.004. [PMID: 29604391]
  • Hira Peracha, Kazuki Sawamoto, Lauren Averill, Heidi Kecskemethy, Mary Theroux, Mihir Thacker, Kyoko Nagao, Christian Pizarro, William Mackenzie, Hironori Kobayashi, Seiji Yamaguchi, Yasuyuki Suzuki, Kenji Orii, Tadao Orii, Toshiyuki Fukao, Shunji Tomatsu. Molecular genetics and metabolism, special edition: Diagnosis, diagnosis and prognosis of Mucopolysaccharidosis IVA. Molecular genetics and metabolism. 2018 09; 125(1-2):18-37. doi: 10.1016/j.ymgme.2018.05.004. [PMID: 29779902]
  • Shaukat A Khan, Robert W Mason, Roberto Giugliani, Kenji Orii, Toshiyuki Fukao, Yasuyuki Suzuki, Seiji Yamaguchi, Hironori Kobayashi, Tadao Orii, Shunji Tomatsu. Glycosaminoglycans analysis in blood and urine of patients with mucopolysaccharidosis. Molecular genetics and metabolism. 2018 09; 125(1-2):44-52. doi: 10.1016/j.ymgme.2018.04.011. [PMID: 29779903]
  • Christiane Auray-Blais, Jasmin Collerette-Tremblay, Pamela Lavoie. UPLC–MS/MS analysis of keratan sulfate from urine samples collected on filter paper for monitoring & follow-up of Morquio A patients. Bioanalysis. 2018 08; 10(15):1181-1192. doi: 10.4155/bio-2018-0064. [PMID: 30059256]
  • Qinying Li, Guoyun Li, Xiaoliang Zhao, Xindi Shan, Chao Cai, Jing Zhao, Fuming Zhang, Robert J Linhardt, Guangli Yu. Structural Characterization and Interaction with RCA120 of a Highly Sulfated Keratan Sulfate from Blue Shark (Prionace glauca) Cartilage. Marine drugs. 2018 Apr; 16(4):. doi: 10.3390/md16040128. [PMID: 29662015]
  • Abdellah Tebani, Isabelle Schmitz-Afonso, Lenaig Abily-Donval, Bénédicte Héron, Monique Piraud, Jérôme Ausseil, Anais Brassier, Pascale De Lonlay, Farid Zerimech, Frédéric M Vaz, Bruno J Gonzalez, Stephane Marret, Carlos Afonso, Soumeya Bekri. Urinary metabolic phenotyping of mucopolysaccharidosis type I combining untargeted and targeted strategies with data modeling. Clinica chimica acta; international journal of clinical chemistry. 2017 Dec; 475(?):7-14. doi: 10.1016/j.cca.2017.09.024. [PMID: 28982054]
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  • Christian J Hendriksz, Rossella Parini, Moeenaldeen D AlSayed, Julian Raiman, Roberto Giugliani, Martha L Solano Villarreal, John J Mitchell, Barbara K Burton, Norberto Guelbert, Fiona Stewart, Derralynn A Hughes, Kenneth I Berger, Peter Slasor, Robert Matousek, Elaina Jurecki, Adam J Shaywitz, Paul R Harmatz. Long-term endurance and safety of elosulfase alfa enzyme replacement therapy in patients with Morquio A syndrome. Molecular genetics and metabolism. 2016 09; 119(1-2):131-43. doi: 10.1016/j.ymgme.2016.05.018. [PMID: 27380995]
  • Ibrahim E Elsemman, Adil Mardinoglu, Saeed Shoaie, Taysir H Soliman, Jens Nielsen. Systems biology analysis of hepatitis C virus infection reveals the role of copy number increases in regions of chromosome 1q in hepatocellular carcinoma metabolism. Molecular bioSystems. 2016 04; 12(5):1496-506. doi: 10.1039/c5mb00827a. [PMID: 27040643]
  • Jill A Hadley, Maria Horvat-Gordon, Woo-Kyun Kim, Craig A Praul, Dennis Burns, Roland M Leach. Bone sialoprotein keratan sulfate proteoglycan (BSP-KSPG) and FGF-23 are important physiological components of medullary bone. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2016 Apr; 194(?):1-7. doi: 10.1016/j.cbpa.2015.12.009. [PMID: 26773479]
  • Christiane Auray-Blais, Pamela Lavoie, Bruno Maranda, Michel Boutin. Evaluation of urinary keratan sulfate disaccharides in MPS IVA patients using UPLC-MS/MS. Bioanalysis. 2016 Feb; 8(3):179-91. doi: 10.4155/bio.15.239. [PMID: 26805456]
  • Jasper J van Gemst, Markus A Loeven, Mark J J de Graaf, Jo H M Berden, Ton J Rabelink, Cornelis H Smit, Johan van der Vlag. RNA Contaminates Glycosaminoglycans Extracted from Cells and Tissues. PloS one. 2016; 11(11):e0167336. doi: 10.1371/journal.pone.0167336. [PMID: 27898729]
  • Joshua L Sloan, M Anisul Islam, Douglass F Jacobs. Reduced translocation of current photosynthate precedes changes in gas exchange for Quercus rubra seedlings under flooding stress. Tree physiology. 2016 Jan; 36(1):54-62. doi: 10.1093/treephys/tpv122. [PMID: 26655380]
  • Simon A Jones, Martin Bialer, Rossella Parini, Ken Martin, Hui Wang, Ke Yang, Adam J Shaywitz, Paul Harmatz. Safety and clinical activity of elosulfase alfa in pediatric patients with Morquio A syndrome (mucopolysaccharidosis IVA) less than 5 y. Pediatric research. 2015 Dec; 78(6):717-22. doi: 10.1038/pr.2015.169. [PMID: 26331768]
  • Barbara K Burton, Kenneth I Berger, Gregory D Lewis, Mark Tarnopolsky, Marsha Treadwell, John J Mitchell, Nicole Muschol, Simon A Jones, V Reid Sutton, Gregory M Pastores, Heather Lau, Rebecca Sparkes, Fred Genter, Adam J Shaywitz, Paul Harmatz. Safety and physiological effects of two different doses of elosulfase alfa in patients with morquio a syndrome: A randomized, double-blind, pilot study. American journal of medical genetics. Part A. 2015 Oct; 167A(10):2272-81. doi: 10.1002/ajmg.a.37172. [PMID: 26069231]
  • Darrell Pilling, Varsha Vakil, Nehemiah Cox, Richard H Gomer. TNF-α-stimulated fibroblasts secrete lumican to promote fibrocyte differentiation. Proceedings of the National Academy of Sciences of the United States of America. 2015 Sep; 112(38):11929-34. doi: 10.1073/pnas.1507387112. [PMID: 26351669]
  • Xiao-Mei Lu, Ling Ma, Yu-Nan Jin, Yan-Qiu Yu. Lumican overexpression exacerbates lipopolysaccharide-induced renal injury in mice. Molecular medicine reports. 2015 Sep; 12(3):4089-4094. doi: 10.3892/mmr.2015.3940. [PMID: 26081832]
  • Michael Steward, Yana Berezovskaya, Huiyu Zhou, Renée Shediac, Cynthia Sun, Nicole Miller, Phillip M Rendle. Recombinant, truncated B. circulans keratanase-II: Description and characterisation of a novel enzyme for use in measuring urinary keratan sulphate levels via LC-MS/MS in Morquio A syndrome. Clinical biochemistry. 2015 Aug; 48(12):796-802. doi: 10.1016/j.clinbiochem.2015.03.024. [PMID: 25866399]
  • Becky Schweighardt, Troy Tompkins, Kelly Lau, Lynne Jesaitis, Yulan Qi, Donald G Musson, Pamela Farmer, Christine Haller, Adam J Shaywitz, Ke Yang, Charles A O'Neill. Immunogenicity of Elosulfase Alfa, an Enzyme Replacement Therapy in Patients With Morquio A Syndrome: Results From MOR-004, a Phase III Trial. Clinical therapeutics. 2015 May; 37(5):1012-1021.e6. doi: 10.1016/j.clinthera.2014.11.005. [PMID: 25487082]
  • Ian W Hamley, Ashkan Dehsorkhi, Valeria Castelletto, Merlin N M Walter, Che J Connon, Mehedi Reza, Janne Ruokolainen. Self-Assembly and Collagen-Stimulating Activity of a Peptide Amphiphile Incorporating a Peptide Sequence from Lumican. Langmuir : the ACS journal of surfaces and colloids. 2015 Apr; 31(15):4490-5. doi: 10.1021/acs.langmuir.5b00057. [PMID: 25835126]
  • Katarzyna Winsz-Szczotka, Katarzyna Komosińska-Vassev, Kornelia Kuźnik-Trocha, Andrzej Siwiec, Bogusław Żegleń, Krystyna Olczyk. Circulating keratan sulfate as a marker of metabolic changes of cartilage proteoglycan in juvenile idiopathic arthritis; influence of growth factors as well as proteolytic and prooxidative agents on aggrecan alterations. Clinical chemistry and laboratory medicine. 2015 Feb; 53(2):291-7. doi: 10.1515/cclm-2014-0441. [PMID: 25153398]
  • Rocco Cappellesso, Renato Millioni, Giorgio Arrigoni, Francesca Simonato, Brasilina Caroccia, Elisabetta Iori, Vincenza Guzzardo, Laura Ventura, Paolo Tessari, Ambrogio Fassina. Lumican is overexpressed in lung adenocarcinoma pleural effusions. PloS one. 2015; 10(5):e0126458. doi: 10.1371/journal.pone.0126458. [PMID: 25961303]
  • Eveline J Langereis, Tom Wagemans, Wim Kulik, Dirk J Lefeber, Henk van Lenthe, Esmee Oussoren, Ans T van der Ploeg, George J Ruijter, Ron A Wevers, Frits A Wijburg, Naomi van Vlies. A Multiplex Assay for the Diagnosis of Mucopolysaccharidoses and Mucolipidoses. PloS one. 2015; 10(9):e0138622. doi: 10.1371/journal.pone.0138622. [PMID: 26406883]
  • Sayan Basu, Andrew J Hertsenberg, Martha L Funderburgh, Michael K Burrow, Mary M Mann, Yiqin Du, Kira L Lathrop, Fatima N Syed-Picard, Sheila M Adams, David E Birk, James L Funderburgh. Human limbal biopsy-derived stromal stem cells prevent corneal scarring. Science translational medicine. 2014 Dec; 6(266):266ra172. doi: 10.1126/scitranslmed.3009644. [PMID: 25504883]
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  • Susan Y Ritter, Jamie Collins, Bryan Krastins, David Sarracino, Mary Lopez, Elena Losina, Antonios O Aliprantis. Mass spectrometry assays of plasma biomarkers to predict radiographic progression of knee osteoarthritis. Arthritis research & therapy. 2014 Oct; 16(5):456. doi: 10.1186/s13075-014-0456-6. [PMID: 25287745]
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  • Dorota Maszczak-Seneczko, Paulina Sosicka, Teresa Olczak, Piotr Jakimowicz, Michał Majkowski, Mariusz Olczak. UDP-N-acetylglucosamine transporter (SLC35A3) regulates biosynthesis of highly branched N-glycans and keratan sulfate. The Journal of biological chemistry. 2013 Jul; 288(30):21850-60. doi: 10.1074/jbc.m113.460543. [PMID: 23766508]
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