N-Glycolylneuraminic acid (BioDeep_00000001689)
Secondary id: BioDeep_00000055117, BioDeep_00000594102
human metabolite Endogenous
代谢物信息卡片
(2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
化学式: C11H19NO10 (325.1009)
中文名称: N-羟乙酰神经氨酸
谱图信息:
最多检出来源 Homo sapiens(otcml) 5.94%
分子结构信息
SMILES: C1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)NC(=O)CO)O
InChI: InChI=1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)
描述信息
N-Glycolylneuraminic acid (Neu5Gc) is a widely expressed sialic acid found in most mammalian cells. Although humans are genetically deficient in producing Neu5Gc, small amounts are present in human cells and biofluids. Humans cannot synthesize Neu5Gc because the human gene CMAH is irreversibly mutated, though it is found in apes. This loss of the CMAH gene was estimated to have occurred two to three million years ago, just before the emergence of the genus Homo. A dietary origin of Neu5Gc was suggested by human volunteer studies. These trace amounts of Neu5Gc were determined to come from the consumption of animals in the human diet (i.e. red meats such as lamb, pork, and beef). Neu5Gc can also be found in dairy products, but to a lesser extent. Neu5Gc is not found in poultry and is found in only trace amounts in fish (Wikipedia).
Isolated from beef serum
KEIO_ID G062
同义名列表
29 个代谢物同义名
(2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid; 3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonic acid; 3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonate; N-Glycolylneuraminic acid, (alpha-D-gal)-isomer; N-Glycolyl-beta-neuraminic acid; N-Glycoloyl-b-neuraminic acid; N-Glycoloyl-β-neuraminic acid; N-Glycoloyl-beta-neuraminate; N-Glycolyl-β-neuraminic acid; N-Glycolyl-5-neuraminic acid; N-Glycolyl-b-neuraminic acid; N-Glycolyl-beta-neuraminate; N-Glycoloylneuraminic acid; N-Glycolyl-Neuraminic acid; N-Glycoloyl-b-neuraminate; N-Glycoloyl-β-neuraminate; N-Glycolylneuraminic acid; N-Glycolyl-b-neuraminate; N-Glycolyl-β-neuraminate; N-Glycolyl-5-neuraminate; N-Glycoloyl-neuraminate; N-Glycoloylneuraminate; N-Glycolylneuraminate; NeuGc;GcNeu; Neu5GC; GcNeu; NeuGc; NGNA; NeuNGc
数据库引用编号
31 个数据库交叉引用编号
- ChEBI: CHEBI:146193
- ChEBI: CHEBI:62084
- KEGG: C03410
- PubChem: 4603312
- PubChem: 123802
- PubChem: 440001
- HMDB: HMDB0000833
- Metlin: METLIN63227
- ChEMBL: CHEMBL496421
- Wikipedia: N-Glycolylneuraminic_acid
- foodb: FDB001165
- chemspider: 110352
- CAS: 885329-49-7
- CAS: 1113-83-3
- MoNA: KO000911
- MoNA: KO003009
- MoNA: KO003010
- MoNA: KO003012
- MoNA: KO000909
- MoNA: KO003013
- MoNA: KO000910
- MoNA: KO000912
- MoNA: KO000908
- MoNA: KO003011
- PMhub: MS000000988
- PubChem: 6239
- PDB-CCD: NGC
- PDB-CCD: NGE
- 3DMET: B04895
- NIKKAJI: J2.742.226H
- RefMet: N-Glycolylneuraminic acid
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(1)
- Aminosugars metabolism ( Aminosugars metabolism ):
D-Fructose 6-phosphate + NH3 ⟶ D-Glucosamine 6-phosphate + H2O
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
3 个相关的物种来源信息
- 8296 - Ambystoma mexicanum: 10.3389/FCELL.2020.562940
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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
- Yu-An Annie Chien, Brynn K Alford, Brian R Wasik, Wendy S Weichert, Colin R Parrish, Susan Daniel. Single Particle Analysis of H3N2 Influenza Entry Differentiates the Impact of the Sialic Acids (Neu5Ac and Neu5Gc) on Virus Binding and Membrane Fusion.
Journal of virology.
2023 Feb; ?(?):e0146322. doi:
10.1128/jvi.01463-22. [PMID: 36779754] - Lucy K Shewell, Christopher J Day, Jamie R Kutasovic, Jodie L Abrahams, Jing Wang, Jessica Poole, Colleen Niland, Kaltin Ferguson, Jodi M Saunus, Sunil R Lakhani, Mark von Itzstein, James C Paton, Adrienne W Paton, Michael P Jennings. N-glycolylneuraminic acid serum biomarker levels are elevated in breast cancer patients at all stages of disease.
BMC cancer.
2022 Mar; 22(1):334. doi:
10.1186/s12885-022-09428-0. [PMID: 35346112] - Haneulnari Lee, Eun Mi Park, Nayoung Ko, Kimyung Choi, Keon Bong Oh, Hee Jung Kang. Effect of Factor H on Complement Alternative Pathway Activation in Human Serum Remains on Porcine Cells Lacking N-Glycolylneuraminic Acid.
Frontiers in immunology.
2022; 13(?):859261. doi:
10.3389/fimmu.2022.859261. [PMID: 35444661] - Paul T Martin, Kunio Kawanishi, Anna Ashbrook, Bethannie Golden, Annie Samraj, Kelly E Crowe, Deborah A Zygmunt, Jonathan Okerblom, Hai Yu, Agatha Maki, Sandra Diaz, Xi Chen, Paul M L Janssen, Ajit Varki. Serum Antibodies to N-Glycolylneuraminic Acid Are Elevated in Duchenne Muscular Dystrophy and Correlate with Increased Disease Pathology in Cmah-/-mdx Mice.
The American journal of pathology.
2021 08; 191(8):1474-1486. doi:
10.1016/j.ajpath.2021.04.015. [PMID: 34294193] - Hayato Iwase, Abhijit Jagdale, Takayuki Yamamoto, Mohamed H Bikhet, Huy Q Nguyen, Mohamed Ezzelarab, David Ayares, Douglas J Anderson, Devin E Eckhoff, Jeremy B Foote, Huma Fatima, Hendrik Jan Schuurman, Hidetaka Hara, David K C Cooper. Evidence suggesting that deletion of expression of N-glycolylneuraminic acid (Neu5Gc) in the organ-source pig is associated with increased antibody-mediated rejection of kidney transplants in baboons.
Xenotransplantation.
2021 07; 28(4):e12700. doi:
10.1111/xen.12700. [PMID: 34036638] - Eun Jin Lee, Haneulnari Lee, Eun Mi Park, Hee Jung Kang, Sang Joon Kim, Chung-Gyu Park. Immunoglobulin M and Immunoglobulin G Subclass Distribution of Anti-galactose-Alpha-1,3-Galactose and Anti-N-Glycolylneuraminic Acid Antibodies in Healthy Korean Adults.
Transplantation proceedings.
2021 Jun; 53(5):1762-1770. doi:
10.1016/j.transproceed.2021.01.011. [PMID: 33581850] - Y Y Zhuang, H Y Zheng, H Lan, H W Li. [Study on the correlation between dietary N-glycolylneuraminic acid intake and chronic inflammation state of body].
Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine].
2020 Jun; 54(6):668-672. doi:
10.3760/cma.j.cn112150-20191021-00802. [PMID: 32842284] - Kayluz F Boligan, Johanna Oechtering, Christian W Keller, Benjamin Peschke, Robert Rieben, Nicolai Bovin, Ludwig Kappos, Richard D Cummings, Jens Kuhle, Stephan von Gunten, Jan D Lünemann. Xenogeneic Neu5Gc and self-glycan Neu5Ac epitopes are potential immune targets in MS.
Neurology(R) neuroimmunology & neuroinflammation.
2020 03; 7(2):. doi:
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Frontiers in immunology.
2020 ; 11(?):1480. doi:
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Nature microbiology.
2019 12; 4(12):2082-2089. doi:
10.1038/s41564-019-0564-9. [PMID: 31548686] - Hongying Li, Rui Chang, Qiujin Zhu, Xuling Zhu, Aqi Xu, Yingzi Zhou, Yinxue Yan. [Effects of genistein on N-glycolylneuraminic acid content in rats and the interaction with sialyl transferase].
Sheng wu gong cheng xue bao = Chinese journal of biotechnology.
2019 May; 35(5):857-870. doi:
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European journal of clinical investigation.
2019 Apr; 49(4):e13069. doi:
10.1111/eci.13069. [PMID: 30620396] - Kwon-Ho Song, Choong-Hwan Kwak, Tae-Wook Chung, Sun-Hyung Ha, Jun-Young Park, Ki-Tae Ha, Seung-Hak Cho, Young-Choon Lee, Cheorl-Ho Kim. Intestine specific regulation of pig cytidine-5'-monophospho-N-acetylneuraminic acid hydroxylase gene for N-glycolylneuraminic acid biosynthesis.
Scientific reports.
2019 03; 9(1):4292. doi:
10.1038/s41598-019-40522-9. [PMID: 30862964] - Salam Bashir, Shani Leviatan Ben Arye, Eliran Moshe Reuven, Hai Yu, Cristina Costa, Manuel Galiñanes, Tomaso Bottio, Xi Chen, Vered Padler-Karavani. Presentation Mode of Glycans Affect Recognition of Human Serum anti-Neu5Gc IgG Antibodies.
Bioconjugate chemistry.
2019 01; 30(1):161-168. doi:
10.1021/acs.bioconjchem.8b00817. [PMID: 30500162] - Andrea Perota, Cesare Galli. N-Glycolylneuraminic Acid (Neu5Gc) Null Large Animals by Targeting the CMP-Neu5Gc Hydroxylase (CMAH).
Frontiers in immunology.
2019; 10(?):2396. doi:
10.3389/fimmu.2019.02396. [PMID: 31681287] - L K Shewell, J J Wang, J C Paton, A W Paton, C J Day, M P Jennings. Detection of N-glycolylneuraminic acid biomarkers in sera from patients with ovarian cancer using an engineered N-glycolylneuraminic acid-specific lectin SubB2M.
Biochemical and biophysical research communications.
2018 12; 507(1-4):173-177. doi:
10.1016/j.bbrc.2018.11.001. [PMID: 30415777] - Sheng Gong, Honglin Ren, Chao Lin, Pan Hu, Ruiyun Tian, Zengshan Liu, Yansong Li, Yu Zhou, Yong Yang, Shiying Lu. Immunochromatographic strip biosensor for the rapid detection of N-glycolylneuraminic acid based on aptamer-conjugated nanoparticle.
Analytical biochemistry.
2018 11; 561-562(?):52-58. doi:
10.1016/j.ab.2018.07.017. [PMID: 30036498] - Jing Wang, Lucy K Shewell, Adrienne W Paton, James C Paton, Christopher J Day, Michael P Jennings. Specificity and utility of SubB2M, a new N-glycolylneuraminic acid lectin.
Biochemical and biophysical research communications.
2018 06; 500(3):765-771. doi:
10.1016/j.bbrc.2018.04.151. [PMID: 29684349] - Annie N Samraj, Kimberly A Bertrand, Robert Luben, Zahra Khedri, Hai Yu, Dzung Nguyen, Christopher J Gregg, Sandra L Diaz, Sherilyn Sawyer, Xi Chen, Heather Eliassen, Vered Padler-Karavani, Kana Wu, Kay-Tee Khaw, Walter Willett, Ajit Varki. Polyclonal human antibodies against glycans bearing red meat-derived non-human sialic acid N-glycolylneuraminic acid are stable, reproducible, complex and vary between individuals: Total antibody levels are associated with colorectal cancer risk.
PloS one.
2018; 13(6):e0197464. doi:
10.1371/journal.pone.0197464. [PMID: 29912879] - Christopher J Day, Adrienne W Paton, Melanie A Higgins, Lucy K Shewell, Freda E-C Jen, Benjamin L Schulz, Brock P Herdman, James C Paton, Michael P Jennings. Structure aided design of a Neu5Gc specific lectin.
Scientific reports.
2017 05; 7(1):1495. doi:
10.1038/s41598-017-01522-9. [PMID: 28473713] - Bingsi Gao, Cassandra Long, Whayoung Lee, Zhongqiang Zhang, Xiaotian Gao, Doug Landsittel, Mohamed Ezzelarab, David Ayares, Yuliang Huang, David K C Cooper, Yi Wang, Hidetaka Hara. Anti-Neu5Gc and anti-non-Neu5Gc antibodies in healthy humans.
PloS one.
2017; 12(7):e0180768. doi:
10.1371/journal.pone.0180768. [PMID: 28715486] - Kwon-Ho Song, Choong-Hwan Kwak, Un-Ho Jin, Sun-Hyung Ha, Jun-Young Park, Fukushi Abekura, Young-Chae Chang, Seung-Hak Cho, Kichoon Lee, Tae-Wook Chung, Ki-Tae Ha, Young-Choon Lee, Cheorl-Ho Kim. Housekeeping promoter 5'pcmah-2 of pig CMP-N-acetylneuraminic acid hydroxylase gene for NeuGc expression.
Glycoconjugate journal.
2016 10; 33(5):779-88. doi:
10.1007/s10719-016-9671-5. [PMID: 27188588] - Sunghoon Hurh, Bohae Kang, Inho Choi, Bumrae Cho, Eun Mi Lee, Hwajung Kim, Young June Kim, Yun Shin Chung, Jong Cheol Jeong, Jong-Ik Hwang, Jae Young Kim, Byeong Chun Lee, Charles D Surh, Jaeseok Yang, Curie Ahn. Human antibody reactivity against xenogeneic N-glycolylneuraminic acid and galactose-α-1,3-galactose antigen.
Xenotransplantation.
2016 07; 23(4):279-92. doi:
10.1111/xen.12239. [PMID: 27373998] - Whayoung Lee, Hidetaka Hara, Mohamed B Ezzelarab, Hayato Iwase, Rita Bottino, Cassandra Long, Jagdeece Ramsoondar, David Ayares, David K C Cooper. Initial in vitro studies on tissues and cells from GTKO/CD46/NeuGcKO pigs.
Xenotransplantation.
2016 03; 23(2):137-50. doi:
10.1111/xen.12229. [PMID: 26988899] - Paul G Lopez, Lauren Girard, Marjorie Buist, Andrey Giovanni Gomes de Oliveira, Edward Bodnar, Apolline Salama, Jean-Paul Soulillou, Hélène Perreault. Characterization of N-glycosylation and amino acid sequence features of immunoglobulins from swine.
Glycoconjugate journal.
2016 Feb; 33(1):79-91. doi:
10.1007/s10719-015-9637-z. [PMID: 26586247] - Wei-Na Gao, Lee-Fong Yau, Liang Liu, Xing Zeng, Da-Can Chen, Min Jiang, Ju Liu, Jing-Rong Wang, Zhi-Hong Jiang. Microfluidic Chip-LC/MS-based Glycomic Analysis Revealed Distinct N-glycan Profile of Rat Serum.
Scientific reports.
2015 Aug; 5(?):12844. doi:
10.1038/srep12844. [PMID: 26248949] - Risa Taguchi, Akira Minami, Yukino Matsuda, Tadanobu Takahashi, Tadamune Otsubo, Kiyoshi Ikeda, Takashi Suzuki. Preferential Accumulation of 14C-N-Glycolylneuraminic Acid over 14C-N-Acetylneuraminic Acid in the Rat Brain after Tail Vein Injection.
PloS one.
2015; 10(6):e0131061. doi:
10.1371/journal.pone.0131061. [PMID: 26098915] - Tadanobu Takahashi, Maiko Takano, Yuuki Kurebayashi, Midori Masuda, Sawako Kawagishi, Masahiro Takaguchi, Takashi Yamanaka, Akira Minami, Tadamune Otsubo, Kiyoshi Ikeda, Takashi Suzuki. N-glycolylneuraminic acid on human epithelial cells prevents entry of influenza A viruses that possess N-glycolylneuraminic acid binding ability.
Journal of virology.
2014 Aug; 88(15):8445-56. doi:
10.1128/jvi.00716-14. [PMID: 24829344] - F Priego-Capote, M I Orozco-Solano, M Calderón-Santiago, M D Luque de Castro. Quantitative determination and confirmatory analysis of N-acetylneuraminic and N-glycolylneuraminic acids in serum and urine by solid-phase extraction on-line coupled to liquid chromatography-tandem mass spectrometry.
Journal of chromatography. A.
2014 Jun; 1346(?):88-96. doi:
10.1016/j.chroma.2014.04.051. [PMID: 24800968] - David Cohen, Yuko Miyagawa, Ruhina Mehra, Whayoung Lee, Kumiko Isse, Cassandra Long, David L Ayares, David K C Cooper, Hidetaka Hara. Distribution of non-gal antigens in pig cornea: relevance to corneal xenotransplantation.
Cornea.
2014 Apr; 33(4):390-7. doi:
10.1097/ico.0000000000000069. [PMID: 24488129] - Yue Chen, Lili Pan, Ni Liu, Frederic A Troy, Bing Wang. LC-MS/MS quantification of N-acetylneuraminic acid, N-glycolylneuraminic acid and ketodeoxynonulosonic acid levels in the urine and potential relationship with dietary sialic acid intake and disease in 3- to 5-year-old children.
The British journal of nutrition.
2014 Jan; 111(2):332-41. doi:
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PloS one.
2013; 8(8):e71159. doi:
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Biochimica et biophysica acta.
2012 Sep; 1820(9):1444-55. doi:
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Cellular reprogramming.
2012 Aug; 14(4):353-63. doi:
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BMC clinical pharmacology.
2011 Nov; 11(?):17. doi:
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The Journal of biological chemistry.
2011 Oct; 286(40):34522-32. doi:
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PloS one.
2011 May; 6(5):e18894. doi:
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Advances in experimental medicine and biology.
2011; 705(?):213-28. doi:
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PloS one.
2010 Nov; 5(11):e14099. doi:
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Xenotransplantation.
2010 Nov; 17(6):440-8. doi:
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Nature biotechnology.
2010 Aug; 28(8):863-7. doi:
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Clinical and vaccine immunology : CVI.
2010 Jun; 17(6):969-78. doi:
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Tissue engineering. Part A.
2010 Apr; 16(4):1143-55. doi:
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Viruses.
2010 Apr; 2(4):1011-1049. doi:
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The Biochemical journal.
2010 Mar; 427(1):179-88. doi:
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Xenotransplantation.
2010 Jan; 17(1):48-60. doi:
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