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Basic Description
| Synonyms | 131-48-6 | N-acetyl-beta-neuraminic acid | N-acetylneuramic acid | N-Acetyl-D-neuraminic acid | Lactaminic acid | NANA | 5-N-ACETYL-BETA-D-NEURAMINIC ACID | beta-Neu5Ac | BETA-SIALIC ACID | (2S,4S,5R,6R)-5-Acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydr |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Organic oxygen compounds
- Class Organooxygen compounds
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Superclass
Organic oxygen compounds
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Sugar acids and derivatives - Sugar amino acids and derivatives - Pyranoid amino acids and derivatives - Neuraminic acids and derivatives - N-acylneuraminic acids and derivatives |
| Direct Parent | N-acylneuraminic acids |
| Alternative Parents | Neuraminic acids C-glucuronides C-glycosyl compounds Pyrans Alpha hydroxy acids and derivatives Oxanes Acetamides Secondary carboxylic acid amides Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Primary alcohols Carbonyl compounds Organonitrogen compounds Hydrocarbon derivatives Organopnictogen compounds Organic oxides |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | N-acylneuraminic acid - Neuraminic acid - C-glucuronide - C-glycosyl compound - Glycosyl compound - Alpha-hydroxy acid - Pyran - Hydroxy acid - Oxane - Acetamide - Carboxamide group - Hemiacetal - Secondary carboxylic acid amide - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Polyol - Alcohol - Hydrocarbon derivative - Organic nitrogen compound - Organopnictogen compound - Primary alcohol - Organic oxide - Carbonyl group - Organonitrogen compound - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. |
| External Descriptors | N-acetylneuraminic acid |
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Associated Targets(Human)
NEU2
Tbio
Sialidase 2 (382 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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NEU3
Tchem
Sialidase 3 (398 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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NEU4
Tchem
Sialidase 4 (267 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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NEU1
Tchem
Sialidase 1 (236 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CBX1
Tbio
Chromobox protein homolog 1 (92434 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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KPNB1
Tbio
Importin subunit beta-1/Snurportin-1 (25097 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Associated Targets(non-human)
NA
Neuraminidase (1107 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Hdac6
Histone deacetylase 6 (222 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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rep
Replicase polyprotein 1ab (378 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| IUPAC Name | (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
|---|---|
| INCHI | InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1 |
| InChIKey | SQVRNKJHWKZAKO-PFQGKNLYSA-N |
| Smiles | CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O |
| Isomeric SMILES | CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)O |
| WGK Germany | 3 |
| Molecular Weight | 309.27 |
| Beilstein | 1716283 |
| Reaxy-Rn | 2339228 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2339228&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Sensitivity | Moisture &air & heat sensitive |
|---|---|
| Specific Rotation[α] | -32 ° (C=1, H2O) |
| Melt Point(°C) | 192-194°C |
| Molecular Weight | 309.270 g/mol |
| XLogP3 | -3.500 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 5 |
| Exact Mass | 309.106 Da |
| Monoisotopic Mass | 309.106 Da |
| Topological Polar Surface Area | 177.000 Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 403.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Citations of This Product
| 1. Jiahao Hu, Yuchan You, Luwen Zhu, Jucong Zhang, Yanling Song, Jingyi Lu, Xinyi Xu, Xiaochuan Wu, Xiajie Huang, Xiaoling Xu, Yongzhong Du. (2023) Sialic Acid-Functionalized Pyroptosis Nanotuner for Epigenetic Regulation and Enhanced Cancer Immunotherapy. Small, (2306905). |
| 2. Guan Hanxiao, Xie Chen, Cao Yuqi, Huang Pingjie, Hou Dibo, Zhang Guangxin. (2023) Qualitative Identification of Sialic Acid Content Based on Terahertz Time-Domain Spectroscopy. Journal of Infrared Millimeter and Terahertz Waves, 44 (9): (780-794). |
| 3. Li Huixin, Xu Yanpeng, Wang Yang, Cui Yihao, Lin Jiake, Zhou Yuemin, Tang Shuling, Zhang Ying, Hao Haibin, Nie Zihao, Wang Xiaoyu, Tang Ruikang. (2023) Material-engineered bioartificial microorganisms enabling efficient scavenging of waterborne viruses. Nature Communications, 14 (1): (1-13). |
| 4. Shiwei Liu, Shuang Han, Yuzhuo Song, Ruonan Sun, Le Zhao, Chen Yan. (2023) Disulfide-Bridged Dendritic Organosilicas-Based Biodegradable Molecularly Imprinted Polymers for Multiple Targeting and pH/Redox-Responsive Drug Release toward Chemical/Photodynamic Synergistic Tumor Therapy. Advanced Healthcare Materials, 12 (20): (2300184). |
| 5. Liu Quanzhen, Wei Guoguang, Yang Pengfan, Wang Chengyong, Chen Kequan, Ouyang Pingkai, Zhang Alei. (2023) One-pot biosynthesis of N-acetylneuraminic acid from chitin via combination of chitin-degrading enzymes, N-acetylglucosamine-2-epimerase, and N-neuraminic acid aldolase. Frontiers in Microbiology, 14 |
| 6. Huihui Yang, Xiaosen Bai, Baolong Feng, Qinghua Wang, Li Meng, Fengzhong Wang, Yutang Wang. (2023) Application of Molecular Transformer approach for predicting the potential reactions to generate advanced glycation end products in infant formula. FOOD CHEMISTRY, 407 (135143). |
| 7. Rufeng Zhu, Yuedan Wang, Yang Tao, Yao Wang, Yuanli Chen, Mufang Li, Qiongzhen Liu, Liyan Yang, Dong Wang. (2022) Layer-by-layer assembly of composite conductive fiber-based organic electrochemical transistor for highly sensitive detection of sialic acid. ELECTROCHIMICA ACTA, 425 (140716). |
| 8. Qiang Chen, Chunjing Guo, Xiudi Zhou, Yanguo Su, Huimin Guo, Min Cao, Jing Li, Yue Zhang, Weiyi Zhao, Xin Gao, Shuqi Mi, Daquan Chen. (2022) N-acetylneuraminic acid and chondroitin sulfate modified nanomicelles with ROS-sensitive H2S donor via targeting E-selectin receptor and CD44 receptor for the efficient therapy of atherosclerosis. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 211 (259). |
| 9. Shuang Han, Yuzhuo Song, Shiwei Liu, Le Zhao, Ruonan Sun. (2022) Dual responsive molecularly imprinted polymers based on UiO-66-DOX for selective targeting tumor cells and controlled drug release. EUROPEAN POLYMER JOURNAL, 171 (111219). |
| 10. Zeng Jiaxin, Meng Yuan, Chen Shi-Yi, Zhao Gaofeng, Wang Lianchun, Zhang En-Xin, Qiu Hong. (2022) Structural characteristics of Heparan sulfate required for the binding with the virus processing Enzyme Furin. GLYCOCONJUGATE JOURNAL, 39 (3): (315-325). |
| 11. Zhang Xin, Wang Chen, Han Qing, Chen Xuan, Li Guoyun, Yu Guangli. (2021) Highly sialylated mucin-type glycopeptide from porcine intestinal mucosa after heparin extraction: O-glycan profiling and immunological activity evaluation. GLYCOCONJUGATE JOURNAL, 38 (5): (527-537). |
| 12. Xi Lin, Chunsheng Xiao, Ling Ling, Liming Guo, Xinhua Guo. (2021) A dual-mode reactive matrix for sensitive and quantitative analysis of carbohydrates by MALDI-TOF MS. TALANTA, 235 (122792). |
| 13. Junyang Chen, Shan Jiang, Mengke Wang, Xiaolei Xie, Xingguang Su. (2021) Self-assembled dual-emissive nanoprobe with metal−organic frameworks as scaffolds for enhanced ascorbic acid and ascorbate oxidase sensing. SENSORS AND ACTUATORS B-CHEMICAL, 339 (129910). |
| 14. Fan Kai, Lu Chengying, Shu Gaofeng, Lv Xiu-Ling, Qiao Enqi, Zhang Nannan, Chen Minjiang, Song Jingjing, Wu Fazong, Zhao Zhongwei, Xu Xiaoling, Xu Min, Chen Chunmiao, Yang Weibin, Sun Jihong, Du Yongzhong, Ji Jiansong. (2021) Sialic acid-engineered mesoporous polydopamine dual loaded with ferritin gene and SPIO for achieving endogenous and exogenous synergistic T2-weighted magnetic resonance imaging of HCC. JOURNAL OF NANOBIOTECHNOLOGY, 19 (1): (1-17). |
| 15. Feiyang Jin, Jing Qi, Minxia Zhu, Di Liu, Yuchan You, Gaofeng Shu, Yan Du, Jun Wang, Hui Yu, Mingchen Sun, Xiaoling Xu, Qiying Shen, Xiaoying Ying, Jiansong Ji, Yongzhong Du. (2020) NIR-Triggered Sequentially Responsive Nanocarriers Amplified Cascade Synergistic Effect of Chemo-Photodynamic Therapy with Inspired Antitumor Immunity. ACS Applied Materials & Interfaces, 12 (29): (32372–32387). |
| 16. Nian Cao, Faqiong Zhao, Baizhao Zeng. (2020) A novel ratiometric molecularly imprinted electrochemiluminescence sensor for sensitive and selective detection of sialic acid based on PEI-CdS quantum dots as anodic coreactant and cathodic luminophore. SENSORS AND ACTUATORS B-CHEMICAL, 313 (128042). |
| 17. Jinmin Wang, Limin Zhao, Bing Yan. (2020) Indicator Displacement Assay Inside Dye-Functionalized Covalent Organic Frameworks for Ultrasensitive Monitoring of Sialic Acid, an Ovarian Cancer Biomarker. ACS Applied Materials & Interfaces, 12 (11): (12990–12997). |
| 18. Xiang-Nan He, Ya-Ning Wang, Yue Wang, Zhang-Run Xu. (2020) Accurate quantitative detection of cell surface sialic acids with a background-free SERS probe. TALANTA, 209 (120579). |
| 19. Xiao-Juan Wang, Gao-Feng Shu, Xiao-Ling Xu, Chen-Han Peng, Chen-Ying Lu, Xing-Yao Cheng, Xiang-Chao Luo, Jie Li, Jing Qi, Xu-Qi Kang, Fei-Yang Jin, Min-Jiang Chen, Xiao-Ying Ying, Jian You, Yong-Zhong Du, Jian-Song Ji. (2019) Combinational protective therapy for spinal cord injury medicated by sialic acid-driven and polyethylene glycol based micelles. BIOMATERIALS, 217 (119326). |
| 20. Shaomei Xu, Songtian Che, Pinyi Ma, Fangmei Zhang, Longbin Xu, Xin Liu, Xinghua Wang, Daqian Song, Ying Sun. (2019) One-step fabrication of boronic-acid-functionalized carbon dots for the detection of sialic acid. TALANTA, 197 (548). |
| 21. Feiyang Jin, Di Liu, Hui Yu, Jing Qi, Yuchan You, Xiaoling Xu, Xuqi Kang, Xiaojuan Wang, Kongjun Lu, Xiaoying Ying, Jian You, Yongzhong Du, Jiansong Ji. (2019) Sialic Acid-Functionalized PEG–PLGA Microspheres Loading Mitochondrial-Targeting-Modified Curcumin for Acute Lung Injury Therapy. MOLECULAR PHARMACEUTICS, 16 (1): (71–85). |
| 22. Jing-Bo Hu, Di Liu, Jing Qi, Kong-jun Lu, Fei-yang Jin, Xiao-Ying Ying, Jian You, Yong-Zhong Du. (2018) An E-selectin targeting and MMP-2-responsive dextran–curcumin polymeric prodrug for targeted therapy of acute kidney injury. Biomaterials Science, 6 (12): (3397-3409). |
| 23. Lingbo Sun, Hongxia Fu, Yanru Li, Xinrui Duan, Zhengping Li. (2016) Rapid Recognition and Isolation of Live Colon Cancer Stem Cells by Using Metabolic Labeling of Azido Sugar and Magnetic Beads. ANALYTICAL CHEMISTRY, 88 (7): (3953–3958). |
| 24. Tiantian Yin, Licong Yang, Yanan Liu, Xianbo Zhou, Jing Sun, Jie Liu. (2015) Sialic acid (SA)-modified selenium nanoparticles coated with a high blood–brain barrier permeability peptide-B6 peptide for potential use in Alzheimer’s disease. Acta Biomaterialia, 25 (172). |
| 25. Qianyun Fu,Guoyun Li,Chen Wang,Ya Wang,Qinying Li,Jiejie Hao,Guangli Yu. (2019-04-10) Profiling and Structural Characterization of High Neu5Gc or Sulfate-containing O-glycans from Hyla Rabbit Intestinal Mucin.. Molecules (Basel, Switzerland), 24 ((7)): |
| 26. Xinlv Peng, Caixia Pei, Eika W. Qian, Yuguang Du, Jian-Jun Li. (2024) Co-immobilization of a bi-enzymatic cascade into hierarchically porous MIL-53 for efficient 6′-sialyllactose production. Nanoscale, |
| 27. Juncheng Liu, Xingyu Lu, Fang Fang, Kaizhang Wu, Jihong Wu, Jie Gao. (2024) Comparison of the in-vitro effect of five prebiotics with different structure on gut microbiome and metabolome. Food Bioscience, (103810). |
| 28. Sun Yunze, Mi Zhuang, Chen Xiaoyu, Li Jian-Jun, Lu Jun, Shan Xinyan, Lu Xinghua, Du Yuguang. (2024) Identification of nine mammal monosaccharides by solid-state nanopores. Scientific Reports, 14 (1): (1-9). |
| 29. Liang Shuyu, Tang Qi, Guo Xunzi, Li Zi’an, Guo Yilan, Chang Jinghan, Cheng Bo, Song Qitao, Sun Jiayu, Dai Peng, Chen Xing. (2025) Mutant glycosidases for labeling sialoglycans with high specificity and affinity. Nature Communications, 16 (1): (1-14). |
| 30. Liu Zhaohong, Xiang Peng, Zeng Shengmei, Weng Ping, Wen Yilin, Zhang Wanping, Hu Hui, Zhao Dezhang, Ma Limei, Yu Chao. (2024) N-Acetylneuraminic acid triggers endothelial pyroptosis and promotes atherosclerosis progression via GLS2-mediated glutaminolysis pathway. Cell Death Discovery, 10 (1): (1-16). |
| 31. Yuzhen Zhao, Mingge Li, Yue Guo, Jian Jin, Fei Pei, Wenya Wang, Changhua Liu, Wenyan Yu, Jinjin Shi, Na Yin. (2024) Neutrophil hitchhiking nanoparticles enhance bacteria-mediated cancer therapy via NETosis reprogramming. JOURNAL OF CONTROLLED RELEASE, 367 (661). |
| 32. Xiangyu Meng, Chen Xv, Jiaping Lv, Shuwen Zhang, Changlu Ma, Xiaoyang Pang. (2024) Optimizing Akkermansia muciniphila Isolation and Cultivation: Insights into Gut Microbiota Composition and Potential Growth Promoters in a Chinese Cohort. Microorganisms, 12 (5): (881). |
| 33. Su Fang, Jianrong Wu, Wenxuan Niu, Tiantian Zhang, Tiantian Hong, Hongtao Zhang, Xiaobei Zhan. (2024) Sialylation of dietary mucin modulate its digestibility and the gut microbiota of elderly individuals. FOOD RESEARCH INTERNATIONAL, 184 (114246). |
| 34. Zhenjun Wang, Zongtao Xie, Chuanxin Liu, Xiaojun Zhang. (2024) Synergistic chemotherapy and photothermal therapy of lung cancer using MoS2 nanosheets co-loaded with silybin and doxorubicin. Alexandria Engineering Journal, 106 (767). |
| 35. SunHongzheng , HanLongsen , GuoYueshuai , AnHuiqing , WangBing , ZhangXiangzheng , LiJiashuo , JiangYingtong , WangYue , SunGuangyi , ZhuShuai , TangShoubin , GeJuan , ChenMinjian , GuoXuejiang , WangQiang. (2024) The global phosphorylation landscape of mouse oocytes during meiotic maturation. EMBO JOURNAL, |
| 36. Zihan Zhu, Yan Zhang, Cui He, Yimin Jin, Wei Bian, Xinjing Tang, Jing Wang. (2025) Tumor microenvironment-responsive multinucleated nanocomplexes loaded with carbon dots for combined photothermal/chemodynamic therapy of breast cancer. ChemMedChem, (e202400983). |
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