3'-Sialyllactose (BioDeep_00000025570)

   

human metabolite Endogenous Toxin


代谢物信息卡片


(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

化学式: C23H39NO19 (633.2116184)
中文名称: 唾液乳糖
谱图信息: 最多检出来源 Homo sapiens(urine) 98.44%

分子结构信息

SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OC2C(C(OC(C2O)OC(C(CO)O)C(C(C=O)O)O)CO)O)O
InChI: InChI=1S/C23H39NO19/c1-7(29)24-13-8(30)2-23(22(38)39,42-19(13)15(35)10(32)4-26)43-20-16(36)12(6-28)40-21(17(20)37)41-18(11(33)5-27)14(34)9(31)3-25/h3,8-21,26-28,30-37H,2,4-6H2,1H3,(H,24,29)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19+,20-,21-,23-/m0/s1

描述信息

Sialyllactose is an oligossaccharide found in both human breast milk and cows milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin. [HMDB]
Sialyllactose is an oligossaccharide found in both human breast milk and cows milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin.

同义名列表

23 个代谢物同义名

(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate; (2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid; N-Acetylneuraminyl-2-3-galactopyranosyl-1-4-glucopyranose; alpha-Neu5ac-(2>3)-beta-delta-gal-(1>4)-delta-GLC; alpha-Neu5ac-(2>3)-beta-D-gal-(1>4)-D-GLC; 3-(N-Acetyl-alpha-neuraminosyl)lactose; 32-N-Acetyl-alpha-neuraminyllactose; a-Neu5ac-(2>3)-b-D-gal-(1>4)-D-GLC; 3-(N-Acetyl-a-neuraminosyl)lactose; 3-N-Acetylneuraminyl-delta-lactose; 32-N-Acetyl-a-neuraminyllactose; 3-N-Acetylneuraminyl-D-lactose; N-Acetylneuraminoyllactose; (2>3)-alpha-sialyllactose; 3-Sialyl-delta-lactose; (2>3)-a-sialyllactose; 3-alpha-Sialyllactose; 3-Monosialyllactose; a2,3-Sialyllactose; 3-Sialyl-D-lactose; 3-a-Sialyllactose; SCHEMBL21318923; 3-sialyllactose



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

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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

  • Denise Hoch, Waltraud Brandl, Jasmin Strutz, Harald C Köfeler, Mireille N M van Poppel, Lars Bode, Ursula Hiden, Gernot Desoye, Evelyn Jantscher-Krenn. Human Milk Oligosaccharides in Cord Blood Are Altered in Gestational Diabetes and Stimulate Feto-Placental Angiogenesis In Vitro. Nutrients. 2021 Nov; 13(12):. doi: 10.3390/nu13124257. [PMID: 34959807]
  • Seok-In Jang, Han Young Eom, Jeong Ho Hwang, Lila Kim, Jong-Hwa Lee. Simultaneous Quantification of 3'- and 6'-Sialyllactose in Rat Plasma Using Liquid Chromatography-Tandem Mass Spectrometry and Its Application to a Pharmacokinetic Study. Molecules (Basel, Switzerland). 2021 Feb; 26(4):. doi: 10.3390/molecules26041177. [PMID: 33671827]
  • Pauline Bondue, Sarah Lebrun, Bernard Taminiau, Nadia Everaert, Gisèle LaPointe, Christopher Hendrick, Juliette Gaillez, Sebastien Crèvecoeur, Georges Daube, Véronique Delcenserie. Effect of Bifidobacterium crudilactis and 3'-sialyllactose on the toddler microbiota using the SHIME® model. Food research international (Ottawa, Ont.). 2020 12; 138(Pt A):109755. doi: 10.1016/j.foodres.2020.109755. [PMID: 33292938]
  • Zhongkui Li, Zhijian Ni, Xiangsong Chen, Gang Wang, Jinyong Wu, Jianming Yao. Multi-Enzymatic Cascade One-Pot Biosynthesis of 3'-Sialyllactose Using Engineered Escherichia coli. Molecules (Basel, Switzerland). 2020 Aug; 25(16):. doi: 10.3390/molecules25163567. [PMID: 32781536]
  • Sun-Hyung Ha, Choong-Hwan Kwak, Jun-Young Park, Fukushi Abekura, Young-Choon Lee, Jong-Suk Kim, Tae-Wook Chung, Cheorl-Ho Kim. 3'-sialyllactose targets cell surface protein, SIGLEC-3, and induces megakaryocyte differentiation and apoptosis by lipid raft-dependent endocytosis. Glycoconjugate journal. 2020 04; 37(2):187-200. doi: 10.1007/s10719-019-09902-1. [PMID: 31900723]
  • Sira Carolin Günther, Julian David Maier, Janine Vetter, Nikita Podvalnyy, Nikolay Khanzhin, Thierry Hennet, Silke Stertz. Antiviral potential of 3'-sialyllactose- and 6'-sialyllactose-conjugated dendritic polymers against human and avian influenza viruses. Scientific reports. 2020 01; 10(1):768. doi: 10.1038/s41598-020-57608-4. [PMID: 31964943]
  • Keita Yamada, Kiyoshi Higashi, Hirohisa Nagahori, Koichi Saito. Circulating natural antibodies against 3'-sialyllactose complement the diagnostic performance of CA19-9 for the early detection of pancreatic ductal adenocarcinoma. Cancer biomarkers : section A of Disease markers. 2020; 27(1):121-128. doi: 10.3233/cbm-190158. [PMID: 31771041]
  • Ramesh Prasad Pandey, Dae Hee Kim, Jinsuk Woo, Jaeyoung Song, Sang Ho Jang, Joon Bae Kim, Kwang Myun Cheong, Jin Sik Oh, Jae Kyung Sohng. Broad-spectrum neutralization of avian influenza viruses by sialylated human milk oligosaccharides: in vivo assessment of 3'-sialyllactose against H9N2 in chickens. Scientific reports. 2018 02; 8(1):2563. doi: 10.1038/s41598-018-20955-4. [PMID: 29416087]
  • Masanori Nagao, Yurina Fujiwara, Teruhiko Matsubara, Yu Hoshino, Toshinori Sato, Yoshiko Miura. Design of Glycopolymers Carrying Sialyl Oligosaccharides for Controlling the Interaction with the Influenza Virus. Biomacromolecules. 2017 Dec; 18(12):4385-4392. doi: 10.1021/acs.biomac.7b01426. [PMID: 29111681]
  • Vera Bunesova, Christophe Lacroix, Clarissa Schwab. Fucosyllactose and L-fucose utilization of infant Bifidobacterium longum and Bifidobacterium kashiwanohense. BMC microbiology. 2016 10; 16(1):248. doi: 10.1186/s12866-016-0867-4. [PMID: 27782805]
  • Zhongjie Li, Yiran Zhao, Weiwei Lin, Min Ye, Xiaomei Ling. Rapid screening and identification of active ingredients in licorice extract interacting with V3 loop region of HIV-1 gp120 using ACE and CE-MS. Journal of pharmaceutical and biomedical analysis. 2015; 111(?):28-35. doi: 10.1016/j.jpba.2015.02.021. [PMID: 25854854]
  • Lars Bode, Louise Kuhn, Hae-Young Kim, Lauren Hsiao, Caroline Nissan, Moses Sinkala, Chipepo Kankasa, Mwiya Mwiya, Donald M Thea, Grace M Aldrovandi. Human milk oligosaccharide concentration and risk of postnatal transmission of HIV through breastfeeding. The American journal of clinical nutrition. 2012 Oct; 96(4):831-9. doi: 10.3945/ajcn.112.039503. [PMID: 22894939]
  • Stéphane Woerly, Sébastien Fort, Isabelle Pignot-Paintrand, Cécile Cottet, Carole Carcenac, Marc Savasta. Development of a sialic acid-containing hydrogel of poly[N-(2-hydroxypropyl) methacrylamide]: characterization and implantation study. Biomacromolecules. 2008 Sep; 9(9):2329-37. doi: 10.1021/bm800234r. [PMID: 18715030]
  • Susanne M C Johansson, Niklas Arnberg, Mikael Elofsson, Göran Wadell, Jan Kihlberg. Multivalent HSA conjugates of 3'-sialyllactose are potent inhibitors of adenoviral cell attachment and infection. Chembiochem : a European journal of chemical biology. 2005 Feb; 6(2):358-64. doi: 10.1002/cbic.200400227. [PMID: 15678425]
  • Waldemar Popik, Timothy M Alce. CD4 receptor localized to non-raft membrane microdomains supports HIV-1 entry. Identification of a novel raft localization marker in CD4. The Journal of biological chemistry. 2004 Jan; 279(1):704-12. doi: 10.1074/jbc.m306380200. [PMID: 14570906]