N,N'-diacetylchitobiose (BioDeep_00000004734)

Main id: BioDeep_00000838653

 

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


N-[(3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

化学式: C16H28N2O11 (424.1693)
中文名称: N,N-二乙酰基壳二糖
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)NC1C(C(C(OC1O)CO)OC2C(C(C(C(O2)CO)O)O)NC(=O)C)O
InChI: InChI=1S/C16H28N2O11/c1-5(21)17-9-13(25)14(8(4-20)27-15(9)26)29-16-10(18-6(2)22)12(24)11(23)7(3-19)28-16/h7-16,19-20,23-26H,3-4H2,1-2H3,(H,17,21)(H,18,22)

描述信息

N,N-diacetylchitobiose, also known as (GlcNAc)2, is classified as a member of the Acylaminosugars. Acylaminosugars are organic compounds containing a sugar linked to a chain through N-acyl group. N,N-diacetylchitobiose is considered to be soluble (in water) and acidic. N,N-diacetylchitobiose may be a unique E.coli metabolite
N,N'-Diacetylchitobiose is a dimer of β(1,4) linked N-acetyl-D glucosamine. N,N'-Diacetylchitobiose is the hydrolysate of chitin and can be used as alternative carbon source by?E. coli[1].

同义名列表

12 个代谢物同义名

N-[(3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; 2-Acetamido-2-deoxy-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-D-glucopyranose; 4-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-D-glucose; N,N-diacetylchitobioside; Bis(N-acetyl)chitobiose; N,N-Diacetylchitobiose; Di-N-acetylchitobiose; Diacetylchitobiose; Chitobiose; (GlcNAc)2; N,N'-Diacetylchitobiose; Chitobiose



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(5)

PlantCyc(0)

代谢反应

20 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(14)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(5)

COVID-19 Disease Map(0)

PathBank(1)

  • Chitobiose Degradation: Diacetylchitobiose-6-phosphate + Water ⟶ Acetic acid + N'-monoacetylchitobiose-6'-phosphate

PharmGKB(0)

6 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。

亚细胞结构定位 关联基因列表
Cytoplasm 6 ABCB1, CHIA, GNPDA1, NGLY1, PFDN5, PLA2G12A
Peripheral membrane protein 1 GBA1
Endosome membrane 1 TF
Endoplasmic reticulum membrane 3 HSP90B1, MOGS, P4HTM
Nucleus 3 HSP90B1, NGLY1, PFDN5
cytosol 5 ENGASE, GNPDA1, HSP90B1, NGLY1, PFDN5
trans-Golgi network 1 GBA1
nucleoplasm 1 MAN2B1
Cell membrane 2 ABCB1, TNF
Multi-pass membrane protein 1 ABCB1
cell surface 4 ABCB1, TF, TNF, UMOD
Golgi apparatus 1 GBA1
lysosomal membrane 2 GAA, GBA1
neuronal cell body 1 TNF
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 ENGASE
Lysosome 6 CHIT1, CTBS, GAA, GBA1, MAN2B1, MANBA
plasma membrane 5 ABCB1, GAA, MANBA, TF, TNF
Membrane 6 ABCB1, GAA, HSP90B1, MOGS, P4HTM, UMOD
apical plasma membrane 3 ABCB1, TF, UMOD
basolateral plasma membrane 1 UMOD
extracellular exosome 9 ABCB1, GAA, GBA1, GNPDA1, HSP90B1, MAN2B1, MOGS, TF, UMOD
Lysosome membrane 2 GAA, GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 5 GBA1, HSP90B1, MOGS, P4HTM, UMOD
extracellular space 8 CHIA, CHIT1, CTBS, IL2, MAN2B1, TF, TNF, UMOD
lysosomal lumen 4 GAA, GBA1, MAN2B1, MANBA
perinuclear region of cytoplasm 2 HSP90B1, TF
protein-containing complex 1 HSP90B1
intracellular membrane-bounded organelle 2 GAA, MAN2B1
Secreted 5 GAA, IL2, PLA2G12A, TF, UMOD
extracellular region 9 CHIA, CHIT1, GAA, HSP90B1, IL2, MAN2B1, PLA2G12A, TF, TNF
basal part of cell 1 TF
ciliary membrane 1 UMOD
external side of plasma membrane 1 TNF
cytoplasmic vesicle 1 TF
midbody 1 HSP90B1
Early endosome 1 TF
clathrin-coated pit 1 TF
recycling endosome 2 TF, TNF
Single-pass type II membrane protein 3 MOGS, P4HTM, TNF
vesicle 1 TF
Apical cell membrane 2 ABCB1, UMOD
Membrane raft 1 TNF
focal adhesion 1 HSP90B1
collagen-containing extracellular matrix 1 HSP90B1
Late endosome 1 TF
cilium 1 UMOD
phagocytic cup 1 TNF
spindle pole 1 UMOD
blood microparticle 1 TF
Basolateral cell membrane 1 UMOD
Lipid-anchor, GPI-anchor 1 UMOD
tertiary granule membrane 1 GAA
Melanosome 1 HSP90B1
side of membrane 1 UMOD
sperm plasma membrane 1 HSP90B1
intermediate filament cytoskeleton 1 PFDN5
basal plasma membrane 1 TF
secretory granule lumen 1 TF
HFE-transferrin receptor complex 1 TF
Golgi lumen 1 UMOD
endoplasmic reticulum lumen 2 HSP90B1, TF
specific granule lumen 1 CHIT1
tertiary granule lumen 1 CHIT1
extrinsic component of membrane 1 UMOD
endocytic vesicle 1 TF
azurophil granule membrane 2 GAA, MANBA
azurophil granule lumen 1 MAN2B1
clathrin-coated endocytic vesicle membrane 1 TF
Sarcoplasmic reticulum lumen 1 HSP90B1
prefoldin complex 1 PFDN5
ficolin-1-rich granule membrane 1 GAA
external side of apical plasma membrane 1 ABCB1
Cell projection, cilium membrane 1 UMOD
vesicle coat 1 TF
endocytic vesicle lumen 1 HSP90B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
endoplasmic reticulum chaperone complex 1 HSP90B1
[Uromodulin, secreted form]: Secreted 1 UMOD
autolysosome lumen 1 GAA
dense body 1 TF
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Saumashish Mukherjee, Prashanta Kumar Behera, Jogi Madhuprakash. Efficient conversion of crystalline chitin to N-acetylglucosamine and N,N'-diacetylchitobiose by the enzyme cocktail produced by Paenibacillus sp. LS1. Carbohydrate polymers. 2020 Dec; 250(?):116889. doi: 10.1016/j.carbpol.2020.116889. [PMID: 33049827]
  • Fangmeng Chu, Di Wang, Tian Liu, Hongyu Han, Yike Yu, Qing Yang. An optimized cocktail of chitinolytic enzymes to produce N,N'-diacetylchitobiose and N-acetyl-d-glucosamine from defatted krill by-products. International journal of biological macromolecules. 2019 Jul; 133(?):1029-1034. doi: 10.1016/j.ijbiomac.2019.04.114. [PMID: 31004644]
  • Peng Han, Chengcheng Yang, Xiaobo Liang, Lirong Li. Identification and characterization of a novel chitinase with antifungal activity from 'Baozhu' pear (Pyrus ussuriensis Maxim.). Food chemistry. 2016 Apr; 196(?):808-14. doi: 10.1016/j.foodchem.2015.10.006. [PMID: 26593558]
  • Chaitanya A K Koppisetty, Martin Frank, Alexander P Lyubartsev, Per-Georg Nyholm. Binding energy calculations for hevein-carbohydrate interactions using expanded ensemble molecular dynamics simulations. Journal of computer-aided molecular design. 2015 Jan; 29(1):13-21. doi: 10.1007/s10822-014-9792-5. [PMID: 25432318]
  • Helena Ryšlavá, Robert Valenta, Veronika Hýsková, Tomáš Křížek, Jiří Liberda, Pavel Coufal. Purification and enzymatic characterization of tobacco leaf β-N-acetylhexosaminidase. Biochimie. 2014 Dec; 107 Pt B(?):263-9. doi: 10.1016/j.biochi.2014.09.006. [PMID: 25242193]
  • Simone Vincenzi, Jan Bierma, Samanthi I Wickramasekara, Andrea Curioni, Diana Gazzola, Alan T Bakalinsky. Characterization of a grape class IV chitinase. Journal of agricultural and food chemistry. 2014 Jun; 62(24):5660-8. doi: 10.1021/jf501225g. [PMID: 24845689]
  • Ryuichi Masaka, Makoto Ogata, Yoshinori Misawa, Megumi Yano, Chika Hashimoto, Takeomi Murata, Hirokazu Kawagishi, Taichi Usui. Molecular design of N-linked tetravalent glycosides bearing N-acetylglucosamine, N,N'-diacetylchitobiose and N-acetyllactosamine: Analysis of cross-linking activities with WGA and ECA lectins. Bioorganic & medicinal chemistry. 2010 Jan; 18(2):621-9. doi: 10.1016/j.bmc.2009.12.006. [PMID: 20056550]
  • Andreas Marquardt, Bogdan Bernevic, Michael Przybylski. Identification, affinity characterisation and biological interactions of lectin-like peptide-carbohydrate complexes derived from human TNF-alpha using high-resolution mass spectrometry. Journal of peptide science : an official publication of the European Peptide Society. 2007 Dec; 13(12):803-10. doi: 10.1002/psc.902. [PMID: 17918767]
  • X Xiao, F Wang, A Saito, J Majka, A Schlösser, H Schrempf. The novel Streptomyces olivaceoviridis ABC transporter Ngc mediates uptake of N-acetylglucosamine and N,N'-diacetylchitobiose. Molecular genetics and genomics : MGG. 2002 Jun; 267(4):429-39. doi: 10.1007/s00438-002-0640-2. [PMID: 12111550]
  • H C Siebert, S André, J L Asensio, F J Cañada, X Dong, J F Espinosa, M Frank, M Gilleron, H Kaltner, T Kozár, N V Bovin, C W von Der Lieth, J F Vliegenthart, J Jiménez-Barbero, H J Gabius. A new combined computational and NMR-spectroscopical strategy for the identification of additional conformational constraints of the bound ligand in an aprotic solvent. Chembiochem : a European journal of chemical biology. 2000 Oct; 1(3):181-95. doi: 10.1002/1439-7633(20001002)1:3<181::aid-cbic181>3.0.co;2-9. [PMID: 11828411]
  • B Coddeville, E Regoeczi, G Strecker, Y Plancke, G Spik. Structural analysis of trisialylated biantennary glycans isolated from mouse serum transferrin. Characterization of the sequence Neu5Gc(alpha 2-3)Gal(beta 1-3)[Neu5Gc(alpha 2-6)]GlcNAc(beta 1-2)Man. Biochimica et biophysica acta. 2000 Jul; 1475(3):321-8. doi: 10.1016/s0304-4165(00)00083-0. [PMID: 10913832]
  • Y Konami, K Yamamoto, T Osawa, T Irimura. Correlation between carbohydrate-binding specificity and amino acid sequence of carbohydrate-binding regions of Cytisus-type anti-H(O) lectins. FEBS letters. 1992 Jun; 304(2-3):129-35. doi: 10.1016/0014-5793(92)80603-e. [PMID: 1618311]
  • R Krishnamoorthi, S Nemmers, B Tobias. Natural abundance 15N NMR assignments delineate structural differences between intact and reactive-site hydrolyzed Cucurbita maxima trypsin inhibitor III. FEBS letters. 1992 Jun; 304(2-3):149-52. doi: 10.1016/0014-5793(92)80607-i. [PMID: 1618315]
  • S Auricchio, G De Ritis, M De Vincenzi, G Magazzù, L Maiuri, E Mancini, M Minetti, O Sapora, V Silano. Mannan and oligomers of N-acetylglucosamine protect intestinal mucosa of celiac patients with active disease from in vitro toxicity of gliadin peptides. Gastroenterology. 1990 Oct; 99(4):973-8. doi: 10.1016/0016-5085(90)90615-8. [PMID: 2394351]
  • J van Pelt, K Hård, J P Kamerling, J F Vliegenthart, A J Reuser, H Galjaard. Isolation and structural characterization of twenty-one sialyloligosaccharides from galactosialidosis urine. An intact N,N'-diacetylchitobiose unit at the reducing end of a diantennary structure. Biological chemistry Hoppe-Seyler. 1989 Mar; 370(3):191-203. doi: 10.1515/bchm3.1989.370.1.191. [PMID: 2713102]
  • E W Watt, J Wiley, G F Fletcher. Effect of dietary control and exercise training on daily food intake and serum lipids in postmyocardial infarction patients. The American journal of clinical nutrition. 1976 Aug; 29(8):900-4. doi: 10.1093/ajcn/29.8.900. [PMID: 181978]