Iduronic acid (BioDeep_00000014472)
Secondary id: BioDeep_00001870529
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C6H10O7 (194.042651)
中文名称: L-艾杜糖醛酸
谱图信息:
最多检出来源 Homo sapiens(blood) 18.18%
分子结构信息
SMILES: C(=O)C(C(C(C(C(=O)O)O)O)O)O
InChI: InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4-,5+/m1/s1
描述信息
Iduronic acid is a constituent of glycosaminoglycans heparin and heparan sulfate in varying proportions providing considerable diversity in sequence and biological function. The glycosaminoglycans (GAGs) are linear polysaccharides with alternating uronic acids (Iduronic acid and Glucuronic acid) and hexosamine residues, in which a limited set of monosaccharide units gives rise to a number of complex sequences by variable substitution with O-sulfate, N-sulfate, and N-acetyl groups. GAGs usually exist as the O-linked side-chains of proteoglycans, displaying a set of physiological functions which is remarkably wide and as yet incompletely explored. They may act as structural components of connective tissue and the extracellular matrix, or as specific ligands in the relationship between the cell surface and its surroundings. Heparan sulfate exists on the surface of most or all mammalian cells and can display a remarkable range of different sequence motifs; its range of interactions and possible functions reflect its structural complexity. The main repeat unit of heparin structurally resembles the protein binding sequences in heparan sulfate, but contains a higher percentage of sulfated residues. Utilized therapeutically as an anticoagulant and readily available in good quantities heparin serves as a useful model for heparan sulfate. Theoretical and experimental studies indicate that L-Iduronic acid residues of glycosaminoglycans are in equilibrium of different conformations, the relative proportion of conformers being a function of sulfation pattern and sequence. This unique conformational flexibility may provide an explanation for the stronger binding and associated higher biological activities of Iduronic acid-containing glycosaminoglycans (such as heparin, heparan sulfate and dermatan sulfate) as compared with other GAGs having similar charge density but with the more rigid glucuronic acid as the major uronic acid residue. Dermatan sulfates and heparins, which contain L-Iduronic acid in their backbone, show higher low-density lipoprotein (LDL)-affinity than chondroitin sulfates, which contain only D-glucuronic acid. Though confirming a non-specific, predominantly electrostatic interaction between GAGs and LDL, these results indicate modulation of LDL affinity by the polysaccharide backbone. Naturally oversulfated dermatan sulfate (SO3H/COOH ca. 1.2), mainly oversulfated at C-2 of Iduronic acid residues, show comparatively higher anticoagulant activity. (PMID: 3076283, 8466951, 8542607, 11087707).
Iduronic acid is a constituent of glycosaminoglycans heparin and heparan sulfate in varying proportions providing considerable diversity in sequence and biological function.
同义名列表
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:85187
- ChEBI: CHEBI:47903
- ChEBI: CHEBI:47902
- KEGG: C06472
- PubChem: 441039
- PubChem: 18845
- HMDB: HMDB0002704
- Metlin: METLIN63648
- Wikipedia: Iduronic acid
- MeSH: Iduronic Acid
- foodb: FDB023047
- chemspider: 17794
- CAS: 21675-53-6
- CAS: 3402-98-0
- CAS: 2073-35-0
- CAS: 2240-07-5
- PubChem: 8704
- PDB-CCD: IDR
- 3DMET: B05205
- NIKKAJI: J1.047.082J
- RefMet: Iduronic acid
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
- Lorenzo Badenetti, Rosa Manzoli, Marta Trevisan, Francesca D'Avanzo, Rosella Tomanin, Enrico Moro. A novel CRISPR/Cas9-based iduronate-2-sulfatase (IDS) knockout human neuronal cell line reveals earliest pathological changes.
Scientific reports.
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Carbohydrate polymers.
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Glycobiology.
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The Journal of biological chemistry.
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Biomacromolecules.
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The Journal of biological chemistry.
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The Journal of biological chemistry.
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The Journal of biological chemistry.
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Biochemistry.
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European journal of oral sciences.
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The Journal of biological chemistry.
1997 Sep; 272(37):23172-9. doi:
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The Biochemical journal.
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Experimental cell research.
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Biopolymers.
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Journal of biochemistry.
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The Biochemical journal.
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