Indican (BioDeep_00000006807)

   

human metabolite PANOMIX_OTCML-2023 blood metabolite Toxin natural product BioNovoGene_Lab2019


代谢物信息卡片


(2S,3R,4S,5S,6R)-2-((1H-Indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

化学式: C14H17NO6 (295.1056)
中文名称: 3-吲哚基-beta-D-吡喃葡萄糖苷, 吲哚基β-D-葡萄糖苷, 尿蓝母, 吲哚基-葡萄糖苷
谱图信息: 最多检出来源 Homo sapiens(blood) 26.82%

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CN2)OC3C(C(C(C(O3)CO)O)O)O
InChI: InChI=1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2

描述信息

Indican is a colourless, water-soluble organic compound consisting of an indole ring conjugated to glucose. It is an indole glycoside. Its hydrolysis yields β-D-glucose and indoxyl. Indoles are compounds which consist of a pyrrole ring fused to benzene to form 2,3-benzopyrrole. The oxidation of indican by a mild oxidizing agent, e.g. atmospheric oxygen or CYP450 enzymes, yields indigo dye which is blue in colour. Indican is a substance occurring naturally in the urine of humans and mammals and also in blood plasma as a normal metabolite of tryptophan. Tryptophan is first converted to indole by gut bacteria. Following absorption from the gut, indole is converted to 3-hydroxyindole (indoxyl or indican) in the liver, where it is again then conjugated with sulfuric acid or glucoronic acid through normal xenobiotic metabolism pathways. It is then transported to the kidneys for excretion. In individuals affected by the blue diaper syndrome (a rare, autosomal recessive metabolic disorder characterized in infants by bluish urine-stained diapers), the patients exhibit a defect in tryptophan metabolism, leading to an increase in indican synthesis. Indican is then excreted into the urine and from there into the diaper where, upon exposure to air, it is converted to indigo blue dye due to oxidation by atmospheric oxygen. An increased urinary excretion of indican is seen in Hartnup disease from the bacterial degradation of unabsorbed tryptophan (PMID: 19967017). Hartnup disease is an autosomal recessive metabolic disorder affecting the absorption of nonpolar amino acids (particularly tryptophan), which leads to excessive bacterial fermentation of tryptophan (to indole) in the gut. Indican has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Its excretion is decreased by the presence of Lactobacillus bacteria in the gut (PMID: 6785555 ).
Indican is an indolyl carbohydrate, a beta-D-glucoside and an exopolysaccharide.
Indican is a natural product found in Indigofera suffruticosa, Isatis tinctoria, and other organisms with data available.
Indican is a toxic metabolite derived from dietary proteins and tryptophan. In the intestine, proteins and tryptophan are converted to indole by tryptophanase-expressing organisms. In the liver, indole is hydroxylated to form indoxyl and indoxyl is sufated to produce indican. Overproduction of indican is associated with glomerular sclerosis, interstitial fibrosis and renal failure.
Indican is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. It is a colourless organic compound, soluble in water, naturally occurring in Indigofera plants. It is a precursor of indigo dye. Indican interferes with many commercial procedures for measuring total bilirubin[6] which can be a problem for renal failure patients where blood indican levels are raised. It can cause gastrointestinal symptoms in patients where protein absorption is reduced - like Hartnups disease, allowing for greater bacterial decomposition of the Tryptophan to indole and its conversion to indican.

同义名列表

44 个代谢物同义名

(2S,3R,4S,5S,6R)-2-((1H-Indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; (2S,3R,4S,5S,6R)-2-(1H-indol-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(1H-indol-3-yloxy)tetrahydropyran-3,4,5-triol; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol; (2R,3S,4S,5R)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol; 2-(hydroxymethyl)-6-(1H-indol-3-yloxy)tetrahydropyran-3,4,5- triol; Indoxyl beta-D-glucoside, Vetec(TM) reagent grade, 97\\%; Indoxyl beta-D-glucoside, BioXtra, >=97\\%; 3-(beta-D-Glucosido)indole, Plant indican; .beta.-D-Glucopyranoside, 1H-indol-3-yl; 1H-INDOL-3-YL-.BETA.-D-GLUCOPYRANOSIDE; beta-D-Glucopyranoside, 1H-indol-3-yl; Indole, 3-(beta-D-glucopyranosyloxy)-; 1H-indol-3-yl beta-D-glucopyranoside; 1H-indol-3-yl beta-glucopyranoside; 1H-indol-3-yl Β-D-glucopyranoside; 3-Indolyl-beta-D-glucopyranoside; 3-Indoxyl-beta-D-glucopyranoside; Indoxyl beta-D-glucoside, >=97\\%; 3-Indolyl-b-D-glucopyranoside; XVARCVCWNFACQC-RKQHYHRCSA-N; Indoxyl-.beta.-D-glucoside; Indoxyl beta -D-glucoside; Indoxyl-beta-D-glucoside; Indoxyl beta-D-glucoside; INDOXYLBETA-D-GLUCOSIDE; Indican (plant indican); Indoxyl |A-D-glucoside; Indoxyl-β-D-glucoside; 3-(Glucosyloxy)indole; Indican (glucoside); INDOXYL ?-GLUCOSIDE; Indican glucoside; Indican-Reaktion; indican, plant; INDICAN [MI]; SMP2_000304; Uroxanthin; Indikan; Indican; Indol-3-yl-beta-D-galactopyranoside; Indoxyl-β-D-glucoside; Indican; Indican



数据库引用编号

26 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

33 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(31)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

57 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 ALB, ANXA5, CYP2A6, DPYD, IVL, PELO
Peripheral membrane protein 4 ANXA5, AOC1, CYP1B1, GBA1
Endosome membrane 1 TF
Endoplasmic reticulum membrane 2 CYP1B1, CYP2A6
Nucleus 2 ALB, FABP2
cytosol 7 ALB, ANXA5, DPYD, FABP2, IVL, TDO2, VPS51
nuclear body 1 IVL
trans-Golgi network 1 GBA1
centrosome 2 ALB, IVL
Cell membrane 2 AOC1, SLC5A4
Multi-pass membrane protein 3 ABCC3, SLC5A1, SLC5A4
cell surface 1 TF
Golgi apparatus 3 ALB, GBA1, VPS51
Golgi membrane 1 INS
lysosomal membrane 1 GBA1
sarcolemma 1 ANXA5
Lysosome 1 GBA1
plasma membrane 5 ABCC3, AOC1, SLC5A1, SLC5A4, TF
Membrane 5 ABCC3, ANXA5, CYP1B1, CYP2A6, VPS51
apical plasma membrane 2 SLC5A1, TF
basolateral plasma membrane 1 ABCC3
extracellular exosome 7 ALB, ANXA5, AOC1, GBA1, IVL, SLC5A1, TF
Lysosome membrane 1 GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 2 ALB, GBA1
extracellular space 6 ALB, AOC1, CRP, IL6, INS, TF
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 2 SLC5A1, TF
bicellular tight junction 1 AOC1
mitochondrion 1 CYP1B1
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 3 CYP1B1, CYP2A6, VPS51
Microsome membrane 1 CYP1B1
Secreted 5 ALB, CRP, IL6, INS, TF
extracellular region 7 ALB, ANXA5, AOC1, CRP, IL6, INS, TF
basal part of cell 1 TF
Extracellular side 1 AOC1
anchoring junction 1 ALB
external side of plasma membrane 1 ANXA5
cytoplasmic vesicle 1 TF
nucleolus 1 VPS51
Early endosome 2 SLC5A1, TF
clathrin-coated pit 1 TF
recycling endosome 2 TF, VPS51
vesicle 1 TF
Apical cell membrane 1 SLC5A1
focal adhesion 1 ANXA5
Peroxisome 1 AOC1
intracellular vesicle 1 SLC5A1
collagen-containing extracellular matrix 1 ANXA5
Late endosome 1 TF
Zymogen granule membrane 1 ANXA5
ciliary basal body 1 ALB
centriole 1 ALB
Secreted, extracellular space 1 AOC1
brush border membrane 1 SLC5A1
Golgi apparatus, trans-Golgi network 1 VPS51
spindle pole 1 ALB
blood microparticle 2 ALB, TF
Basolateral cell membrane 1 ABCC3
endosome lumen 1 INS
microvillus 1 FABP2
Cornified envelope 1 IVL
basal plasma membrane 2 ABCC3, TF
trans-Golgi network membrane 1 VPS51
secretory granule lumen 2 INS, TF
HFE-transferrin receptor complex 1 TF
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 ALB, IL6, INS, TF
platelet alpha granule lumen 1 ALB
specific granule lumen 1 AOC1
endocytic vesicle 1 TF
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 TF
cytoplasmic microtubule 1 CYP2A6
Basal cell membrane 1 ABCC3
cytosolic ribosome 1 PELO
vesicle coat 1 TF
interleukin-6 receptor complex 1 IL6
apical cortex 1 FABP2
endothelial microparticle 1 ANXA5
intracellular organelle 1 SLC5A1
ciliary transition fiber 1 ALB
dense body 1 TF
EARP complex 1 VPS51
GARP complex 1 VPS51
Dom34-Hbs1 complex 1 PELO


文献列表

  • Tammy M Hsu, Ditte H Welner, Zachary N Russ, Bernardo Cervantes, Ramya L Prathuri, Paul D Adams, John E Dueber. Employing a biochemical protecting group for a sustainable indigo dyeing strategy. Nature chemical biology. 2018 03; 14(3):256-261. doi: 10.1038/nchembio.2552. [PMID: 29309053]
  • Nighat Sana, Amna Shoaib, Arshad Javaid. ANTIFUNGAL POTENTIAL OF LEAF EXTRACTS OF LEGUMINOUS TREES AGAINST SCLEROTIUM ROLFSII. African journal of traditional, complementary, and alternative medicines : AJTCAM. 2016; 13(5):54-60. doi: 10.21010/ajtcam.v13i5.8. [PMID: 28487894]
  • Minghua Chen, Lishe Gan, Sheng Lin, Xiaoliang Wang, Li Li, Yuhuan Li, Chenggen Zhu, Yanan Wang, Bingya Jiang, Jiandong Jiang, Yongchun Yang, Jiangong Shi. Alkaloids from the root of Isatis indigotica. Journal of natural products. 2012 Jun; 75(6):1167-76. doi: 10.1021/np3002833. [PMID: 22694318]
  • Heribert Warzecha, Andreas Frank, Markus Peer, Elizabeth M J Gillam, F Peter Guengerich, Matthias Unger. Formation of the indigo precursor indican in genetically engineered tobacco plants and cell cultures. Plant biotechnology journal. 2007 Jan; 5(1):185-91. doi: 10.1111/j.1467-7652.2006.00231.x. [PMID: 17207267]
  • Thierry Maugard, Estelle Enaud, Anne de la Sayette, Patrick Choisy, Marie Dominique Legoy. Beta-glucosidase-catalyzed hydrolysis of indican from leaves of Polygonum tinctorium. Biotechnology progress. 2002 Sep; 18(5):1104-8. doi: 10.1021/bp025540+. [PMID: 12363364]