Indoxyl (BioDeep_00000005906)

 

Secondary id: BioDeep_00000405581

human metabolite Endogenous natural product


代谢物信息卡片


1H-Indol-3-ol

化学式: C8H7NO (133.0528)
中文名称: 3-羟基吲哚
谱图信息: 最多检出来源 Viridiplantae(plant) 23.09%

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CN2)O
InChI: InChI=1S/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H

描述信息

Indoxyl, also known as 1H-indol-3-ol, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Indoxyl is isomeric with oxindol and is obtained as an oily liquid. Indoxyl exists in all living organisms, ranging from bacteria to humans. Indoxyl is obtained from indican, which is a glycoside. Obermayers reagent is a dilute solution FeCl3 in hydrochloric acid. The hydrolysis of indican yields β-D-glucose and indoxyl. Indigo dye is a product of the reaction of indoxyl by a mild oxidizing agent such as atmospheric oxygen. In chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO. Indoxyl can be found in urine and is titrated with Obermayers reagent.
Indigo dye is a product of the reaction of indoxyl by a mild oxidizing agent, eg. atmospheric oxygen.

同义名列表

3 个代谢物同义名

1H-Indol-3-ol; indoxyl; Indoxyl



数据库引用编号

19 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

64 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(62)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

20 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 8 AHR, CYP2A6, CYP2B6, CYP2E1, G6PD, SULT1A1, SYK, XDH
Golgi apparatus, trans-Golgi network membrane 1 LRBA
Peripheral membrane protein 4 CYP1B1, CYP2B6, CYP2E1, G6PD
Endoplasmic reticulum membrane 6 CYP1A2, CYP1B1, CYP2A6, CYP2B6, CYP2E1, LRBA
Nucleus 2 AHR, SYK
cytosol 8 AHR, G6PD, LIPE, LRBA, SULT1A1, SYK, TDO2, XDH
nucleoplasm 1 AHR
Cell membrane 6 FNDC5, LIPE, LRBA, MGAM, SYK, TNF
cell surface 1 TNF
Golgi apparatus 1 LRBA
lysosomal membrane 1 LRBA
mitochondrial inner membrane 1 CYP2E1
neuronal cell body 1 TNF
Cytoplasm, cytosol 3 G6PD, LIPE, SYK
plasma membrane 6 FNDC5, LCT, LRBA, MGAM, SYK, TNF
Membrane 7 CYP1B1, CYP2A6, FNDC5, G6PD, LIPE, LRBA, MGAM
apical plasma membrane 1 MGAM
caveola 1 LIPE
extracellular exosome 2 G6PD, MGAM
Lysosome membrane 1 LRBA
endoplasmic reticulum 1 FNDC5
extracellular space 4 COL2A1, IL4, TNF, XDH
mitochondrion 1 CYP1B1
protein-containing complex 2 AHR, SYK
intracellular membrane-bounded organelle 6 CYP1A2, CYP1B1, CYP2A6, CYP2B6, CYP2E1, G6PD
Microsome membrane 4 CYP1A2, CYP1B1, CYP2B6, CYP2E1
Single-pass type I membrane protein 2 FNDC5, LCT
Secreted 4 COL2A1, FNDC5, IL4, MGAM
extracellular region 6 COL2A1, FNDC5, IL4, MGAM, PLA2G7, TNF
cytoplasmic side of plasma membrane 1 G6PD
Single-pass membrane protein 2 LRBA, MGAM
transcription regulator complex 1 AHR
centriolar satellite 1 G6PD
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 COL2A1
high-density lipoprotein particle 1 PLA2G7
low-density lipoprotein particle 1 PLA2G7
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 LCT
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 1 TNF
Peroxisome 1 XDH
basement membrane 1 COL2A1
collagen trimer 1 COL2A1
sarcoplasmic reticulum 1 XDH
peroxisomal membrane 1 FNDC5
collagen-containing extracellular matrix 1 COL2A1
chromatin 1 AHR
phagocytic cup 1 TNF
Secreted, extracellular space 1 PLA2G7
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
aryl hydrocarbon receptor complex 1 AHR
tertiary granule membrane 1 MGAM
Peroxisome membrane 1 FNDC5
endoplasmic reticulum lumen 1 COL2A1
cytoplasmic microtubule 1 CYP2A6
ficolin-1-rich granule membrane 1 MGAM
external side of apical plasma membrane 1 LCT
early phagosome 1 SYK
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 SYK
collagen type II trimer 1 COL2A1
collagen type XI trimer 1 COL2A1
B cell receptor complex 1 SYK
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Teresa Arcidiacono, Lorenza Macrina, Simone Premaschi, Arianna Bologna, Giulia Magni, Nadia Foligno, Monica Avino, Cristina Belloni, Nicola Palmieri, Ferruccio Conte, Sergio Bisegna, Marco Simonini, Giorgio Slaviero, Massimo Locatelli, Giuseppe Vezzoli. Serum concentrations of free indoxyl and p-cresyl sulfate are associated with mineral metabolism variables and cardiovascular risk in hemodialysis patients. Journal of nephrology. 2022 06; 35(5):1457-1465. doi: 10.1007/s40620-022-01271-7. [PMID: 35175580]
  • Lara Caldiroli, Silvia Armelloni, Alessandra Eskander, Piergiorgio Messa, Vittoria Rizzo, Elisabetta Margiotta, Matteo Cesari, Simone Vettoretti. Association between the uremic toxins indoxyl-sulfate and p-cresyl-sulfate with sarcopenia and malnutrition in elderly patients with advanced chronic kidney disease. Experimental gerontology. 2021 05; 147(?):111266. doi: 10.1016/j.exger.2021.111266. [PMID: 33529747]
  • Shuhei Tsutsumi, Yuki Tokunaga, Shunsuke Shimizu, Hideki Kinoshita, Masateru Ono, Katsuhisa Kurogi, Yoichi Sakakibara, Masahito Suiko, Ming-Cheh Liu, Shin Yasuda. Effects of indole and indoxyl on the intracellular oxidation level and phagocytic activity of differentiated HL-60 human macrophage cells. The Journal of toxicological sciences. 2020; 45(9):569-579. doi: 10.2131/jts.45.569. [PMID: 32879256]
  • 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]
  • Vishal D Shah, Betsy J Walton, Amanda G Culp, Stephen Castellino. Investigation of Blue Bedding in Cages Housing Treatment-Naïve Hamsters. Journal of the American Association for Laboratory Animal Science : JAALAS. 2015 Nov; 54(6):799-802. doi: NULL. [PMID: 26632791]
  • Guang-Huey Lin, Hao-Ping Chen, Jui-Hsin Huang, Tze-Tze Liu, Tze-Kang Lin, Shih-Jon Wang, Cheng-Hsing Tseng, Hung-Yu Shu. Identification and characterization of an indigo-producing oxygenase involved in indole 3-acetic acid utilization by Acinetobacter baumannii. Antonie van Leeuwenhoek. 2012 May; 101(4):881-90. doi: 10.1007/s10482-012-9704-4. [PMID: 22311185]
  • Dottie R Brundige, Elizabeth A Maga, Kirk C Klasing, James D Murray. Consumption of pasteurized human lysozyme transgenic goats' milk alters serum metabolite profile in young pigs. Transgenic research. 2010 Aug; 19(4):563-74. doi: 10.1007/s11248-009-9334-4. [PMID: 19847666]
  • David M Mutch, Jens C Fuhrmann, Dietrich Rein, Jan C Wiemer, Jean-Luc Bouillot, Christine Poitou, Karine Clément. Metabolite profiling identifies candidate markers reflecting the clinical adaptations associated with Roux-en-Y gastric bypass surgery. PloS one. 2009 Nov; 4(11):e7905. doi: 10.1371/journal.pone.0007905. [PMID: 19936240]
  • Carlos L Céspedes, Julio Alarcon, Maribel Valdez-Morales, Octavio Paredes-López. Antioxidant activity of an unusual 3-hydroxyindole derivative isolated from fruits of Aristotelia chilensis (Molina) Stuntz. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 Sep; 64(9-10):759-62. doi: 10.1515/znc-2009-9-1024. [PMID: 19957448]
  • 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]
  • E M Gillam, L M Notley, H Cai, J J De Voss, F P Guengerich. Oxidation of indole by cytochrome P450 enzymes. Biochemistry. 2000 Nov; 39(45):13817-24. doi: 10.1021/bi001229u. [PMID: 11076521]
  • T Sakai, A Takadate, M Otagiri. Characterization of binding site of uremic toxins on human serum albumin. Biological & pharmaceutical bulletin. 1995 Dec; 18(12):1755-61. doi: 10.1248/bpb.18.1755. [PMID: 8787801]
  • R Gossrau. Indoxyl alfa-D-galactoside as the temporarily last substrate for glycosidase histochemistry. The present state of the art in histochemical glycosidase research using indoxyl glycosidas. Folia histochemica et cytobiologica. 1990; 28(3):129-43. doi: . [PMID: 2096081]
  • N H Heegaard. Visualization of alkaline phosphatase-labelled antibodies on immunoblots by means of formazan staining using indoxyl phosphate and thiazolyl blue. Applied and theoretical electrophoresis : the official journal of the International Electrophoresis Society. 1990; 1(5):261-4. doi: NULL. [PMID: 1711901]
  • P Sinha. Detection of alkaline phosphatase activity after conventional isoelectric focusing by an indoxyl-tetrazolium salt technique. Journal of biochemical and biophysical methods. 1985 Nov; 11(6):327-40. doi: 10.1016/0165-022x(85)90025-9. [PMID: 2415567]
  • J W Faigle, H Stierlin, H Mory, T Winkler, H P Kriemler. Indoxyl derivatives of drug metabolites. Experientia. 1985 Apr; 41(4):476-8. doi: 10.1007/bf01966155. [PMID: 2859218]
  • S Kirkeby, D Moe, E Salling. Kinetics of the oxidation of indoxyl liberated from indoxyl phosphate by kidney alkaline phosphatase. Basic and applied histochemistry. 1982; 26(2):71-8. doi: NULL. [PMID: 7115263]
  • A BIASOTTI, C GUERRA. [Blood indoxyl. Its clinical value in diseases of the kidney]. La Semana medica. 1960 Jan; 116(?):85-95. doi: NULL. [PMID: 13800446]
  • I SANO, P DECKER. [Cold-induced Millon reaction and indoxyl sulfuric acid as the same chromogen]. Klinische Wochenschrift. 1955 Jul; 33(25-26):614-6. doi: 10.1007/bf01472792. [PMID: 13243613]
  • P DECKER, I SANO. [Identification of indoxyl sulfuric acid as chromogen of the Millon reaction with urine in cold]. Hoppe-Seyler's Zeitschrift fur physiologische Chemie. 1955 Jun; 300(5-6):252-60. doi: NULL. [PMID: 13294811]
  • D SPISNI, V CAPPA. [Relation of nutrition to urinary indoxyl compounds in cattle]. Bollettino della Societa italiana di biologia sperimentale. 1954 Dec; 30(12):1417-8. doi: NULL. [PMID: 14389579]