Indole (BioDeep_00000002913)

 

Secondary id: BioDeep_00000400203, BioDeep_00000860852

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


代谢物信息卡片


2,3-Benzopyrrole

化学式: C8H7N (117.0578)
中文名称: 吲哚
谱图信息: 最多检出来源 Homo sapiens(plant) 8.89%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Indole. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/indole (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002913). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1(C=CC=C2)=C2NC=C1
InChI: InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

描述信息

Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. Indole is a microbial metabolite and it can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, indole has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. As a volatile organic compound, indole has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230). Natural jasmine oil, used in the perfume industry, contains around 2.5\\\\\% of indole. Indole also occurs in coal tar. Indole has been found to be produced in a number of bacterial genera including Alcaligenes, Aspergillus, Escherichia, and Pseudomonas (PMID: 23194589, 2310183, 9680309). Indole plays a role in bacterial biofilm formation, bacterial motility, bacterial virulence, plasmid stability, and antibiotic resistance. It also functions as an intercellular signalling molecule (PMID: 26115989). Recently, it was determined that the bacterial membrane-bound histidine sensor kinase (HK) known as CpxA acts as a bacterial indole sensor to facilitate signalling (PMID: 31164470). It has been found that decreased indole concentrations in the gut promote bacterial pathogenesis, while increased levels of indole in the gut decrease bacterial virulence gene expression (PMID: 31164470). As a result, enteric pathogens sense a gradient of indole concentrations in the gut to migrate to different niches and successfully establish an infection.
Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs

Indole. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=120-72-9 (retrieved 2024-07-16) (CAS RN: 120-72-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Indole is an endogenous metabolite.
Indole is an endogenous metabolite.

同义名列表

11 个代谢物同义名

2,3-Benzopyrrole; Benzo[b]pyrrole; 1-Benzazole; 1-Azaindene; 1H-indole; Ketole; Indole; indol; Indole; Indole; Indole



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(6)

PlantCyc(2)

代谢反应

775 个相关的代谢反应过程信息。

Reactome(65)

BioCyc(98)

WikiPathways(0)

Plant Reactome(330)

INOH(0)

PlantCyc(278)

COVID-19 Disease Map(0)

PathBank(4)

PharmGKB(0)

178 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 14 AHR, AKT1, ALB, ALOX5, CAT, CNR1, CNR2, IDO1, MT1L, ODC1, PPARG, PTGS1, TNK1, TUBB4B
Peripheral membrane protein 3 ALOX5, PTGS1, TNK1
Endoplasmic reticulum membrane 1 PTGS1
Nucleus 7 AHR, AKT1, ALB, MT1L, NR1I2, PPARG, TUBB4B
cytosol 9 AHR, AKT1, ALB, ALOX5, CAT, IDO1, ODC1, PPARG, TUBB4B
dendrite 2 CNR2, HTR2A
nuclear body 1 NR1I2
centrosome 1 ALB
nucleoplasm 5 AHR, AKT1, ALOX5, NR1I2, PPARG
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 3 AKT1, CNR1, HTR2A
lamellipodium 1 AKT1
Cell projection, axon 2 CNR1, HTR2A
Multi-pass membrane protein 2 CNR1, HTR2A
cell cortex 1 AKT1
dendritic shaft 1 HTR2A
glutamatergic synapse 3 AKT1, CNR1, HTR2A
Golgi apparatus 3 ALB, ATRN, PTGS1
Golgi membrane 1 INS
growth cone 1 CNR1
neuronal cell body 1 HTR2A
postsynapse 1 AKT1
presynaptic membrane 2 CNR1, HTR2A
Cytoplasm, cytosol 2 ALOX5, IDO1
Presynapse 2 CNR1, HTR2A
plasma membrane 7 AKT1, ATRN, CNR1, CNR2, F2, HTR2A, TNK1
Membrane 3 AKT1, CAT, TNK1
axon 2 CNR1, HTR2A
caveola 1 HTR2A
extracellular exosome 7 ALB, ATRN, CAT, F2, LYZ, PTGS1, TUBB4B
endoplasmic reticulum 2 ALB, CNR2
extracellular space 6 ALB, ALOX5, ATRN, F2, INS, LYZ
perinuclear region of cytoplasm 2 ALOX5, PPARG
mitochondrion 1 CAT
protein-containing complex 4 AHR, AKT1, ALB, CAT
intracellular membrane-bounded organelle 3 CAT, PPARG, PTGS1
Microsome membrane 1 PTGS1
Single-pass type I membrane protein 1 ATRN
Secreted 3 ALB, F2, INS
extracellular region 7 ALB, ALOX5, CAT, F2, INS, LYZ, TUBB4B
Mitochondrion outer membrane 1 CNR1
mitochondrial outer membrane 1 CNR1
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 1 CAT
anchoring junction 1 ALB
transcription regulator complex 2 AHR, NR1I2
photoreceptor outer segment 1 PTGS1
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
Extracellular vesicle 1 TUBB4B
actin cytoskeleton 1 CNR1
perikaryon 1 CNR2
cytoplasmic vesicle 1 HTR2A
microtubule cytoskeleton 2 AKT1, TUBB4B
cell-cell junction 1 AKT1
vesicle 1 AKT1
postsynaptic membrane 2 CNR2, HTR2A
Cytoplasm, perinuclear region 1 ALOX5
Membrane raft 1 CNR1
Cytoplasm, cytoskeleton 1 TUBB4B
focal adhesion 1 CAT
microtubule 1 TUBB4B
spindle 1 AKT1
GABA-ergic synapse 1 CNR1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 F2
receptor complex 1 PPARG
neuron projection 1 PTGS1
ciliary basal body 2 AKT1, ALB
chromatin 3 AHR, NR1I2, PPARG
stereocilium bundle 1 IDO1
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 2 ALB, F2
[Isoform 3]: Secreted 1 ATRN
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Endomembrane system 1 PTGS1
endosome lumen 1 INS
Membrane, caveola 1 HTR2A
axonemal microtubule 1 TUBB4B
aryl hydrocarbon receptor complex 1 AHR
cell body fiber 1 HTR2A
Cell projection, dendrite 2 CNR2, HTR2A
intermediate filament cytoskeleton 1 NR1I2
ficolin-1-rich granule lumen 2 ALOX5, CAT
secretory granule lumen 3 ALOX5, CAT, INS
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 3 ALB, F2, INS
nuclear matrix 1 ALOX5
platelet alpha granule lumen 1 ALB
specific granule lumen 1 LYZ
tertiary granule lumen 1 LYZ
transport vesicle 1 INS
azurophil granule lumen 2 LYZ, TUBB4B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
neurofilament 1 HTR2A
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
[Isoform 1]: Cell membrane 1 ATRN
catalase complex 1 CAT
Nucleus intermembrane space 1 ALOX5
smooth muscle contractile fiber 1 IDO1
nuclear aryl hydrocarbon receptor complex 1 AHR
G protein-coupled serotonin receptor complex 1 HTR2A
cytosolic aryl hydrocarbon receptor complex 1 AHR
ciliary transition fiber 1 ALB


文献列表

  • Ying Cheng, Xilin Lyu, Chen Liu, Xiancheng Wang, Jing Cheng, Daizhou Zhang, Xiangjing Meng, Yujun Zhao. Synthesis and Biological Evaluation of Sclareolide-Indole Conjugates and Their Derivatives. Molecules (Basel, Switzerland). 2023 Feb; 28(4):. doi: 10.3390/molecules28041737. [PMID: 36838727]
  • Yubo Sun, Hao Wu, Wenning Zhou, Zhichun Yuan, Jianjun Hao, Xili Liu, Lirong Han. Effects of indole derivatives from Purpureocillium lilacinum in controlling tobacco mosaic virus. Pesticide biochemistry and physiology. 2022 May; 183(?):105077. doi: 10.1016/j.pestbp.2022.105077. [PMID: 35430069]
  • Sasikarn Seetasang, Takashi Kaneta. Dip-and-Read, Organic Solvent-Compatible, Paper-Based Analytical Devices Equipped with Chromatographic Separation for Indole Analysis in Shrimp. ACS sensors. 2022 04; 7(4):1194-1200. doi: 10.1021/acssensors.2c00300. [PMID: 35404587]
  • Yujia Wang, Yali Mu, Xiatong Hu, Caixia Zhang, Yanqing Gao, Zhiqing Ma, Juntao Feng, Xili Liu, Peng Lei. Indole/Tetrahydroquinoline as Renewable Natural Resource-Inspired Scaffolds in the Devising and Preparation of Potential Fungicide Candidates. Journal of agricultural and food chemistry. 2022 Apr; 70(15):4582-4590. doi: 10.1021/acs.jafc.1c07879. [PMID: 35385275]
  • Inês Delgado, Sofia Cussotto, Andrea Anesi, Sandra Dexpert, Agnès Aubert, Bruno Aouizerate, Cédric Beau, Damien Forestier, Patrick Ledaguenel, Eric Magne, Fulvio Mattivi, Lucile Capuron. Association between the indole pathway of tryptophan metabolism and subclinical depressive symptoms in obesity: a preliminary study. International journal of obesity (2005). 2022 04; 46(4):885-888. doi: 10.1038/s41366-021-01049-0. [PMID: 35001078]
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  • Vladimír Skalický, Tereza Vojtková, Aleš Pěnčík, Jan Vrána, Katarzyna Juzoń, Veronika Koláčková, Michaela Sedlářová, Martin F Kubeš, Ondřej Novák. Auxin Metabolite Profiling in Isolated and Intact Plant Nuclei. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212369. [PMID: 34830250]
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