Classification Term: 311
Indoles (ontology term: CHEMONTID:0002497)
Compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole." []
found 53 associated metabolites at sub_class metabolite taxonomy ontology rank level.
Ancestor: Indoles and derivatives
Child Taxonomies: 2-phenylindoles, 3-alkylindoles
Camalexin
Camalexin is an indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group. It has a role as a metabolite. It is an indole phytoalexin and a member of 1,3-thiazoles. Camalexin is a natural product found in Arabidopsis, Arabidopsis thaliana, and Camelina sativa with data available. Camalexin is found in fats and oils. Camalexin is an alkaloid from the leaves of Camelina sativa (false flax) infected by the fungus Alternaria brassica Alkaloid from the leaves of Camelina sativa (false flax) infected by the fungus Alternaria brassicae. Camalexin is found in fats and oils. An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group. D000890 - Anti-Infective Agents Camalexin is a phytoalexin isolated from Camelina sativa (Cruciferae) with antibacterial, antifungal, antiproliferative and anticancer activities. Camalexin can induce reactive oxygen species (ROS) production[1][2][3]. Camalexin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=135531-86-1 (retrieved 2024-08-14) (CAS RN: 135531-86-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Indole-3-carboxaldehyde
Indole-3-carboxaldehyde (IAld or I3A), also known as 3-formylindole or 3-indolealdehyde, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of a pyrrole ring fused to benzene to form 2,3-benzopyrrole. In humans, I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells. It stimulates the production of interleukin-22 which facilitates mucosal reactivity (PMID:27102537). I3A is a microbially derived tryptophan metabolite produced by Clostridium and Lactobacillus (PMID:30120222, 27102537). I3A has also been found in the urine of patients with untreated phenylketonuria (PMID:5073866). I3A has been detected, but not quantified, in several different foods, such as beans, Brussels sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make I3A a potential biomarker for the consumption of these foods. Indole-3-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group. It has a role as a plant metabolite, a human xenobiotic metabolite, a bacterial metabolite and a marine metabolite. It is a heteroarenecarbaldehyde, an indole alkaloid and a member of indoles. Indole-3-carboxaldehyde is a natural product found in Euphorbia hirsuta, Derris ovalifolia, and other organisms with data available. A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group. Found in barley and tomato seedlings and cotton Indole-3-carboxaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=487-89-8 (retrieved 2024-07-02) (CAS RN: 487-89-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Indole-3-carboxaldehyde (3-Formylindole), a banlangen extract, is the product of the oxidative degradation of indole-3-acetic acid (IAA) by crude enzyme preparations from etiolated pea seedlings. Indole-3-carboxaldehyde (3-Formylindole) is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin[1]. Indole-3-carboxaldehyde (3-Formylindole), a banlangen extract, is the product of the oxidative degradation of indole-3-acetic acid (IAA) by crude enzyme preparations from etiolated pea seedlings. Indole-3-carboxaldehyde (3-Formylindole) is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin[1].
Pindolol
Pindolol is only found in individuals that have used or taken this drug. It is a moderately lipophilic beta blocker (adrenergic beta-antagonists). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638)Pindolol non-selectively blocks beta-1 adrenergic receptors mainly in the heart, inhibiting the effects of epinephrine and norepinephrine resulting in a decrease in heart rate and blood pressure. By binding beta-2 receptors in the juxtaglomerular apparatus, Pindolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production and therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively. C - Cardiovascular system > C07 - Beta blocking agents > C07A - Beta blocking agents > C07AA - Beta blocking agents, non-selective C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C72900 - Adrenergic Antagonist D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents CONFIDENCE standard compound; INTERNAL_ID 4098 CONFIDENCE standard compound; INTERNAL_ID 2663 Pindolol (LB-46) is a nonselective β-blocker with partial beta-adrenergic receptor agonist activity, also functions as a 5-HT1A receptor weak partial antagonist (Ki=33nM).
Indole
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.
1-Methoxy-1H-indole-3-carboxaldehyde
1-methoxy-1h-indole-3-carboxaldehyde is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. 1-methoxy-1h-indole-3-carboxaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-methoxy-1h-indole-3-carboxaldehyde can be found in root vegetables, which makes 1-methoxy-1h-indole-3-carboxaldehyde a potential biomarker for the consumption of this food product. 1-Methoxy-1H-indole-3-carboxaldehyde is found in root vegetables. 1-Methoxy-1H-indole-3-carboxaldehyde is a stress metabolite from the Japanese radish Daikon (Raphanus sativus var. hortensis) inoculated with Pseudomonas cichorii.
Kaempferol 3-(2'-rhamnosylgalactoside) 7-rhamnoside
Kaempferol 3-(2-rhamnosylgalactoside) 7-rhamnoside is found in broad bean. Kaempferol 3-(2-rhamnosylgalactoside) 7-rhamnoside is isolated from Vicia faba. Isolated from Vicia faba. Kaempferol 3-(2-rhamnosylgalactoside) 7-rhamnoside is found in pulses and broad bean.
Brassilexin
Isolated from leaves of brown mustard (Brassica juncea) (Cruciferae). Brassilexin is found in many foods, some of which are cauliflower, chinese mustard, herbs and spices, and chinese cabbage. Brassilexin is found in brassicas. Brassilexin is isolated from leaves of brown mustard (Brassica juncea) (Cruciferae
Dehydro-4-methoxycyclobrassinin
Dehydro-4-methoxycyclobrassinin is found in brassicas. Dehydro-4-methoxycyclobrassinin is isolated from roots of the turnip Brassica campestris ssp. rapa (Cruciferae) inoculated with Pseudomonas cichorii. Isolated from roots of the turnip Brassica campestris sspecies rapa (Cruciferae) inoculated with Pseudomonas cichorii. Dehydro-4-methoxycyclobrassinin is found in brassicas and root vegetables.
Brassicanal C
Brassicanal C is found in brassicas. Brassicanal C is an alkaloid from Brassica oleracea (cabbage) inoculated with Pseudomonas cichorii. Alkaloid from Brassica oleracea (cabbage) inoculated with Pseudomonas cichorii. Brassicanal C is found in cauliflower and brassicas.
6-Methoxy-3-(2-thiazolyl)-1H-indole
6-Methoxy-3-(2-thiazolyl)-1H-indole is found in fats and oils. 6-Methoxy-3-(2-thiazolyl)-1H-indole is from Camelina sativa (false flax) infected with Alternaria brassicae. From Camelina sativa (false flax) infected with Alternaria brassicae. 6-Methoxy-3-(2-thiazolyl)-1H-indole is found in fats and oils.
Hydroxymethyl indol-3-yl ketone
Hydroxymethyl indol-3-yl ketone is found in mushrooms. Hydroxymethyl indol-3-yl ketone is an alkaloid from liquid cultures of the fungus Lactarius deliciosus. Alkaloid from liquid cultures of the fungus Lactarius deliciosus. Hydroxymethyl indol-3-yl ketone is found in mushrooms.
2,4-Dimethyl-1H-indole
2,4-Dimethyl-1H-indole is found in mushrooms. 2,4-Dimethyl-1H-indole is an alkaloid from fruit bodies of the unpalatable mushrooms Tricholoma sciodes and Tricholoma virgatum. Alkaloid from fruit bodies of the unpalatable mushrooms Tricholoma sciodes and Tricholoma virgatum. 2,4-Dimethyl-1H-indole is found in mushrooms.
Brassicanal B
Brassicanal B is found in brassicas. Brassicanal B is an alkaloid from Chinese cabbage Brassica campestris ssp. pekinensis inoculated with Pseudomonas cichorii. Alkaloid from Chinese cabbage Brassica campestris sspecies pekinensis inoculated with Pseudomonas cichorii. Brassicanal B is found in brassicas.
Indoleacrylic acid
Indoleacrylic acid (CAS: 1204-06-4), also known as indoleacrylate, IA, and IAcrA, is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Indoleacrylic acid is practically insoluble (in water) and a weak acidic compound (based on its pKa). Within the cell, indoleacrylic acid is primarily located in the membrane (predicted from logP). Indoleacrylic acid is best known as a plant growth hormone (a natural auxin), whereas its biological role in animals is still unknown. A two-stage production of this compound is likely: intestinal microorganisms catabolize tryptophan to indole derivatives which are then absorbed and converted into indoleacrylic acid and its glycine conjugate, indolylacryloylglycine (IAcrGly). Indolylacryloylglycine excretion in urine is especially pronounced in some myopathies, namely in boys with Duchenne muscular dystrophy (PMID: 10707769). It has been recently found that indoleacrylic acid promotes intestinal epithelial barrier function and mitigates inflammatory responses. Stimulating indoleacrylic acid production could promote anti-inflammatory responses and have therapeutic benefits (PMID: 28704649). Urinary Indole-3-acrylate is produced by Clostridium sporogenes (PMID: 29168502). Indoleacrylic acid is also a metabolite of Peptostreptococcus (PMID: 28704649, 29168502). trans-3-Indoleacrylic acid is an endogenous metabolite.
Cyclobrassinone
Cyclobrassinone is found in brassicas. Cyclobrassinone is isolated from Brassica oleracea var. gongylodes (kohlrabi). Isolated from Brassica oleracea variety gongylodes (kohlrabi). Cyclobrassinone is found in brassicas.
Brassicanal A
Alkaloid from Chinese cabbage (Brassica campestris sspecies pekinensis) inoculated with Pseudomonas cichorii. Brassicanal A is found in many foods, some of which are chinese cabbage, brassicas, cauliflower, and radish. Brassicanal A is found in brassicas. Brassicanal A is an alkaloid from Chinese cabbage (Brassica campestris ssp. pekinensis) inoculated with Pseudomonas cichorii.
2-Bromo-1H-indole-3-carboxaldehyde
2-Bromo-1H-indole-3-carboxaldehyde is a plant growth enhancer for rice. Plant growth enhancer for rice. Prob. of no coml. significance
4-(2-Hydroxy-3-(tert-butylamino)propoxy)-3-iodo-1H-indole-2-carbonitrile
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists
(E)-3-(2-(1H-Tetrazol-5-YL)vinyl)-6-fluoro-1H-indole
1-[(5-Methoxy-3-indolylidene)methylamino]-2-pentylguanidine
Besipirdine
C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist
Cyanopindolol
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists
Cypridina luciferin
1H-Indole-2-carbonitrile, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-3-iodo-
3-[(2Z,3E)-3-(Hydroxyimino)-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one
Mepindolol
C - Cardiovascular system > C07 - Beta blocking agents > C07A - Beta blocking agents > C07AA - Beta blocking agents, non-selective C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C72900 - Adrenergic Antagonist D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists
5-Methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
2-(1H-Indol-2-ylmethyl)-1H-indole
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents
1-[[(Z)-[5-(Hydroxymethyl)indol-3-ylidene]methyl]amino]-2-pentylguanidine
Rutalexin
Rutalexin is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Rutalexin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Rutalexin can be found in chinese cabbage, which makes rutalexin a potential biomarker for the consumption of this food product.
Rapalexin A
Rapalexin a is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Rapalexin a is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Rapalexin a can be found in chinese cabbage, which makes rapalexin a a potential biomarker for the consumption of this food product.
