indoxyl profile

Indoxyl is an organic compound with the formula C8H7NO. It is a colorless solid that is soluble in water. Indoxyl is an important intermediate in the biosynthesis of indigo, a blue dye. It is also a component of urine, where it is formed from the breakdown of tryptophan. Indoxyl is produced by the reaction of indole with oxygen. Indoxyl is a precursor to indican, a compound that gives urine its characteristic yellow color. Indoxyl is also a potent inducer of oxidative stress and inflammation. Studies have shown that high levels of indoxyl sulfate, a conjugated form of indoxyl, are associated with an increased risk of cardiovascular disease, chronic kidney disease, and other health problems. As a result, there is growing interest in understanding the role of indoxyl in human health and disease.'

3-hydroxyindole: inhibits amyloid fibril formation; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	50591
CHEBI ID	17840
SCHEMBL ID	155191
SCHEMBL ID	156061
MeSH ID	M0105261

Synonym
CHEBI:17840
C05658
480-93-3
1h-indol-3-ol
indoxyl ,
indole-3-ol
3-hydroxyindole
indole, 3-hydroxy-
9BD3B4C3-E69E-4F14-BFCE-5F97BCB1C030
AKOS006351675
69594-78-1
1h-indolol
A827466
FT-0607900
AB12538
SCHEMBL155191
SCHEMBL156061
PCKPVGOLPKLUHR-UHFFFAOYSA-N
1,2-dihydro-indol-3-one
J-512648
ZB1041
Q423256
F18139
PS-11811
3-hydroxy-1h-indole
AMY32890
DTXSID20861998
CS-0323080
PD000665

Excerpt	Reference	Relevance
"Indoxyl is a highly fluorescent intermediate in the conversion of indole to indigo by Tod."	( The measurement of toluene dioxygenase activity in biofilm culture of Pseudomonas putida F1. Cox, CD; Robinson, KG; Sanseverino, J; Sayler, GS; Woo, Hj, 2000)	1.03

Excerpt	Reference	Relevance
"In this work we describe the conditional toxic effect of the expression of enzymes that cleave 5-bromo-4-chloro-3-indolyl (BCI) substrates and its use as a new counterselection principle useful for the generation of clean and unmarked mutations in the genomes of bacteria."	( Toxicity of indoxyl derivative accumulation in bacteria and its use as a new counterselection principle. Angelov, A; Geissler, A; Leis, B; Li, H; Liebl, W, 2013)	0.77

Class	Description
hydroxyindoles	Any member of the class of indoles carrying at least one hydroxy group.
heteroaryl hydroxy compound	Any organic aromatic compound having one or more hydroxy groups attached to a heteroarene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
indigo biosynthesis	0	8
indican biosynthesis	0	10
indican biosynthesis	0	11
indigo biosynthesis	0	9

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	21 (41.18)	18.7374
1990's	3 (5.88)	18.2507
2000's	8 (15.69)	29.6817
2010's	13 (25.49)	24.3611
2020's	6 (11.76)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (1.82%)	6.00%
Case Studies	1 (1.82%)	4.05%
Observational	1 (1.82%)	0.25%
Other	52 (94.55%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.01	1	hydroxytryptophan	human metabolite; neurotransmitter
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.01	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	1.98	1	N-acylglycine	human blood serum metabolite; uremic toxin
indole [no description available]	8.45	8	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.42	2	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	1.98	1	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.33	2	sulfur oxoacid	catalyst
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	2.03	1	indolyl alcohol	antineoplastic agent; plant metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.08	1	lactose
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.49	2	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	2.01	1	monoterpenoid; phenols	volatile oil component
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	2	1	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
zephiramine [no description available]	2.01	1
thiazoles [no description available]	1.97	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
indirubin [no description available]	2	1
indoline indoline: structure given in first source	2.53	2	indoles
silver acetate silver acetate: RN refers to acetic acid, silver (1+) salt	2.11	1
indoxyl acetate [no description available]	1.93	1	indoles
fucose Fucose: A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.. L-fucopyranose : The pyranose form of L-fucose.. fucose : Any deoxygalactose that is deoxygenated at the 6-position.	2.08	1	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
azo rubin s azo rubin S: RN given refers to parent cpd; structure	2.33	2
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.01	1	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	1.96	1	metal sulfate	emetic; fertilizer; sensitiser
potassium sulfate potassium sulfate: RN given refers to cpd with MF of K2-H2SO4	1.93	1	inorganic potassium salt; potassium salt
indoxyl phosphate indoxyl phosphate: RN given refers to parent cpd	6.96	1
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.37	2	benzenes; phenyl acetates
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.17	1	D-glucopyranose	epitope; mouse metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	6.97	1	organic bromide salt	colorimetric reagent; dye
5-bromo-4-chloro-3-indoxyl phosphate 5-bromo-4-chloro-3-indoxyl phosphate: substrate for demonstration of activity of alkaline phosphatase; structure given in first source. 5-bromo-4-chloro-3-indolyl phosphate : An aryl phosphate that is indoxyl phopshate in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for the presence of an enzyme, alkaline phosphatase, which cleaves the phosphate group to give 5-bromo-4-chloroindoxyl, which immediately dimerises to give an intensely blue product.	2.03	1	aryl phosphate; indoles; organobromine compound; organochlorine compound	chromogenic compound
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	2.21	1	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
4-hydroxyindole hydroxyindoles : Any member of the class of indoles carrying at least one hydroxy group.	2.03	1	hydroxyindoles; phenols
indican, plant indican, plant: RN given refers to the (D-Glu)-isomer	2.17	1
tetranitrotetrazolium blue [no description available]	1.97	1
dansylsarcosine [no description available]	1.98	1
3-carboxy-4-methyl-5-propyl-2-furanpropionic acid 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid: structure in first source. 2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid : A furoic acid that is furan-3-carboxylic acid substituted by a methyl group at position 4, a propyl group at position 5 and a 2-carboxyethyl group at position 2. It is a potent uremic toxin that has been found to accumulate in human serum of patients with chronic kidney diseases.	1.98	1	dicarboxylic acid; furoic acid	human metabolite; uremic toxin
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.08	1	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
indican [no description available]	3.61	9	beta-D-glucoside; exopolysaccharide; indolyl carbohydrate
glycosides [no description available]	3.82	3
n-acetylneuraminoyllactose [no description available]	2.08	1
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	3.18	5
indoxyl glucuronide indoxyl glucuronide: substrate for the detection of E coli in urine	2.6	1	glucosiduronic acid
minfiensine minfiensine: structure in first source	2.11	1
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	1.97	1
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.37	2
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
aza-pinacol aza-pinacol: structure in first source	2.11	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.01	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	1.98	1	benzenes; hydroxycoumarin; methyl ketone
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	6.93	1

Condition	Relationship Strength	Studies
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.63	2
Aortic Stenosis [description not available]	2.6	1
Calcification, Pathologic [description not available]	2.6	1
Aortic Valve Stenosis A pathological constriction that can occur above (supravalvular stenosis), below (subvalvular stenosis), or at the AORTIC VALVE. It is characterized by restricted outflow from the LEFT VENTRICLE into the AORTA.	2.6	1
Calcinosis Pathologic deposition of calcium salts in tissues.	2.6	1
Malnourishment [description not available]	2.31	1
Chronic Kidney Diseases [description not available]	2.31	1
Malnutrition An imbalanced nutritional status resulting from insufficient intake of nutrients to meet normal physiological requirement.	7.31	1
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.31	1
Sarcopenia Progressive decline in muscle mass due to aging which results in decreased functional capacity of muscles.	7.31	1
Cardiac Failure [description not available]	2.15	1
Blood Pressure, High [description not available]	2.15	1
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.15	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.15	1
Allergic Reaction [description not available]	2.11	1
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.11	1
Experimental Leukemia [description not available]	6.93	1
Ureteral Diseases Pathological processes involving the URETERS.	1.93	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	1.93	1
Uremia A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.	1.98	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.97	1
Infant, Newborn, Diseases Diseases of newborn infants present at birth (congenital) or developing within the first month of birth. It does not include hereditary diseases not manifesting at birth or within the first 30 days of life nor does it include inborn errors of metabolism. Both HEREDITARY DISEASES and METABOLISM, INBORN ERRORS are available as general concepts.	1.97	1
Dermatoses [description not available]	1.97	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	1.97	1
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	1.97	1
Plasmodium falciparum Malaria [description not available]	2.05	1
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.05	1

indoxyl

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Research Demand Index: 61.75

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