MiMeDB: Showing metabocard for Indole (MMDBc0000004)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:37 UTC

Update Date

2024-09-28 00:55:51 UTC

Metabolite ID

MMDBc0000004

Metabolite Identification

Common Name

Indole

Description

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
2,3-Benzopyrrole	ChEBI
indol	ChEBI
1-Azaindene	HMDB
1-Benzazole	HMDB
Benzo[b]pyrrole	HMDB
Ketole	HMDB
Indole	HMDB

Molecular Formula

C₈H₇N

Average Mass

117.1479

Monoisotopic Mass

117.057849229

IUPAC Name

1H-indole

Traditional Name

indole

CAS Registry Number

120-72-9

SMILES

N1C=CC2=C1C=CC=C2

InChI Identifier

InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

InChI Key

SIKJAQJRHWYJAI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole (CHEBI:16881 )
polycyclic heteroarene (CHEBI:16881 )
an indole (INDOLE )

Functional Ontology

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Lower GI Disorder

Ulcerative colitis (PMID: 23867873 , PMID: 21761941 , PMID: 25037050 , +78

Source	Link
Pubmed	PMID: 23867873
Pubmed	PMID: 21761941
Pubmed	PMID: 25037050
Pubmed	PMID: 24010549
Pubmed	PMID: 20809621
Pubmed	PMID: 27543620
Pubmed	PMID: 24029555
Pubmed	PMID: 25985090
Pubmed	PMID: 18085514
Pubmed	PMID: 21330412
Pubmed	PMID: 29808030
Pubmed	PMID: 28029051
Pubmed	PMID: 28842642
Pubmed	PMID: 27065191
Pubmed	PMID: 25670064
Pubmed	PMID: 21761941
Pubmed	PMID: 28842642
Pubmed	PMID: 19167006
Pubmed	PMID: 26806034
Pubmed	PMID: 23454028
Pubmed	PMID: 24811995
Pubmed	PMID: 6740214
Pubmed	PMID: 21494609
Pubmed	PMID: 23997757
Pubmed	PMID: 17314143
Pubmed	PMID: 25479871
Pubmed	PMID: 24922509
Pubmed	PMID: 26806034
Pubmed	PMID: 24811995
Pubmed	PMID: 25486321
Pubmed	PMID: 19573517
Pubmed	PMID: 18052033
Pubmed	PMID: 27609529
Pubmed	PMID: 26709303
Pubmed	PMID: 20669995
Pubmed	PMID: 19006102
Pubmed	PMID: 27622378
Pubmed	PMID: 17269711
Pubmed	PMID: 27624970
Pubmed	PMID: 27107423
Pubmed	PMID: 25598765
Pubmed	PMID: 26416813
Pubmed	PMID: 23940645
Pubmed	PMID: 28270806
Pubmed	PMID: 21190195
Pubmed	PMID: 22308371
Pubmed	PMID: 17269711
Pubmed	PMID: 28270806
Pubmed	PMID: 28587349
Pubmed	PMID: 19259987
Pubmed	PMID: 25598765
Pubmed	PMID: 23940645
Pubmed	PMID: 19636438
Pubmed	PMID: 22411374
Pubmed	PMID: 24375085
Pubmed	PMID: 23857558
Pubmed	PMID: 25037050
Pubmed	PMID: 31026179
Pubmed	PMID: 27609529
Pubmed	PMID: 21970810
Pubmed	PMID: 20055983
Pubmed	PMID: 14684577
Pubmed	PMID: 30944877
Pubmed	PMID: 21386183
Pubmed	PMID: 24130822
Pubmed	PMID: 24922509
Pubmed	PMID: 22944170
Pubmed	PMID: 24421258
Pubmed	PMID: 21280206
Pubmed	PMID: 26848182
Pubmed	PMID: 22435727
Pubmed	PMID: 20300169
Pubmed	PMID: 28587349
Pubmed	PMID: 20300169
Pubmed	PMID: 24657864
Pubmed	PMID: 24628373
Pubmed	PMID: 12097436
Pubmed	PMID: 21494186
Pubmed	PMID: 21190195
Pubmed	PMID: 24246267
Pubmed	PMID: 17314143

)

Disposition

Biological location

Non-excretory biofluid

Blood
Saliva

Excreta

Feces
Urine

Tissue

Epithelium

Epidermis

Organ

Intestine

Cell

Neuron

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Nuts

Cocoa and cocoa products

Cocoa

Cocoa bean

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.31 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.07	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	16.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.14 m³·mol⁻¹	ChemAxon
Polarizability	12.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-6900000000-09af4d0af4e5f7259a59	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9800000000-4160749bd673d5e00048	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9800000000-33bf321019a6a8e3401a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-6900000000-09af4d0af4e5f7259a59	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9800000000-4160749bd673d5e00048	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9800000000-33bf321019a6a8e3401a	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-7900000000-2a9e4ccc61fee73a480e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-622dfed80152ea08d52a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9100000000-2531cceca05522a5489e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-5e07c15293929ff4440f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (MX-1303) , Positive	splash10-014i-6900000000-09af4d0af4e5f7259a59	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-014i-9800000000-4160749bd673d5e00048	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-014i-9800000000-33bf321019a6a8e3401a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-0900000000-e6b11e225744a0d85f71	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-e6b11e225744a0d85f71	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-0900000000-7b49c1c370d7355c5e6f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-050ef45f3ec404d7eb65	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-79ff95be504a5efad264	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-31ff8b484e0dc207fcc9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-864a48552fea562fc370	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-0900000000-bd82bfab4567619b5c41	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-0900000000-6bff353534e6f5f9105b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-0900000000-c4e339d4a1d3fda0a949	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-2900000000-100cd0cc67ac9eda3f4e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014l-5900000000-79447b563349d08aacc0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00kf-9800000000-a1ce5da5416e6d003ff9	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-aba5022e03d31dcbcc86	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-78c0f569df5b7f51c52c	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-6900000000-bacb6e9a65a688229f96	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-e93b2f48040666dd7fe0	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-07d8a93ec0ace38ef3b3	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-6900000000-8abfc9b162cc93f153ac	2016-09-14	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-9700000000-3b1ec48b5bce79adb282	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)		2016-10-22	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Epidermis
Feces
Fibroblasts
Intestine
Neuron
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank
Metabolism and Physiological Effects of Indoxyl Sulfate

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0006139	Indole	Indoxyl	cytochrome P450, family 2, subfamily E, polypeptide 1	VMH	30371894
MMDBr0006979	L-Tryptophan	Indole	Not Available	VMH	30371894
MMDBr0007585	Indole	L-Tryptophan	Not Available	VMH	30371894
MMDBr0010964	L-Tryptophan	Indole	Not Available	VMH	30371894
MMDBr0012657	Indole	L-Tryptophan	Not Available	VMH	30371894

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012716	L-Tryptophan	Indole	Tryptophanase			23397453
MMDBr0012717	Indole	Indoxyl	CYP2E1	oxidation	PubMed	11808865
MMDBr0012719	Indoxyl	Indoxyl sulfate	sulfotransferase family, cytosolic, 1A, phenol-preferring, member 1	Indoxyl Sulfate Formation from Indoxyl	RHEA; KEGG; VMH	11808865

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012716	L-Tryptophan	Indole	Tryptophanase			23397453
MMDBr0012717	Indole	Indoxyl	CYP2E1	oxidation	PubMed	11808865
MMDBr0012720	Indoxyl	Indoxyl glucuronide	Not Available	conjugation; phase-II biotransformation; glucuronide-conjugation		Manually annotated by MiMeDB team

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Celiac disease		Association	Human Feces	HMDB	21970810
Crohn's disease		Association	Human Feces	HMDB	23867873
Irritable bowel syndrome		Association	Human Feces	HMDB	23867873
Ulcerative colitis		Association	Human Feces	HMDB	23867873
Atherosclerosis	decreased	Association	Human plasma	PubMed	29248242
Crohn's disease	decreased	Association	Human wet feces	HMDB	24811995
Ulcerative colitis	decreased	Association	Human wet feces	HMDB	24811995
Clostridium difficile infection	increased	Association	Human wet feces	PubMed	30986230
Aryl hydrocarbon receptor	agonist	Cell culture	House mouse CaCo-2 intestinal cells	PubMed	24563545
Anti-inflammatory		Animal_model	liver	PubMed	29906245
Aryl hydrocarbon receptor	agonist	Cell culture	House mouse AZ-AHR cells (HepG2)	PubMed	32283770
Oxidative stress	induces	Cell culture	HL-60 human macrophage cell	PubMed	32879256
Phagocytic activity	impairs	Cell culture	HL-60 human macrophage cell	PubMed	32879256

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	122	Human saliva; Human feces; Human stool; Human urine; Human ; Human appendix biopsy; Human subgingival plaque; Human bronichial aspirate; Human sputum; bal; Human gastric fluid; Human supragingival plaque	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	295	Human feces; Human urine; Human ; Human unknown; Human vaginal fluid; Human stool; Human vaginal secretion; Human supragingival plaque; Human saliva; Human mucosa; Human subgingival plaque; Human pleural fluid plaque; Pig	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Fusobacteria	23	Human feces; Human ; Human saliva; bal; Human supragingival plaque; Human saliva; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	218	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; River trout ; Chicken	Microbial culture; Metabolic reconstruction
Bacteria	Spirochaetes	4	Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	106	Human feces; Human ; Human pleural fluid plaque; Human dental plaque; Human sputum; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	2		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Coffee	Coffea arabica	PubMed	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	14684577
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Campylobacter jejuni infection	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Clostridium difficile infection	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative Colitis	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20055983
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21386183
Human Feces	Detected but not Quantified						Newborn (0-30 days old)	Both	Normal	HMDB	21386183
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	21494609
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	Normal	HMDB	21970810
Human Feces	Detected and Quantified			0	132368.285	nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	HMDB	21970810
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22284503
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Breast cancer	HMDB	22284503
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	HMDB	23454028
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected and Quantified	0.00108		0.000478	0.00501	nmol/g wet feces	Not Specified	Not Specified	Crohns disease	HMDB	23867873
Human Feces	Detected and Quantified	0.00023		0.000111	0.00139	nmol/g wet feces	Not Specified	Not Specified	Ulcerative colitis	HMDB	23867873
Human Feces	Detected and Quantified	0.00035		0.000068	0.000999	nmol/g wet feces	Not Specified	Not Specified	Irritable bowel syndrome	HMDB	23867873
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Crohn's disease	HMDB	23867873
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Ulcerative colitis	HMDB	23867873
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Autism	HMDB	24130822
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	HMDB	24130822
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	24130822
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative colitis	HMDB	24811995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Crohn's disease	HMDB	24811995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24811995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) non progressor	HMDB	24922509
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) progressor	HMDB	24922509
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24922509
Human Feces	Detected and Quantified	32352.266				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	11962.0867				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	23400.619				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Crohns disease	HMDB	26806034
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative colitis	HMDB	26806034
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26806034
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Feces	Detected and Quantified	762.8	53.8			uM	Not Specified	Not Specified	non-Clostridium difficile diarrhea	HMDB	30944877
Human Feces	Detected and Quantified	1684	84.4			uM	Not Specified	Not Specified	Clostridium difficile infection	HMDB	30944877
Human Feces	Detected and Quantified	300	6640			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	30944877
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Clostridium difficile infection	HMDB	30986230
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Feces	Detected and Quantified			0	132368.285	nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	HMDB	21970810
Human Feces	Detected and Quantified	1684.0	84.4			uM	Not Specified	Not Specified	Clostridium difficile infection	HMDB	30944877
Human Feces	Detected and Quantified	0.00108		0.000478	0.00501	nmol/g wet feces	Not Specified	Not Specified	Crohns disease	HMDB	23867873
Human Feces	Detected and Quantified	0.000350		0.000068	0.000999	nmol/g wet feces	Not Specified	Not Specified	Irritable bowel syndrome	HMDB	23867873
Human Feces	Detected and Quantified	0.000230		0.000111	0.00139	nmol/g wet feces	Not Specified	Not Specified	Ulcerative colitis	HMDB	23867873
Human Feces	Detected and Quantified	11962.0867				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	23400.619				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	32352.266				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	300	6640			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	30944877
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22284503
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20055983
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21386183
Human Feces	Detected but not Quantified						Newborn (0-30 days old)	Both	Normal	HMDB	21386183
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	21494609
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	Normal	HMDB	21970810
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	24130822
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24811995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24922509
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26806034
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	14684577
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000738

DrugBank ID

DB04532

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Indole

METLIN ID

286

PubChem Compound

798

PDB ID

Not Available

ChEBI ID

16881

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gambhir KK, McMenamy RH, Watson F: Positions in human serum albumin which involve the indole binding site. Sequence of 107-residue fragment. J Biol Chem. 1975 Sep 10;250(17):6711-9. [PubMed:1158878 ]
Welch DF, Ahlin PA, Matsen JM: Differentiation of Haemophilus spp. in Respiratory isolate cultures by an indole spot test. J Clin Microbiol. 1982 Feb;15(2):216-9. doi: 10.1128/jcm.15.2.216-219.1982. [PubMed:7040445 ]
Kunka RL, Hussey EK, Shaw S, Warner P, Aubert B, Richard I, Fowler PA, Pakes GE: Safety, tolerability, and pharmacokinetics of sumatriptan suppositories following single and multiple doses in healthy volunteers. Cephalalgia. 1997 Jun;17(4):532-40. doi: 10.1046/j.1468-2982.1997.1704532.x. [PubMed:9209775 ]
Scott AK: Sumatriptan clinical pharmacokinetics. Clin Pharmacokinet. 1994 Nov;27(5):337-44. doi: 10.2165/00003088-199427050-00002. [PubMed:7851052 ]
Coowar D, Bouissac J, Hanbali M, Paschaki M, Mohier E, Luu B: Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres. J Med Chem. 2004 Dec 2;47(25):6270-82. doi: 10.1021/jm0493616. [PubMed:15566297 ]
Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. doi: 10.1128/jcm.28.10.2220-2223.1990. [PubMed:2229345 ]
Agatsuma S, Sekino H, Watanabe H: Indoxyl-beta-D-glucuronide and 3-indoxyl sulfate in plasma of hemodialysis patients. Clin Nephrol. 1996 Apr;45(4):250-6. [PubMed:8861801 ]
Aoyama I, Miyazaki T, Niwa T: Preventive effects of an oral sorbent on nephropathy in rats. Miner Electrolyte Metab. 1999 Jul-Dec;25(4-6):365-72. doi: 10.1159/000057476. [PubMed:10681668 ]
Cooke M, Leeves N, White C: Time profile of putrescine, cadaverine, indole and skatole in human saliva. Arch Oral Biol. 2003 Apr;48(4):323-7. doi: 10.1016/s0003-9969(03)00015-3. [PubMed:12663078 ]
Yoshida M, Mishiro Y: [Indole production in human whole saliva]. Shigaku. 1989 Aug;77(2):472-86. [PubMed:2489307 ]
Freedman DX, Belendiuk K, Belendiuk GW, Crayton JW: Blood tryptophan metabolism in chronic schizophrenics. Arch Gen Psychiatry. 1981 Jun;38(6):655-9. doi: 10.1001/archpsyc.1981.01780310055005. [PubMed:7247628 ]
Takken W, van Loon JJ, Adam W: Inhibition of host-seeking response and olfactory responsiveness in Anopheles gambiae following blood feeding. J Insect Physiol. 2001 Mar;47(3):303-310. doi: 10.1016/s0022-1910(00)00107-4. [PubMed:11119776 ]
Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
Claus G, Kutzner HJ: Degradation of indole by Alcaligenes spec. Syst Appl Microbiol. 1983;4(2):169-80. doi: 10.1016/S0723-2020(83)80046-0. [PubMed:23194589 ]
Kamath AV, Vaidyanathan CS: New pathway for the biodegradation of indole in Aspergillus niger. Appl Environ Microbiol. 1990 Jan;56(1):275-80. doi: 10.1128/aem.56.1.275-280.1990. [PubMed:2310183 ]
Doukyu N, Aono R: Biodegradation of indole at high concentration by persolvent fermentation with Pseudomonas sp. ST-200. Extremophiles. 1997 May;1(2):100-5. doi: 10.1007/s007920050021. [PubMed:9680309 ]
Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]
Kim J, Park W: Indole: a signaling molecule or a mere metabolic byproduct that alters bacterial physiology at a high concentration? J Microbiol. 2015 Jul;53(7):421-8. doi: 10.1007/s12275-015-5273-3. Epub 2015 Jun 27. [PubMed:26115989 ]
Kumar A, Sperandio V: Indole Signaling at the Host-Microbiota-Pathogen Interface. mBio. 2019 Jun 4;10(3). pii: mBio.01031-19. doi: 10.1128/mBio.01031-19. [PubMed:31164470 ]

Showing metabocard for Indole (MMDBc0000004)

MOL for #<Metabolite:0x00007f46d485f4e0>

3D MOL for #<Metabolite:0x00007f46d485f4e0>

3D SDF for #<Metabolite:0x00007f46d485f4e0>

3D-SDF for #<Metabolite:0x00007f46d485f4e0>

PDB for #<Metabolite:0x00007f46d485f4e0>

3D PDB for #<Metabolite:0x00007f46d485f4e0>

SMILES for #<Metabolite:0x00007f46d485f4e0>

INCHI for #<Metabolite:0x00007f46d485f4e0>

Structure for #<Metabolite:0x00007f46d485f4e0>

3D Structure for #<Metabolite:0x00007f46d485f4e0>