Indole (Compound)

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ID	1868
Name	Indole
Synonyms	1H-Indole; 2,3-Benzopyrole
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE001868 (Indole) 3D Structure for EE001868 (Indole) 798 -OEChem-09232116023D 16 17 0 0 0 0 0 0 0999 V2000 1.5610 1.1123 -0.0001 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2536 0.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2815 -0.7155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6500 -1.1056 0.0002 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9394 1.4123 -0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9396 -1.4182 -0.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4121 0.0399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1383 0.6938 0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1409 -0.6998 0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8497 2.0807 -0.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0368 -2.1155 0.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9385 2.4972 -0.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9561 -2.5043 -0.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4829 0.1869 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0829 1.2317 0.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0859 -1.2365 0.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 7 1 0 0 0 0 1 10 1 0 0 0 0 2 3 1 0 0 0 0 2 5 2 0 0 0 0 3 4 1 0 0 0 0 3 6 2 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 798 > <PUBCHEM_CONFORMER_RMSD> 0.4 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 15 1 0.03 10 0.27 11 0.15 12 0.15 13 0.15 14 0.15 15 0.15 16 0.15 2 -0.15 4 -0.15 5 -0.15 6 -0.15 7 -0.3 8 -0.15 9 -0.15 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 0 > <PUBCHEM_PHARMACOPHORE_FEATURES> 4 1 1 cation 1 1 donor 5 1 2 3 4 7 rings 6 2 3 5 6 8 9 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 9 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 1 > <PUBCHEM_CONFORMER_ID> 0000031E00000001 > <PUBCHEM_MMFF94_ENERGY> 14.2706 > <PUBCHEM_FEATURE_SELFOVERLAP> 20.389 > <PUBCHEM_SHAPE_FINGERPRINT> 12897270 3 18410574015237340884 16945 1 18410573985167307878 18185500 45 18266457796448572079 21040471 1 18338516331047356036 23402655 69 18195790887948552341 23552423 10 18260833700078273294 2748010 2 18410573998073282959 29004967 10 18334299811286793707 369184 2 18410569578525594035 5084963 1 18272368637773214299 > <PUBCHEM_SHAPE_MULTIPOLES> 180.23 3.06 1.53 0.61 0.3 0.01 0 0 0 -0.22 0 -0.01 0.01 0 > <PUBCHEM_SHAPE_SELFOVERLAP> 398.193 > <PUBCHEM_SHAPE_VOLUME> 98.7 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	Microbial metabolite identified in gut (table 1 from Donia 2015). Metabolite of tryptophan, produced by bacteria (Fig 2, pmid:29902437). Gut microbiota metabolite of tryptophan (Fig 1, pmid:30120222). Prominent metabolite of tryptophan.
Classification	Compounds > Chemical entities > Organic compounds > Organoheterocyclic compounds > Indoles and derivatives > Indoles
CAS number	120-72-9
PubChem ID	798
ChEBI ID	16881
FooDB ID	FDB012008
HMDB ID	HMDB0000738

Chemical data

MolDBi data

IUPAC Name	1H-indole
Traditional IUPAC Name	indole
Formula	C8H7N
InChI	InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
InChI Key	SIKJAQJRHWYJAI-UHFFFAOYSA-N
Molecular weight	117.1479
Exact mass	117.057849229
SMILES	N1C=CC2=C1C=CC=C2

ClassyFire 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	Benzenoids Pyrroles Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives

Publications with Indole

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of Indole in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of Indole with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of Indole with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of Indole exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of Indole exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication