Indoxyl sulfate (Compound)

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ID	1869
Name	Indoxyl sulfate
Synonyms	3-Indoxyl sulfate; 3-Indoxylsulfuric acid; Indican
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE001869 (Indoxyl sulfate) 3D Structure for EE001869 (Indoxyl sulfate) 10258 -OEChem-09232115593D 21 22 0 0 0 0 0 0 0999 V2000 -2.9905 -0.1512 0.0098 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.4351 -0.6819 0.0068 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8482 -1.5266 -0.1672 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 0.6482 -1.1826 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2892 0.3793 1.3271 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9191 1.9237 0.0022 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0194 -0.3050 0.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7915 0.8587 0.0005 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3450 0.0992 0.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3742 1.4748 0.0049 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6736 -1.5530 0.0005 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1908 0.8367 -0.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0728 -1.5903 -0.0023 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8176 -0.4126 -0.0038 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1946 2.8961 0.0025 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1874 2.1867 0.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1057 -2.4790 0.0016 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7716 1.7530 -0.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5828 -2.5500 -0.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9034 -0.4650 -0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8273 -1.4132 -0.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 1 4 2 0 0 0 0 1 5 2 0 0 0 0 2 9 1 0 0 0 0 3 21 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 9 10 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 10258 > <PUBCHEM_CONFORMER_RMSD> 0.6 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 5 4 2 3 6 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 20 1 1.67 10 -0.3 11 -0.15 12 -0.15 13 -0.15 14 -0.15 15 0.27 16 0.15 17 0.15 18 0.15 19 0.15 2 -0.25 20 0.15 21 0.5 3 -0.68 4 -0.65 5 -0.65 6 0.03 8 -0.15 9 0.06 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 2 > <PUBCHEM_PHARMACOPHORE_FEATURES> 8 1 3 acceptor 1 4 acceptor 1 5 acceptor 1 6 cation 1 6 donor 4 1 3 4 5 anion 5 6 7 8 9 10 rings 6 7 8 11 12 13 14 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 14 > <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> 0000281200000001 > <PUBCHEM_MMFF94_ENERGY> 22.7043 > <PUBCHEM_FEATURE_SELFOVERLAP> 40.745 > <PUBCHEM_SHAPE_FINGERPRINT> 10219947 1 18413389834688719838 10980938 120 18410574011290617510 11132069 177 18411973663870445482 11471102 20 18409725166686131316 11543360 7 15719690808885009582 11769659 78 18409444752518902378 11806522 49 18339921640120426143 12032990 46 18410858737510118006 13296908 3 18334293145550336607 13571099 22 18410848841815758389 14144814 61 18343584036021816867 14251717 144 18410853291296609230 14252887 29 18060146431430373950 14576447 43 18199459042583539103 15219456 202 18261106365918771940 15375462 189 18335143063706957683 15477762 27 18338515347526323071 15501101 241 18408604777296409812 16945 1 18410855473335122384 17844478 74 17894917312754731485 18186145 218 18408889511958008790 19422 9 18272375277787495959 200 152 18131061680469143735 20201158 50 18334294253715358498 20279233 1 17894910728548728707 20281407 28 18335983094932745336 20281475 54 18412267203209895358 20645477 70 18337946792714739071 20871998 22 18199476467508334918 21501502 16 18266744567531519288 21501925 9 18412819209470569562 221490 88 18191592062540599659 23402539 116 17967805038335244430 23402655 69 18410568470666813445 23463225 33 18411983542158037174 23559900 14 18192420884555950842 2748010 2 18194675969787301220 53428517 54 18411136931052725646 581208 293 18411416233023735544 77492 1 17703791422543123009 8809292 202 18186808005922759291 > <PUBCHEM_SHAPE_MULTIPOLES> 263.5 6.79 1.69 0.77 3.02 0.01 -0.04 -1.85 0.01 -0.51 0.04 0.56 0.07 -0.01 > <PUBCHEM_SHAPE_SELFOVERLAP> 561.43 > <PUBCHEM_SHAPE_VOLUME> 148.3 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	Microbial metabolite of indole found in human urine (Donia 2015). A well-known uremic toxin.
Classification	Compounds > Chemical entities > Organic compounds > Organic acids and derivatives > Organic sulfuric acids and derivatives > Arylsulfates
CAS number	487-94-5
PubChem ID	10258
ChEBI ID	43355
FooDB ID	FDB022179
HMDB ID	HMDB0000682

Chemical data

MolDBi data

IUPAC Name	(1H-indol-3-yl)oxidanesulfonic acid
Traditional IUPAC Name	3-sulfooxy-1H-indole
Formula	C8H7NO4S
InChI	InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)
InChI Key	BXFFHSIDQOFMLE-UHFFFAOYSA-N
Molecular weight	213.21
Exact mass	213.009578407
SMILES	OS(=O)(=O)OC1=CNC2=CC=CC=C12

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Organic sulfuric acids and derivatives
Sub Class	Arylsulfates
Direct Parent	Arylsulfates
Alternative Parents	Indoles Sulfuric acid monoesters Substituted pyrroles Benzenoids Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives

Publications with Indoxyl sulfate

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 Indoxyl sulfate 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 Indoxyl sulfate 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 Indoxyl sulfate 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 Indoxyl sulfate 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 Indoxyl sulfate 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