MiMeDB: Showing metabocard for Indoxyl sulfate (MMDBc0000001)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-12-11 00:18:36 UTC

Update Date

2024-10-11 04:59:25 UTC

Metabolite ID

MMDBc0000001

Metabolite Identification

Common Name

Indoxyl sulfate

Description

Indoxyl sulfate, also known as 3-indoxyl sulfate, is a member of 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. Indoxyl sulfate is a metabolite of the common amino acid tryptophan and is derived through the consumption, digestion and microbial processing of protein-rich foods. Indoxyl sulfate is technically a bacterial co-metabolite, meaning that it is derived from both bacterial and host metabolism. Specifically, it is generated from dietary L-tryptophan which is converted to indole in the large intestine via tryptophanase-expressing gastrointestinal bacteria (PMID: 27102537 ). The resulting indole is converted to indoxyl in the liver via enzyme-mediated hydroxylation by the CYP450 enzyme CYP2E1 (PMID 11808865 ). Subsequently, indoxyl is converted into indoxyl sulfate by the SULT1A1 sulfotransferase enzyme in the liver (PMID: 12064372 ). Indoxyl sulfate has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ) and is classified as a protein-bound uremic solute. Indoxyl sulfate is known to bind to serum albumin (PMID: 22626821 ), to be transported by the OAT1 transporter (PMID: 34678967 ) and to be an agonist for the arylhydrocarbon receptor (AhR) (PMID: 32527975 ). High concentrations of indoxyl sulfate in whole blood or blood plasma are known to be associated with the development and progression of chronic kidney disease (CKD) as well as the development of cardiovascular disease (CVD) in humans and other mammals (PMID: 28754616 ). As a uremic toxin, indoxyl sulfate is known to stimulate glomerular sclerosis (PMID: 8035108 ), interstitial fibrosis (PMID: 33138205 ) and increase the rate of progression of renal failure. Indoxyl sulfate is a known tubular toxin (i.e., a renal tubule toxin) and directly induces apoptotic and necrotic cell death of tubular cells in the kidney (PMID: 33138205 ). Indoxyl sulfate upregulates signal transducers and activators of transcription 3 phosphorylation leading to increases in TGF-β1, monocyte chemotactic protein-1 and alpha-smooth muscle actin production, all of which participate in interstitial inflammation, renal fibrosis and, consequently, CKD progression (PMID: 33138205 ). Indoxyl sulfate is also a known cardiotoxin (PMID: 30200452 ). In plasma, indoxyl sulfate induces endothelial dysfunction by inhibiting endothelial proliferation and migration as well as disrupting wound repair in vitro (PMID: 14717914 ). Indoxyl sulfate is known to impair angiogenesis by suppressing endothelial cell tube formation and endothelial cell proliferation via chronic aryl hydrocarbon receptor (AhR) activation. Many studies suggest that indoxyl sulfate increases oxidative stress which further exacerbates endothelial dysfunction (PMID: 20876676 ). This ultimately leads to atherosclerosis, peripheral artery disease and cardiovascular disease, which are common in patients with CKD (PMID: 33456671 ). In hemodialyzed patients, serum levels of indoxyl sulfate are associated with levels of pentosidine, a marker of carbonyl and oxidative stress (PMID: 14524578 ). In vitro, indoxyl sulfate increases reactive oxygen species (ROS) production in tubular cells and increases NAD(P)H oxidase activity in endothelial cells (PMID: 29976888 ). Indoxyl sulfate also strongly decreases the levels of glutathione, one of the most active antioxidant systems of the cell (PMID: 29474405 ). In addition to its well-known renal toxicity and cardiotoxicity, indoxyl sulfate appears to have osteotoxic, myotoxic and neurotoxic effects. As an osteotoxin, indoxyl sulfate impairs osteoblast function and induces abnormalities of bone turnover (PMID: 28781957 ). Indoxyl sulfate appears to induce low-turnover bone disease by directly acting on both osteoblasts and osteoclast precursors to suppress bone formation and bone resorption. In vitro studies with mouse osteoblasts have shown that indoxyl sulfate suppresses the gene expression of osterix, osteocalcin, and bone morphogenetic protein 2 (BMP2), thereby inhibiting the formation of mineralized bone nodules, leading to suppressed bone formation (PMID: 28781957 ). As a myotoxin, indoxyl sulfate appears to induce sarcopenia, which is especially common in patients with CKD. In particular, indoxyl sulfate increases the production of several factors related to skeletal muscle breakdown, including reactive oxygen species (ROS) and inflammatory cytokines (TNF-α, IL-6 and TGF-β1) (PMID: 27549031 ). It also enhances the production of muscle atrophy-related genes, myostatin and atrogin-1 (PMID: 27549031 ). As a neurotoxin, indoxyl sulfate appears to disrupt the blood brain barrier. In particular, indoxyl sulfate binds to the aryl hydrocarbon receptor (AhR), which is widely expressed in the central nervous system. The binding of indoxyl sulfate to the AhR leads to blood-brain barrier disruption, which is associated with cognitive impairment in animal models of CKD (PMID: 32527975 ). Indoxyl sulfate, along with quinolinic acid and kynurenine, are significantly elevated in blood/plasma of individuals with dementia (PMID: 34493657 ). Recently, indoxyl sulfate has been shown to be associated with altered neural processing (as shown by functional MRI) and the serum abundance of indoxyl sulfate is positively correlated with severity of psychic anxiety in humans (PMID: 34697401 ).

Structure

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

HMDB00682.mol
  Mrv1652305271900162D          

 14 15  0  0  0  0            999 V2000
   -1.3492    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    1.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643    0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492    0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    1.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370   -1.1372    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -1.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -1.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000001

> <DATABASE_NAME>
MIME

> <SMILES>
OS(=O)(=O)OC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C8H7NO4S

> <MOLECULAR_WEIGHT>
213.21

> <EXACT_MASS>
213.009578407

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
19.370777626783628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1H-indol-3-yl)oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
1.2931291409999999

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.813693057567004

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8154557521719683

> <JCHEM_POLAR_SURFACE_AREA>
79.39

> <JCHEM_REFRACTIVITY>
49.117200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfooxy-1H-indole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB00682.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.519   2.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.519   0.898   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.185   0.128   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.149   0.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.149   2.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.185   3.208   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.613   0.422   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.519   1.668   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.617   2.910   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.088  -1.037   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       1.002  -2.123   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0       2.088  -3.208   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.083  -3.208   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.083  -1.037   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

Synonyms

Value	Source
3-Indolyl hydrogen sulfate	ChEBI
3-Indolyl sulfate	ChEBI
3-Indoxyl sulfate	ChEBI
3-Indoxylsulfuric acid	ChEBI
Indican	ChEBI
indol-3-yl Hydrogen sulfate	ChEBI
indol-3-yl Sulfate	ChEBI
indol-3-yl Sulphate	ChEBI
Indoxyl sulfic acid	ChEBI
Indoxyl sulphate	ChEBI
Indoxyl-3-sulphate	ChEBI
Indoxylsulfuric acid	ChEBI
3-Indolyl hydrogen sulfuric acid	Generator
3-Indolyl hydrogen sulphate	Generator
3-Indolyl hydrogen sulphuric acid	Generator
3-Indolyl sulfuric acid	Generator
3-Indolyl sulphate	Generator
3-Indolyl sulphuric acid	Generator
3-Indoxyl sulfuric acid	Generator
3-Indoxyl sulphate	Generator
3-Indoxyl sulphuric acid	Generator
3-Indoxylsulfate	Generator
3-Indoxylsulphate	Generator
3-Indoxylsulphuric acid	Generator
indol-3-yl Hydrogen sulfuric acid	Generator
indol-3-yl Hydrogen sulphate	Generator
indol-3-yl Hydrogen sulphuric acid	Generator
indol-3-yl Sulfuric acid	Generator
indol-3-yl Sulphuric acid	Generator
Indoxyl sulfuric acid	Generator
Indoxyl sulphuric acid	Generator
Indoxyl-3-sulfate	Generator
Indoxyl-3-sulfuric acid	Generator
Indoxyl-3-sulphuric acid	Generator
Indoxylsulfate	Generator
Indoxylsulphate	Generator
Indoxylsulphuric acid	Generator
1H-indol-3-yl Hydrogen sulfate	HMDB
1H-indol-3-yl Hydrogen sulphate	HMDB
indol-3-Ol	HMDB
Indican monosodium salt	HMDB
Monopotassium salt, indican	HMDB
Monosodium salt, indican	HMDB
Sulfate, indoxyl	HMDB
Indican monopotassium salt	HMDB
1H-indol-3-Ol hydrogen sulfate ester	HMDB
3-Sulphooxy-1H-indole	HMDB
Indoxyl sulfate	Generator

Molecular Formula

C₈H₇NO₄S

Average Mass

213.21

Monoisotopic Mass

213.009578407

IUPAC Name

(1H-indol-3-yl)oxidanesulfonic acid

Traditional Name

3-sulfooxy-1H-indole

CAS Registry Number

487-94-5

SMILES

OS(=O)(=O)OC1=CNC2=CC=CC=C12

InChI Identifier

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

Chemical 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

Substituents

Arylsulfate
Indole
Indole or derivatives
Substituted pyrrole
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Benzenoid
Pyrrole
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:43355 )
aryl sulfate (CHEBI:43355 )

Functional Ontology

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis (PMID: 17334708 , PMID: 32966057 , PMID: 22623390 , +128

Source	Link
Pubmed	PMID: 17334708
Pubmed	PMID: 32966057
Pubmed	PMID: 22623390
Pubmed	PMID: 16870009
Pubmed	PMID: 26910390
Pubmed	PMID: 8087979
Pubmed	PMID: 25105552
Pubmed	PMID: 17349089
Pubmed	PMID: 24023812
Pubmed	PMID: 12376931
Pubmed	PMID: 15992788
Pubmed	PMID: 24341803
Pubmed	PMID: 19468821
Pubmed	PMID: 9625050
Pubmed	PMID: 2420598
Pubmed	PMID: 27012787
Pubmed	PMID: 30830347
Pubmed	PMID: 19551947
Pubmed	PMID: 19309105
Pubmed	PMID: 2026685
Pubmed	PMID: 5727921
Pubmed	PMID: 22024767
Pubmed	PMID: 17031479
Pubmed	PMID: 9439441
Pubmed	PMID: 9625050
Pubmed	PMID: 28649521
Pubmed	PMID: 28649521
Pubmed	PMID: 12097436
Pubmed	PMID: 8257730
Pubmed	PMID: 3168222
Pubmed	PMID: 9869364
Pubmed	PMID: 3436096
Pubmed	PMID: 22157537
Pubmed	PMID: 1246461
Pubmed	PMID: 25691415
Pubmed	PMID: 18004736
Pubmed	PMID: 31506554
Pubmed	PMID: 20423563
Pubmed	PMID: 25536744
Pubmed	PMID: 21388201
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 14967154
Pubmed	PMID: 6774165
Pubmed	PMID: 21389975
Pubmed	PMID: 3709568
Pubmed	PMID: 8311084
Pubmed	PMID: 2242313
Pubmed	PMID: 20549362
Pubmed	PMID: 12555941
Pubmed	PMID: 10731506
Pubmed	PMID: 28157703
Pubmed	PMID: 20576202
Pubmed	PMID: 12368406
Pubmed	PMID: 26066683
Pubmed	PMID: 16736096
Pubmed	PMID: 25597510
Pubmed	PMID: 22800120
Pubmed	PMID: 16139832
Pubmed	PMID: 17287286
Pubmed	PMID: 17301081
Pubmed	PMID: 30817767
Pubmed	PMID: 25851806
Pubmed	PMID: 2587127
Pubmed	PMID: 11893004
Pubmed	PMID: 10102904
Pubmed	PMID: 23430553
Pubmed	PMID: 12705346
Pubmed	PMID: 19075476
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 31963255
Pubmed	PMID: 23093139
Pubmed	PMID: 22284503
Pubmed	PMID: 8503438
Pubmed	PMID: 1246461
Pubmed	PMID: 20502474
Pubmed	PMID: 15558695
Pubmed	PMID: 422265
Pubmed	PMID: 22308371
Pubmed	PMID: 20549362
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 28157703
Pubmed	PMID: 8487492
Pubmed	PMID: 23890588
Pubmed	PMID: 14586528
Pubmed	PMID: 12927681
Pubmed	PMID: 9686366
Pubmed	PMID: 9029640
Pubmed	PMID: 22148915
Pubmed	PMID: 27123458
Pubmed	PMID: 20971021
Pubmed	PMID: 3169394
Pubmed	PMID: 21670092
Pubmed	PMID: 23363473
Pubmed	PMID: 15519880
Pubmed	PMID: 2380628
Pubmed	PMID: 6616873
Pubmed	PMID: 1870421
Pubmed	PMID: 19754154
Pubmed	PMID: 9857238
Pubmed	PMID: 12771321
Pubmed	PMID: 2702744
Pubmed	PMID: 9554495
Pubmed	PMID: 19033659
Pubmed	PMID: 19033659
Pubmed	PMID: 22887155
Pubmed	PMID: 17474139
Pubmed	PMID: 18953024
Pubmed	PMID: 6774165
Pubmed	PMID: 11052553
Pubmed	PMID: 16939360
Pubmed	PMID: 22827565
Pubmed	PMID: 21736852
Pubmed	PMID: 12661026
Pubmed	PMID: 18818040
Pubmed	PMID: 23770102
Pubmed	PMID: 15651030
Pubmed	PMID: 11307586
Pubmed	PMID: 21389975
Pubmed	PMID: 1640293
Pubmed	PMID: 25712379
Pubmed	PMID: 23770102
Pubmed	PMID: 24390407
Pubmed	PMID: 26709303
Pubmed	PMID: 3354621
Pubmed	PMID: 29030856
Pubmed	PMID: 12706375
Pubmed	PMID: 9869358

)

Disposition

Biological location

Cellular substructure

Cytoplasm

Non-excretory biofluid

Blood

Excreta

Feces
Urine

Organ

Tissue

Muscle tissue

Skeletal muscle

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	1.29	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.12 m³·mol⁻¹	ChemAxon
Polarizability	19.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0fk9-1890000000-1ccefb12c0ecb58cd51f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0bu0-1940000000-990f3edaa0f09b455534	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0790000000-bc45c54af242dc72b9db	2014-06-16	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-1920000000-61513ebc6b785c807016	2017-08-28	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, Negative (Annotated)	splash10-03di-2090000000-53c9050daddd26dc4b7f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001i-9200000000-2fa7a5fde4214df01ed2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-001i-9000000000-c9eec4c054ae464098ed	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0090000000-3cb045bd6bc8f7f8c2b0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03e9-6290000000-83be1b2526f53131a6eb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-9400000000-13c9487183bfd123ac3b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-9100000000-cf4b2fd59d8e983cb538	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001i-9000000000-d0f51465d6c4ede36ea4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-01si-9350000000-7227b62421572ea4e5f7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0090000000-8fc92d1f6e32863121d3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03e9-6290000000-b9b7292552ce2dcfccff	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9400000000-7348f8347e517b6e1de2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9100000000-e9a190cf92fcef264150	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-d0f51465d6c4ede36ea4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-01si-9350000000-7227b62421572ea4e5f7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0900000000-d5c9e813f433f6a44f0f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-2ada8a129d47cf18cf2f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-8190000000-b7fa2468dad04ce9cf7b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0059-9300000000-4ef26d7f6ffd8a0309a8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0290000000-bcbb5c8a331119233939	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0910000000-0d28f0b8a4ef10141bf2	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2900000000-a394015845114b618d01	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0190000000-6917b03dbdcafea36737	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0930000000-6cb7fcdb7b15b9a9e80a	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-4900000000-3b57e4454fb97f3e1a1a	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular space

Biospecimen Locations

Blood
Bone Marrow
Brain
Cerebrospinal Fluid (CSF)
Endothelial tissue
Feces
Heart
Kidney
Liver
Skeletal Muscle
Urine

Tissue Locations

Bone Marrow
Brain
Endothelial tissue
Heart
Kidney
Liver
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Metabolism and Physiological Effects of Indoxyl Sulfate

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012719	Indoxyl	Indoxyl sulfate	sulfotransferase family, cytosolic, 1A, phenol-preferring, member 1	Indoxyl Sulfate Formation from Indoxyl	VMH; RHEA; KEGG	11808865

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

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia	Increased	Association	Human Blood	HMDB	22626821
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Mild cognitive impairment		Association	Human serum	PubMed	26797588
Uremic toxin		Association	Human Blood	PubMed	33138205
Anxiolytic		Association	Human Blood	PubMed	33138205
Depressant		Association	Human Blood	PubMed	33138205
Mild cognitive impairment		Association	Human Blood	PubMed	33138205
Promotes kidney damage		Association	Human Blood	PubMed	33138205
Promotes heart damage		Association	Human Blood	PubMed	33138205
Liver damage		Association	Human Blood	PubMed	33138205
Promotes nerve/brain damage		Association	Human Blood	PubMed	33138205
Atherogenic		Association	Human Blood	PubMed	33138205
Pro-inflammatory		Cell culture	renal tubular cells	PubMed	22610984
Aryl hydrocarbon receptor	agonist	Cell culture	House mouse CaCo-2 intestinal cells	PubMed	24563545
Aryl hydrocarbon receptor	agonist	Cell culture	astrocyte cells	PubMed	28659803
Neurotoxin		Animal_model	brain tissue	PubMed	28659803
Nuclear factor-κb	agonist	Cell culture	astrocyte cells	PubMed	28659803
Pro-inflammatory		Animal_model	brain tissue	PubMed	28659803
Ros production	induces	Cell culture	astrocyte cells	PubMed	28659803
Ros production	induces		Human endothelial cells	PubMed	28754616
Ros production	induces	Cell culture	renal tubular cells	PubMed	29474405
Aryl hydrocarbon receptor	agonist	Cell culture	astrocyte cells	PubMed	30336612
Nuclear factor-κb	agonist	Cell culture	astrocyte cells	PubMed	30336612
Pro-inflammatory		Cell culture	astrocyte cells	PubMed	30336612

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Food, diet (tryptophan-containing foods)		PubMed	31437929
Food	Food, diet (tryptophan-containing foods)		PubMed	31437929
Food	Food, diet (tryptophan-containing foods)		PubMed	31437929
Food	Food, diet (tryptophan-containing foods)		PubMed	31437929
Food	Food, diet (tryptophan-containing foods)		PubMed	31437929
Food	Dairy Products		FooDB	31437929
Food	Grains		FooDB	31437929
Food	Nuts and Legumes	Soy	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	>0.658				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	6321058
Human Blood	Detected and Quantified	21.11	12.2			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	2.49	1.36			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Urine	Detected and Quantified	22.4		6	64.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Blood	Detected and Quantified	3.8	2.2			uM	Adult (>18 years old)	Both	Parkinson's disease with motor fluctuation	HMDB	31726035
Human Blood	Detected and Quantified	3.8	3.0017			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Blood	Detected and Quantified	3.8	2.67			uM	Adult (>18 years old)	Both	Parkinson's disease without motor fluctuation	HMDB	31726035
Human Blood	Detected and Quantified	3.8	2.44			uM	Adult (>18 years old)	Both	Parkinson's disease	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.051	0.028			uM	Adult (>18 years old)	Both	Parkinson's disease with motor fluctuation	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.04	0.038			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.035	0.007			uM	Adult (>18 years old)	Both	Parkinson's disease without motor fluctuation	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.043	0.013			uM	Adult (>18 years old)	Both	Parkinson's disease	HMDB	31726035
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected and Quantified	14	4.2			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	18.98				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Urine	Detected and Quantified	36.932	21.826			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	41.689	44.971			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			1.41	51.64	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Urine	Detected and Quantified	129		45	191	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	17.76	6.58			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	19.74	5.26			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	420	210			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	21.11	12.20			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Urine	Detected and Quantified	>0.658				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	6321058
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.040	0.038			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Blood	Detected and Quantified	2.49	1.36			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Urine	Detected and Quantified	22.4		6.0	64.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	3.80	3.0017			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Urine	Detected and Quantified	36.932	21.826			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	41.689	44.971			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			1.41	51.64	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Urine	Detected and Quantified	129.0		45.0	191.0	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	14.0	4.2			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	17.76	6.58			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	19.74	5.26			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	420	210			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	18.98				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Bone marrow	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Endothelial tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Heart	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000682

DrugBank ID

DB07992

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022179

KNApSAcK ID

C00052323

Chemspider ID

9840

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indoxyl sulfate

METLIN ID

524

PubChem Compound

10258

PDB ID

Not Available

ChEBI ID

43355

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. doi: 10.1016/0731-7085(93)80171-v. [PubMed:8257730 ]
Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 ]
Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. doi: 10.1053/j.arrt.2003.08.002. [PubMed:14681860 ]
Iwasaki Y: [Uremic toxins and bone metabolism]. Clin Calcium. 2007 May;17(5):734-9. doi: CliCa0705734739. [PubMed:17471003 ]
Dou L, Jourde-Chiche N, Faure V, Cerini C, Berland Y, Dignat-George F, Brunet P: The uremic solute indoxyl sulfate induces oxidative stress in endothelial cells. J Thromb Haemost. 2007 Jun;5(6):1302-8. doi: 10.1111/j.1538-7836.2007.02540.x. [PubMed:17403109 ]
Evenepoel P, Meijers BK, Bammens BR, Verbeke K: Uremic toxins originating from colonic microbial metabolism. Kidney Int Suppl. 2009 Dec;(114):S12-9. doi: 10.1038/ki.2009.402. [PubMed:19946322 ]
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Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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Banoglu E, Jha GG, King RS: Hepatic microsomal metabolism of indole to indoxyl, a precursor of indoxyl sulfate. Eur J Drug Metab Pharmacokinet. 2001 Oct-Dec;26(4):235-40. doi: 10.1007/BF03226377. [PubMed:11808865 ]
Banoglu E, King RS: Sulfation of indoxyl by human and rat aryl (phenol) sulfotransferases to form indoxyl sulfate. Eur J Drug Metab Pharmacokinet. 2002 Apr-Jun;27(2):135-40. doi: 10.1007/BF03190428. [PubMed:12064372 ]
King J, Mihaila SM, Ahmed S, Truckenmuller R, Giselbrecht S, Masereeuw R, Carlier A: The Influence of OAT1 Density and Functionality on Indoxyl Sulfate Transport in the Human Proximal Tubule: An Integrated Computational and In Vitro Study. Toxins (Basel). 2021 Sep 22;13(10). pii: toxins13100674. doi: 10.3390/toxins13100674. [PubMed:34678967 ]
Bobot M, Thomas L, Moyon A, Fernandez S, McKay N, Balasse L, Garrigue P, Brige P, Chopinet S, Poitevin S, Cerini C, Brunet P, Dignat-George F, Burtey S, Guillet B, Hache G: Uremic Toxic Blood-Brain Barrier Disruption Mediated by AhR Activation Leads to Cognitive Impairment during Experimental Renal Dysfunction. J Am Soc Nephrol. 2020 Jul;31(7):1509-1521. doi: 10.1681/ASN.2019070728. Epub 2020 Jun 11. [PubMed:32527975 ]
Gao H, Liu S: Role of uremic toxin indoxyl sulfate in the progression of cardiovascular disease. Life Sci. 2017 Sep 15;185:23-29. doi: 10.1016/j.lfs.2017.07.027. Epub 2017 Jul 25. [PubMed:28754616 ]
Niwa T, Ise M: Indoxyl sulfate, a circulating uremic toxin, stimulates the progression of glomerular sclerosis. J Lab Clin Med. 1994 Jul;124(1):96-104. [PubMed:8035108 ]
Cheng TH, Ma MC, Liao MT, Zheng CM, Lu KC, Liao CH, Hou YC, Liu WC, Lu CL: Indoxyl Sulfate, a Tubular Toxin, Contributes to the Development of Chronic Kidney Disease. Toxins (Basel). 2020 Oct 29;12(11). pii: toxins12110684. doi: 10.3390/toxins12110684. [PubMed:33138205 ]
Lekawanvijit S: Cardiotoxicity of Uremic Toxins: A Driver of Cardiorenal Syndrome. Toxins (Basel). 2018 Sep 1;10(9). pii: toxins10090352. doi: 10.3390/toxins10090352. [PubMed:30200452 ]
Dou L, Bertrand E, Cerini C, Faure V, Sampol J, Vanholder R, Berland Y, Brunet P: The uremic solutes p-cresol and indoxyl sulfate inhibit endothelial proliferation and wound repair. Kidney Int. 2004 Feb;65(2):442-51. doi: 10.1111/j.1523-1755.2004.00399.x. [PubMed:14717914 ]
Yu M, Kim YJ, Kang DH: Indoxyl sulfate-induced endothelial dysfunction in patients with chronic kidney disease via an induction of oxidative stress. Clin J Am Soc Nephrol. 2011 Jan;6(1):30-9. doi: 10.2215/CJN.05340610. Epub 2010 Sep 28. [PubMed:20876676 ]
Kwiatkowska I, Hermanowicz JM, Mysliwiec M, Pawlak D: Oxidative Storm Induced by Tryptophan Metabolites: Missing Link between Atherosclerosis and Chronic Kidney Disease. Oxid Med Cell Longev. 2020 Dec 29;2020:6656033. doi: 10.1155/2020/6656033. eCollection 2020. [PubMed:33456671 ]
Kato A, Odamaki M, Hishida A: Association between blood indoxyl sulfate and carbonyl stress marker in hemodialysis patients. Clin Nephrol. 2003 Sep;60(3):161-7. doi: 10.5414/cnp60161. [PubMed:14524578 ]
Dias GF, Bonan NB, Steiner TM, Tozoni SS, Rodrigues S, Nakao LS, Kuntsevich V, Pecoits Filho R, Kotanko P, Moreno-Amaral AN: Indoxyl Sulfate, a Uremic Toxin, Stimulates Reactive Oxygen Species Production and Erythrocyte Cell Death Supposedly by an Organic Anion Transporter 2 (OAT2) and NADPH Oxidase Activity-Dependent Pathways. Toxins (Basel). 2018 Jul 5;10(7). pii: toxins10070280. doi: 10.3390/toxins10070280. [PubMed:29976888 ]
Edamatsu T, Fujieda A, Itoh Y: Phenyl sulfate, indoxyl sulfate and p-cresyl sulfate decrease glutathione level to render cells vulnerable to oxidative stress in renal tubular cells. PLoS One. 2018 Feb 23;13(2):e0193342. doi: 10.1371/journal.pone.0193342. eCollection 2018. [PubMed:29474405 ]
Watanabe K, Tominari T, Hirata M, Matsumoto C, Hirata J, Murphy G, Nagase H, Miyaura C, Inada M: Indoxyl sulfate, a uremic toxin in chronic kidney disease, suppresses both bone formation and bone resorption. FEBS Open Bio. 2017 Jul 20;7(8):1178-1185. doi: 10.1002/2211-5463.12258. eCollection 2017 Aug. [PubMed:28781957 ]
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Showing metabocard for Indoxyl sulfate (MMDBc0000001)

MOL for #<Metabolite:0x00007f46e08d5f08>

3D MOL for #<Metabolite:0x00007f46e08d5f08>

3D SDF for #<Metabolite:0x00007f46e08d5f08>

3D-SDF for #<Metabolite:0x00007f46e08d5f08>

PDB for #<Metabolite:0x00007f46e08d5f08>

3D PDB for #<Metabolite:0x00007f46e08d5f08>

SMILES for #<Metabolite:0x00007f46e08d5f08>

INCHI for #<Metabolite:0x00007f46e08d5f08>

Structure for #<Metabolite:0x00007f46e08d5f08>

3D Structure for #<Metabolite:0x00007f46e08d5f08>