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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:57 UTC

HMDB ID

HMDB0000682

Secondary Accession Numbers

HMDB0003309
HMDB00682
HMDB03309

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>
HMDB0000682

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₈H₇NO₄S

Average Molecular Weight

213.21

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)
Coma (HMDB: HMDB0000682)

Central nervous system disorder

Psychiatric disorder

Psychosis (HMDB: HMDB0000682)

Neurotic, stress-related, or somatoform disorder

Anxiety (PMID: 34697401)

Mood disorder

Major depressive disorder (PMID: 34697401)

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0000682)
Uremia (HMDB: HMDB0000682)
Chronic kidney disease (HMDB: HMDB0000682)

Observation

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0000682)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 22626821)
Cerebrospinal Fluid (CSF) (PMID: 31726035)

Tissue substructure

Muscle (HMDB: HMDB0000682)

Organ

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0000682)

Connective tissue

Bone marrow (HMDB: HMDB0000682)

Endothelial tissue (HMDB: HMDB0000682)

Excreta

Biofluid or Excreta

Urine (PMID: 6321058)
Feces (PMID: 27543620)

Cellular substructure

Route of exposure

Parenteral

Dermal (HMDB: HMDB0000682)

Enteral

Ingestion (HMDB: HMDB0000682)

Source

Exogenous

Exogenous (HMDB: HMDB0000682)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Nut

Nuts (HMDB: HMDB0000682)

Milk and milk product

Dairy products (HMDB: HMDB0000682)

Egg

Eggs (HMDB: HMDB0000682)

Soy

Soy (HMDB: HMDB0000682)

Meats (HMDB: HMDB0000682)
Legumes (HMDB: HMDB0000682)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000682)

Endogenous

Endogenous (HMDB: HMDB0000682)

Microbe

Microbe (HMDB: HMDB0000682)
Escherichia coli (HMDB: HMDB0000682)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000682)

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000217)

Biological role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	140.596	30932474
[M-H]-	Not Available	140.596	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000024

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.633	31661259
DarkChem	[M-H]-	143.48	31661259
AllCCS	[M+H]+	145.43	32859911
AllCCS	[M-H]-	139.037	32859911
DeepCCS	[M-2H]-	168.274	30932474
DeepCCS	[M+Na]+	142.969	30932474
AllCCS	[M+H]+	145.4	32859911
AllCCS	[M+H-H2O]+	141.2	32859911
AllCCS	[M+NH4]+	149.3	32859911
AllCCS	[M+Na]+	150.5	32859911
AllCCS	[M-H]-	139.0	32859911
AllCCS	[M+Na-2H]-	139.2	32859911
AllCCS	[M+HCOO]-	139.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indoxyl sulfate	OS(=O)(=O)OC1=CNC2=CC=CC=C12	3458.1	Standard polar	33892256
Indoxyl sulfate	OS(=O)(=O)OC1=CNC2=CC=CC=C12	1830.9	Standard non polar	33892256
Indoxyl sulfate	OS(=O)(=O)OC1=CNC2=CC=CC=C12	2203.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indoxyl sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=C[NH]C2=CC=CC=C12	1999.5	Semi standard non polar	33892256
Indoxyl sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=C[NH]C2=CC=CC=C12	1946.5	Standard non polar	33892256
Indoxyl sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=C[NH]C2=CC=CC=C12	2919.9	Standard polar	33892256
Indoxyl sulfate,1TMS,isomer #2	C[Si](C)(C)N1C=C(OS(=O)(=O)O)C2=CC=CC=C21	2048.1	Semi standard non polar	33892256
Indoxyl sulfate,1TMS,isomer #2	C[Si](C)(C)N1C=C(OS(=O)(=O)O)C2=CC=CC=C21	2068.3	Standard non polar	33892256
Indoxyl sulfate,1TMS,isomer #2	C[Si](C)(C)N1C=C(OS(=O)(=O)O)C2=CC=CC=C21	2960.1	Standard polar	33892256
Indoxyl sulfate,2TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CN([Si](C)(C)C)C2=CC=CC=C12	2096.6	Semi standard non polar	33892256
Indoxyl sulfate,2TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CN([Si](C)(C)C)C2=CC=CC=C12	2130.4	Standard non polar	33892256
Indoxyl sulfate,2TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CN([Si](C)(C)C)C2=CC=CC=C12	2653.9	Standard polar	33892256
Indoxyl sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=C[NH]C2=CC=CC=C12	2283.9	Semi standard non polar	33892256
Indoxyl sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=C[NH]C2=CC=CC=C12	2199.5	Standard non polar	33892256
Indoxyl sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=C[NH]C2=CC=CC=C12	2945.2	Standard polar	33892256
Indoxyl sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(OS(=O)(=O)O)C2=CC=CC=C21	2320.7	Semi standard non polar	33892256
Indoxyl sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(OS(=O)(=O)O)C2=CC=CC=C21	2274.7	Standard non polar	33892256
Indoxyl sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(OS(=O)(=O)O)C2=CC=CC=C21	3011.9	Standard polar	33892256
Indoxyl sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2519.6	Semi standard non polar	33892256
Indoxyl sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2609.3	Standard non polar	33892256
Indoxyl sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2763.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Indoxyl sulfate GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0fk9-1890000000-1ccefb12c0ecb58cd51f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Indoxyl sulfate GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0bu0-1940000000-990f3edaa0f09b455534	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Indoxyl sulfate GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0790000000-bc45c54af242dc72b9db	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoxyl sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-1920000000-61513ebc6b785c807016	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoxyl sulfate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-03di-2090000000-53c9050daddd26dc4b7f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-001i-9200000000-2fa7a5fde4214df01ed2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-001i-9000000000-c9eec4c054ae464098ed	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-03di-0090000000-3cb045bd6bc8f7f8c2b0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-03e9-6290000000-83be1b2526f53131a6eb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-001i-9400000000-13c9487183bfd123ac3b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-001i-9100000000-cf4b2fd59d8e983cb538	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-001i-9000000000-d0f51465d6c4ede36ea4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-01si-9350000000-7227b62421572ea4e5f7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ , negative-QTOF	splash10-03di-0090000000-8fc92d1f6e32863121d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ , negative-QTOF	splash10-03e9-6290000000-b9b7292552ce2dcfccff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ , negative-QTOF	splash10-001i-9400000000-7348f8347e517b6e1de2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ , negative-QTOF	splash10-001i-9100000000-e9a190cf92fcef264150	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QQ , negative-QTOF	splash10-001i-9000000000-d0f51465d6c4ede36ea4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate LC-ESI-QTOF , negative-QTOF	splash10-01si-9350000000-7227b62421572ea4e5f7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate , positive-QTOF	splash10-001i-0900000000-d5c9e813f433f6a44f0f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate 40V, Negative-QTOF	splash10-004i-9000000000-2ada8a129d47cf18cf2f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate 10V, Negative-QTOF	splash10-03e9-8190000000-b7fa2468dad04ce9cf7b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoxyl sulfate 20V, Negative-QTOF	splash10-0059-9300000000-4ef26d7f6ffd8a0309a8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoxyl sulfate 10V, Positive-QTOF	splash10-03di-0290000000-bcbb5c8a331119233939	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoxyl sulfate 20V, Positive-QTOF	splash10-0159-0910000000-0d28f0b8a4ef10141bf2	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoxyl sulfate 40V, Positive-QTOF	splash10-014i-2900000000-a394015845114b618d01	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoxyl sulfate 10V, Negative-QTOF	splash10-03di-0190000000-6917b03dbdcafea36737	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoxyl sulfate 20V, Negative-QTOF	splash10-001i-0930000000-6cb7fcdb7b15b9a9e80a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoxyl sulfate 40V, Negative-QTOF	splash10-001i-4900000000-3b57e4454fb97f3e1a1a	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular space

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Bone Marrow
Brain
Endothelial tissue
Heart
Kidney
Liver
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.80 +/- 3.0017 uM	Adult (>18 years old)	Both	Normal	31726035	details
Blood	Detected and Quantified	14.0 +/- 4.2 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	2.49 +/- 1.36 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.040 +/- 0.038 uM	Adult (>18 years old)	Both	Normal	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	129.0 (45.0-191.0) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	19.74 +/- 5.26 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	17.76 +/- 6.58 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	1.41-51.64 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	41.689 +/- 44.971 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	18.98 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected and Quantified	>0.658 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	6321058	details
Urine	Detected and Quantified	22.4 (6.0-64.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.57 (1.67-4.03) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	420 +/- 210 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.80 +/- 2.44 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Blood	Detected and Quantified	21.11 +/- 12.20 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected and Quantified	3.80 +/- 2.20 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Blood	Detected and Quantified	3.80 +/- 2.67 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.043 +/- 0.013 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.051 +/- 0.028 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.035 +/- 0.0070 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	36.932 +/- 21.826 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Uremia
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

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

VMH ID

Not Available

MarkerDB ID

MDB00000217

Good Scents ID

Not Available

References

Synthesis Reference

Robertson, Alexander. Synthesis of glucosides. I. Synthesis of indican. Journal of the Chemical Society (1927), 1937-43.

Material Safety Data Sheet (MSDS)

Download (PDF)

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. [PubMed:8257730 ]
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 ]
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 ]
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. [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. [PubMed:14681860 ]
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 ]
Iwasaki Y: [Uremic toxins and bone metabolism]. Clin Calcium. 2007 May;17(5):734-9. [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. [PubMed:17403109 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Zhang LS, Davies SS: Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions. Genome Med. 2016 Apr 21;8(1):46. doi: 10.1186/s13073-016-0296-x. [PubMed:27102537 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Enoki Y, Watanabe H, Arake R, Sugimoto R, Imafuku T, Tominaga Y, Ishima Y, Kotani S, Nakajima M, Tanaka M, Matsushita K, Fukagawa M, Otagiri M, Maruyama T: Indoxyl sulfate potentiates skeletal muscle atrophy by inducing the oxidative stress-mediated expression of myostatin and atrogin-1. Sci Rep. 2016 Aug 23;6:32084. doi: 10.1038/srep32084. [PubMed:27549031 ]
Teruya T, Chen YJ, Kondoh H, Fukuji Y, Yanagida M: Whole-blood metabolomics of dementia patients reveal classes of disease-linked metabolites. Proc Natl Acad Sci U S A. 2021 Sep 14;118(37). pii: 2022857118. doi: 10.1073/pnas.2022857118. [PubMed:34493657 ]
Brydges CR, Fiehn O, Mayberg HS, Schreiber H, Dehkordi SM, Bhattacharyya S, Cha J, Choi KS, Craighead WE, Krishnan RR, Rush AJ, Dunlop BW, Kaddurah-Daouk R: Indoxyl sulfate, a gut microbiome-derived uremic toxin, is associated with psychic anxiety and its functional magnetic resonance imaging-based neurologic signature. Sci Rep. 2021 Oct 25;11(1):21011. doi: 10.1038/s41598-021-99845-1. [PubMed:34697401 ]

Enzymes

Enzyme Details

1. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Showing metabocard for Indoxyl sulfate (HMDB0000682)

MOL for HMDB0000682 (Indoxyl sulfate)

3D MOL for HMDB0000682 (Indoxyl sulfate)

3D SDF for HMDB0000682 (Indoxyl sulfate)

3D-SDF for HMDB0000682 (Indoxyl sulfate)

PDB for HMDB0000682 (Indoxyl sulfate)

3D PDB for HMDB0000682 (Indoxyl sulfate)

SMILES for HMDB0000682 (Indoxyl sulfate)

INCHI for HMDB0000682 (Indoxyl sulfate)

Structure for HMDB0000682 (Indoxyl sulfate)

3D Structure for HMDB0000682 (Indoxyl sulfate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes