MiMeDB: Showing metabocard for Indoxyl sulfate (MMDBc0000001)

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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

Functional Ontology

Physical Properties

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

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

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

References

General References

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Showing metabocard for Indoxyl sulfate (MMDBc0000001)

MOL for #<Metabolite:0x00007f53b9903198>

3D MOL for #<Metabolite:0x00007f53b9903198>

3D SDF for #<Metabolite:0x00007f53b9903198>

3D-SDF for #<Metabolite:0x00007f53b9903198>

PDB for #<Metabolite:0x00007f53b9903198>

3D PDB for #<Metabolite:0x00007f53b9903198>

SMILES for #<Metabolite:0x00007f53b9903198>

INCHI for #<Metabolite:0x00007f53b9903198>

Structure for #<Metabolite:0x00007f53b9903198>

3D Structure for #<Metabolite:0x00007f53b9903198>