Indoxyl Sulfate

HCID 10258CAS 1336-79-4

Basic information

Standard SMILES
O=S(=O)(O)Oc1c[nH]c2ccccc12
InChIKey
BXFFHSIDQOFMLE-UHFFFAOYSA-N
Molecular formula
C8H7NO4S
Average molar mass
213.21 g/mol
Monoisotopic mass
213.0095787

Overview

Indoxyl sulfate is an aryl sulfate that is indoxyl in which the hydroxyl hydrogen is substituted by a sulfo group. It has a role as a human metabolite. It is a member of indoles and an aryl sulfate. It is functionally related to an indoxyl. It is a conjugate acid of an indoxyl sulfate(1-).

Names & identifiers

Preferred name
Indoxyl Sulfate
IUPAC
1H-indol-3-yl hydrogen sulfate
English name
Indican
Molecular formula
C8H7NO4S
Molecular weight
213.21

Names & synonyms

Indoxyl sulfate1H-indol-3-yl hydrogen sulfate487-94-53-Indoxyl sulfateIndol-3-yl sulfateindoxyl sulphate3-indolyl sulfateindoxyl-3-sulphateIndoxyl sulfic acid3-indolyl hydrogen sulfateindol-3-yl sulphateindol-3-yl hydrogen sulfate
Show more names
1H-Indol-3-ylsulfateIndoxyl sulfate (Standard)Indican(metabolic indican)Sulfuric acid 1H-indole-3-yl ester1H-Indol-3-ol, 3-(hydrogen sulfate)Indican (metabolic indolyl sulfate)1H-Indol-3-ol, hydrogen sulfate (ester)Sulfuric acid hydrogen 1H-indol-3-yl ester
indol-3-ol1H-indol-3-yloxidanesulfonic acidKT0QA88913DTXSID701043787RefChem:1087381DTXCID00202087Indoxylsulfuric acid3-Indoxylsulfuric acid

Database identifiers

CAS
1336-79-4、487-94-5
PubChem CID
10258
DTXSID
DTXSID701043787
ChEMBL
CHEMBL1233636
ChEBI
CHEBI:43355
UNII
KT0QA88913
Nikkaji
J6.028C

Properties

Computed structural properties

XLogP
1.3
Topological polar surface area
87.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
14

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section · 3 items

140.6 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

143.3 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

143.4 Ų [M-H]-

Physicochemical properties

Density
1.666 · 1.666±0.06 g/cm3(Predicted)
pka
-3.63 · -3.63±0.18(Predicted)
FDA UNII
0 QA88913 · KT0QA88913

Safety & regulation

Toxicology

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 item

Uremic toxins such as Indoxyl sulfate are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

Signs and Symptoms · 1 item

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Tissue LocationsKidney
Cellular LocationsCytoplasm

Uses & manufacturing

UsesNaturally produced by the body (endogenous).

Upstream & downstream products

Upstream raw materials

Suppliers6 total

广州佳途科技股份有限公司81960175 18933936954 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]

Additional notes

DefinitionChEBI: An aryl sulfate that is indoxyl in which the hydroxyl hydrogen is substituted by a sulfo group.

Related reactions

0 records

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Linked notes

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