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3-Indolyl-beta-D-glucuronide

HCID 2733785
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Grundinformationen

CAS
35804-66-1
Standard-SMILES
O=C(O)[C@H]1O[C@@H](Oc2c[nH]c3ccccc23)[C@H](O)[C@@H](O)[C@@H]1O
InChIKey
KUYNOZVWCFXSNE-BYNIDDHOSA-N
Summenformel
C14H15NO7
Durchschnittliche Molmasse
309,27 g/mol
Monoisotopische Masse
309,08485182

Überblick

Inodxyl glucuronide is a glucosiduronic acid.

Namen und Bezeichner

Bevorzugter Name
3-Indolyl-beta-D-glucuronide
IUPAC
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indol-3-yloxy)oxane-2-carboxylic acid
Englischer Name
3-Indoxyl-beta-D-glucuronic acid cyclohexylammonium salt
Summenformel
C14H15NO7
Molmasse
309.27

Namen und Synonyme

Indoxyl glucuronide35804-66-1Indoxyl-beta-D-glucuronide3-Indolyl-beta-D-glucuronideDTXSID20957188RefChem:911436DTXCID8013851323-Indoxyl-beta-D-glucuronic acid cyclohexylammonium salt3-Indolyl-|A-D-glucuronide(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indol-3-yloxy)oxane-2-carboxylic acidbeta-D-Glucopyranosiduronic acid, 1H-indol-3-ylIndoxyl-beta-d-glucuronide cyclohexylammonium salt
Weitere Namen anzeigen
IBDGY-beta-D-GlcUA.CHXY-β-D-GlcA · CHXY(TM)-BETA-D-GLCA CHX3-Indolyl-β-D-glucuronideMonocyclohexylammoniumsaltIBDG CYCLOHEXYLAMMONIUM SALTIndoxyl-beta-D-glucuronicacid3-Indoxyl-beta-D-glucuronicacid
Inodxyl glucuronideIndoxyl-Glucuronide3-Indolyl--D-glucuronide1H-Indol-3-yl beta-D-glucopyranosiduronic acidSCHEMBL155476INDOXYL-BETA-GLUCURONIDEorb2567234orb3141428

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,1
Polarare Oberfläche (TPSA)
132 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
3
Schwere Atome
22
Formalladung
0
Komplexität
420

Experimentelle und physikochemische Eigenschaften

Physical DescriptionSolid

Physikochemische Eigenschaften

Siedepunkt
669 · 669.0±55.0 °C(Predicted)
Dichte
1.693 · 1.693±0.06 g/cm3(Predicted)
storage temp.
20 °C · −20°C
pka
2.82 · 2.82±0.70(Predicted)
Aggregatzustand
powder
InChI
1S/C14H15NO7/c16-9-10(17)12(13(19)20)22-14(11(9)18)21-8-5-15-7-4-2-1-3-6(7)8/h1-5,9-12,14-18H,(H,19,20)
InChIKey
KUYNOZVWCFXSNE-UHFFFAOYSA-N
SMILES
OC1C(OC(C(O)C1O)C(O)=O)Oc2c[nH]c3ccccc23

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

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 Eintrag

Uremic toxins such as indoxyl-beta-D-glucuronide 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 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

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

Verwendung und Herstellung

UsesNaturally produced by the body (endogenous).

Anbieter57 Anbieter

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Datenbank-Bezeichner

CAS
35804-66-1
PubChem CID
2733785
DTXSID
DTXSID20957188
ChEMBL
CHEMBL2074589
ChEBI
CHEBI:145223
Nikkaji
J486.490E
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
3
hs_code
29349990
risk_code
36/37/38
hazard_code
Xi
safety_code
24/25-36-26
Speicherklasse
11 - Combustible Solids
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