Structure via PubChem · Public domain (PubChem)
indirubin
Sign in to saveIndirubin is a chemical compound most often produced as a byproduct of bacterial metabolism. For instance, it is one of the compounds responsible for the generally benign condition purple urine bag syndrome, resulting from bacteria metabolizing indoxyl sulfate found naturally in urine.
Chemical data
- Formula
- C16H10N2O2
- Molecular weight
- 262.26 g/mol
- IUPAC name
- (3E)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one
- SMILES
- C1=CC=C2C(=C1)/C(=C\3/C(=O)C4=CC=CC=C4N3)/C(=O)N2
- InChIKey
- CRDNMYFJWFXOCH-BUHFOSPRSA-N
- XLogP
- 2.3
- Polar surface area
- 58.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
870 papers- Indirubin Inhibits LPS-Induced Inflammation via TLR4 Abrogation Mediated by the NF-kB and MAPK Signaling Pathways.Inflammation · 2017
- Pharmacological properties of indirubin and its derivatives.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2022
- Macrophage-Mediated Transport of Insoluble Indirubin Induces Hepatic Injury During Intestinal Inflammation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
- Indirubin induces tolerogenic dendritic cells via aryl hydrocarbon receptor activation and ameliorates allergic asthma in a murine model by expanding Foxp3-expressing regulatory T cells.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Indirubin and meisoindigo in the treatment of chronic myelogenous leukemia in China.Leukemia & lymphoma · 2002
via PubMed
Wikidata facts
- Subclass of
- indole alkaloid
- Mass
- 262.074
- Has use
- dye
Show 5 more facts
- chemical formula
- C₁₆H₁₀N₂O₂
- found in taxon
- Couroupita guianensis
- canonical SMILES
- C1=CC=C2C(=C1)C(=C3C(=O)C4=CC=CC=C4N3)C(=O)N2
- isomeric SMILES
- C1=CC=C2C(=C1)/C(=C\3/C(=O)C4=CC=CC=C4N3)/C(=O)N2
- Commons category
- Indirubin
Sources (3)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Indigo naturalis
- Research
- See also
- References
Indirubin is a chemical compound most often produced as a byproduct of bacterial metabolism. For instance, it is one of the compounds responsible for the generally benign condition purple urine bag syndrome, resulting from bacteria metabolizing indoxyl sulfate found naturally in urine.
Indirubin is a structural isomer (more precisely is position isomer) of indigo dye.
Excerpted from Wikipedia’s “indirubin” article, available under the CC BY-SA 4.0 licence.