Violacein

ChEBI: A member of the class of hydroxyindoles resulting from the formal oxidative coupling between the 3-position of 1,3-dihydro-2H-indol-2-one and the 3-position of 1,3-dihydro-2H-pyrrol-2-one, which is substituted at the 5 position by a 5-hydroxy-1H-indol-3-yl group, where the newly-formed double bond has E configuration. It is a purple chromobacterial pigment that has antibacterial, antifungal, antiprotozoan, and anticancer properties.

Violacein is a member of the class of hydroxyindoles resulting from the formal oxidative coupling between the 3-position of 1,3-dihydro-2H-indol-2-one and the 3-position of 1,3-dihydro-2H-pyrrol-2-one, which is substituted at the 5 position by a 5-hydroxy-1H-indol-3-yl group, where the newly-formed double bond has E configuration. It is a purple chromobacterial pigment that has antibacterial, antifungal, antiprotozoan, and anticancer properties. It has a role as a bacterial metabolite, an antineoplastic agent, an apoptosis inducer, an antibacterial agent and an antifungal agent. It is a member of hydroxyindoles, a member of pyrroles, a member of oxindoles and an olefinic compound. It derives from a proviolacein.

Violacein is an intense violet pigment formed by the condensation of two tryptophan units, found in a number of bacteria, notably Chromobacterium violaceum. The regulation of pigment biosynthesis is the chromogenic basis for the use of C. violaceum CV26 for the detection of quorum sensing mediators. Violacein exhibits broad spectrum actvity against bacteria, protozoans (including malaria), viruses and mammalian cell lines. Violacein cell toxicity resembles TNF-α signal transduction.

Molecular Weight:343.3
XLogP3:2.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:343.09569129
Monoisotopic Mass:343.09569129
Topological Polar Surface Area:102
Heavy Atom Count:26
Complexity:753
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes