5,5',6,6'-tetrahydroxy-3,3'-biindolyl (CHEBI:174128)

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ChEBI Name	5,5',6,6'-tetrahydroxy-3,3'-biindolyl

ChEBI ID	CHEBI:174128

Definition	A hydroxyindole that is 1H-indole-5,6-diol substituted by a 5,6-dihydroxy-1H-indol-3-yl group at position 3.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	MetaboLights

Supplier Information

Download	Molfile XML SDF

Formula

C16H12N2O4

Net Charge

Average Mass

296.282

Monoisotopic Mass

296.07971

InChI

InChI=1S/C16H12N2O4/c19-13-1-7-9(5-17-11(7)3-15(13)21)10-6-18-12-4-16(22)14(20)2-8(10)12/h1-6,17-22H

InChIKey

UHYVKNUCMCSKMR-UHFFFAOYSA-N

SMILES

OC1=C(O)C=C2C(NC=C2C2=CNC3=CC(O)=C(O)C=C23)=C1

Metabolite of Species	Details
Beta vulgaris (NCBI:txid161934)	Isolated from peel extract. See: PubMed

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

ChEBI Ontology
Outgoing	5,5',6,6'-tetrahydroxy-3,3'-biindolyl (CHEBI:174128) has role antioxidant (CHEBI:22586) 5,5',6,6'-tetrahydroxy-3,3'-biindolyl (CHEBI:174128) has role plant metabolite (CHEBI:76924) 5,5',6,6'-tetrahydroxy-3,3'-biindolyl (CHEBI:174128) is a biindole alkaloid (CHEBI:167888) 5,5',6,6'-tetrahydroxy-3,3'-biindolyl (CHEBI:174128) is a hydroxyindoles (CHEBI:84729) 5,5',6,6'-tetrahydroxy-3,3'-biindolyl (CHEBI:174128) is a tetrol (CHEBI:33573)

IUPAC Name

1H,1'H-[3,3'-biindole]-5,5',6,6'-tetrol

Synonyms	Sources
3,3'-bi-1H-indole-5,5',6,6'-tetrol	KNApSAcK
3-(5,6-dihydroxy-1H-indol-3-yl)-1H-indole-5,6-diol	SUBMITTER
5,5',6,6'-tetrahydroxy-3,3'-bi-1H-indole	ChEBI
[3,3'-bi-1H-indole]-5,5',6,6'-tetrol	ChEBI

Registry Number	Type	Source
390401-91-9	CAS Registry Number	ChEBI

Citation	Type	Source
11724374	PubMed citation	Europe PMC

Last Modified

30 July 2021

General Comments
2021-07-29	Relevant articles: https://doi.org/10.1016/j.tet.2004.02.043
2021-07-29	Please note that there are clear spectroscopic differences between the natural product and that of the synthesised compound. Therefore it remains unclear whether or not the natural product is 5,5',6,6'-tetrahydroxy-3,3'-biindolyl.