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CHEBI:66461 - semicochliodinol A

ChEBI IDCHEBI:66461
ChEBI Namesemicochliodinol A
Stars
DefinitionA bisindole alkaloid that is quinone bearing hydroxy substituents at positions 2 and 5 and two indol-3-yl groups at positions 3 and 6, one of which is carrying a prenyl group at position 5. Isolated from the culture broth of Chrysosporium merdarium, it acts as an inhibitor of HIV-1 protease and EGF-R protein tyrosine kinase.
Last Modified3 June 2016
DownloadsMolfile
FormulaC27H22N2O4
Net Charge0
Average Mass438.483
Monoisotopic Mass438.15796
SMILESCC(C)=CCc1ccc2ncc(C3=C(O)C(=O)C(c4cnc5ccccc45)=C(O)C3=O)c2c1
InChIInChI=1S/C27H22N2O4/c1-14(2)7-8-15-9-10-21-17(11-15)19(13-29-21)23-26(32)24(30)22(25(31)27(23)33)18-12-28-20-6-4-3-5-16(18)20/h3-7,9-13,28-30,33H,8H2,1-2H3
InChIKeyXNQAJERZSLDENY-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Chrysosporium merdarium (ncbitaxon:108922) - PubMed (9207909) Strain: P 5656
Roles Classification
Biological Roles:
epidermal growth factor receptor antagonist  An antagonist at the epidermal growth factor receptor.
HIV protease inhibitor  An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
semicochliodinol A (CHEBI:66461) has role epidermal growth factor receptor antagonist (CHEBI:74440)
semicochliodinol A (CHEBI:66461) has role HIV protease inhibitor (CHEBI:35660)
semicochliodinol A (CHEBI:66461) has role metabolite (CHEBI:25212)
semicochliodinol A (CHEBI:66461) is a bisindole alkaloid (CHEBI:51879)
semicochliodinol A (CHEBI:66461) is a dihydroxy-1,4-benzoquinones (CHEBI:132126)
semicochliodinol A (CHEBI:66461) is a enol (CHEBI:33823)
IUPAC Name 
2,5-dihydroxy-3-(1H-indol-3-yl)-6-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
Citations