CHEBI:66461 - semicochliodinol A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name semicochliodinol A
ChEBI ID CHEBI:66461
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C27H22N2O4
Net Charge 0
Average Mass 438.47460
Monoisotopic Mass 438.15796
InChI InChI=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
InChIKey XNQAJERZSLDENY-UHFFFAOYSA-N
SMILES CC(C)=CCc1ccc2[nH]cc(C3=C(O)C(=O)C(=C(O)C3=O)c3c[nH]c4ccccc34)c2c1
Metabolite of Species Details
Chrysosporium merdarium (NCBI:txid108922) of strain P 5656 See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
HIV protease inhibitor
An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
epidermal growth factor receptor antagonist
An antagonist at the epidermal growth factor receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
Citation Waiting for Citations Type Source
9207909 PubMed citation Europe PMC
Last Modified
03 June 2016