CHEBI:72765 - verruculogen

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ChEBI Name verruculogen
ChEBI ID CHEBI:72765
Definition An organic heterohexacyclic compound that is a mycotoxic indole alkaloid isolated from Penicillium and Aspergillus species.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KAX
Supplier Information
Download Molfile XML SDF
Formula C27H33N3O7
Net Charge 0
Average Mass 511.56680
Monoisotopic Mass 511.232
InChI InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1
InChIKey LRXYHMMJJCTUMY-GWXUGYLUSA-N
SMILES [H][C@@]12CCCN1C(=O)[C@]1(O)[C@@H](O)c3c4n([C@H](OOC(C)(C)C[C@]4([H])N1C2=O)C=C(C)C)c1cc(OC)ccc31
Roles Classification
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
potassium channel blocker
An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
mycotoxin
Poisonous substance produced by fungi.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing verruculogen (CHEBI:72765) has role Aspergillus metabolite (CHEBI:76956)
verruculogen (CHEBI:72765) has role Penicillium metabolite (CHEBI:76964)
verruculogen (CHEBI:72765) has role GABA modulator (CHEBI:50268)
verruculogen (CHEBI:72765) has role mycotoxin (CHEBI:25442)
verruculogen (CHEBI:72765) has role potassium channel blocker (CHEBI:50509)
verruculogen (CHEBI:72765) is a aromatic ether (CHEBI:35618)
verruculogen (CHEBI:72765) is a diol (CHEBI:23824)
verruculogen (CHEBI:72765) is a indole alkaloid (CHEBI:38958)
verruculogen (CHEBI:72765) is a organic heterohexacyclic compound (CHEBI:51914)
verruculogen (CHEBI:72765) is a organic peroxide (CHEBI:25702)
Incoming fumitremorgin A (CHEBI:72766) has functional parent verruculogen (CHEBI:72765)
IUPAC Name
(5R,10S,10aR,14aS,15bS)-10,10a-dihydroxy-6-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione
Synonyms Sources
TR 1 ChEBI
TR 1 toxin ChEBI
verruculogen UniProt
Manual Xref Database
C20045 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
12771-72-1 CAS Registry Number ChemIDplus
3579339 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16375825 PubMed citation Europe PMC
17244350 PubMed citation Europe PMC
18683158 PubMed citation SUBMITTER
19763315 PubMed citation SUBMITTER
22757643 PubMed citation Europe PMC
23109474 PubMed citation Europe PMC
3453096 PubMed citation Europe PMC
Last Modified
07 November 2013