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CHEBI:134347 - glandicoline B

ChEBI IDCHEBI:134347
ChEBI Nameglandicoline B
Stars
DefinitionAn indole alkaloid with a tetracyclic skeleton that is isolated from Penicillium chrysogenum.
Last Modified3 April 2017
SubmitterAnne Morgat
DownloadsMolfile
FormulaC22H21N5O4
Net Charge0
Average Mass419.441
Monoisotopic Mass419.15935
SMILESC=CC(C)(C)[C@]12C=C(O)C(=O)N3/C(=C/c4cncn4)C(=O)N[C@@]31N(O)c1ccccc12
InChIInChI=1S/C22H21N5O4/c1-4-20(2,3)21-10-17(28)19(30)26-16(9-13-11-23-12-24-13)18(29)25-22(21,26)27(31)15-8-6-5-7-14(15)21/h4-12,28,31H,1H2,2-3H3,(H,23,24)(H,25,29)/b16-9+/t21-,22-/m1/s1
InChIKeyYEVSOYBNHBOQJZ-GCTRCSCRSA-N
Species of MetaboliteComponentSourceComments
Penicillium chrysogenum (ncbitaxon:5076) - PubMed (22118684)
Penicillium sp. (ncbitaxon:5081) - Article (Quim. Nova, (2012) Vol. 35, 4, 771-774) Strain: PBR.2.2.2
Roles Classification
Biological Roles:
mycotoxin  Poisonous substance produced by fungi.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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)
glandicoline B (CHEBI:134347) has role antibacterial agent (CHEBI:33282)
glandicoline B (CHEBI:134347) has role mycotoxin (CHEBI:25442)
glandicoline B (CHEBI:134347) is a enol (CHEBI:33823)
glandicoline B (CHEBI:134347) is a imidazoles (CHEBI:24780)
glandicoline B (CHEBI:134347) is a indole alkaloid (CHEBI:38958)
glandicoline B (CHEBI:134347) is a lactam (CHEBI:24995)
glandicoline B (CHEBI:134347) is a olefinic compound (CHEBI:78840)
glandicoline B (CHEBI:134347) is a organic heterotetracyclic compound (CHEBI:38163)
Incoming Relation(s)
meleagrine (CHEBI:70399) has functional parent glandicoline B (CHEBI:134347)
IUPAC Name 
(3E,7aS,12aR)-6,12-dihydroxy-3-[(1H-imidazol-4-yl)methylidene]-7a-(2-methylbut-3-en-2-yl)-7a,12-dihydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione
UniProt Name  Source
glandicoline BUniProt
Manual XrefsDatabases
CPD-17390MetaCyc
Citations