CHEBI:64531 - fumitremorgin B

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name fumitremorgin B
ChEBI ID CHEBI:64531
Definition An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi via a tryptophan-proline diketopiperazine intermediate.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C27H33N3O5
Net Charge 0
Average Mass 479.56800
Monoisotopic Mass 479.24202
InChI InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3/t19-,21-,24-,27+/m0/s1
InChIKey WEIYXEFMCIRZHC-MWGWWEMPSA-N
SMILES [H][C@@]12CCCN1C(=O)[C@]1(O)[C@@H](O)c3c(n(CC=C(C)C)c4cc(OC)ccc34)[C@]([H])(C=C(C)C)N1C2=O
Roles Classification
Biological Role(s): 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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fumitremorgin B (CHEBI:64531) has role mycotoxin (CHEBI:25442)
fumitremorgin B (CHEBI:64531) is a indole alkaloid (CHEBI:38958)
fumitremorgin B (CHEBI:64531) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name
(5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione
Synonyms Sources
fumitremorgin B UniProt
Lanosulin ChemIDplus
Registry Numbers Types Sources
12626-17-4 CAS Registry Number ChemIDplus
905336 Reaxys Registry Number Reaxys
Citations Types Sources
10095931 PubMed citation Europe PMC
1155935 PubMed citation Europe PMC
16345234 PubMed citation Europe PMC
18683158 PubMed citation Europe PMC
19373974 PubMed citation Europe PMC
19763315 PubMed citation Europe PMC
22409377 PubMed citation Europe PMC
2881766 PubMed citation Europe PMC
6626168 PubMed citation Europe PMC
8698634 PubMed citation Europe PMC
8721621 PubMed citation Europe PMC
9388887 PubMed citation Europe PMC
Last Modified
25 March 2013