CHEBI:156435 - isoflavipucine

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ChEBI Name isoflavipucine
ChEBI ID CHEBI:156435
Definition A natural product found in Aspergillus flavipes with weak cytotoxicity against human leukemia HL-60 cells.
Stars This entity has been manually annotated by a third party.
Submitter Martin Larralde
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C12H15NO4
Net Charge 0
Average Mass 237.255
Monoisotopic Mass 237.10011
InChI InChI=1S/C12H15NO4/c1-6(2)4-8(14)12-16-9-5-7(3)13-11(15)10(9)17-12/h5-6,12H,4H2,1-3H3,(H,13,15)
InChIKey VALUPXXLHSBISM-UHFFFAOYSA-N
SMILES C1(OC2=C(O1)C(=O)NC(C)=C2)C(=O)CC(C)C
Metabolite of Species Details
Phoma sp. (NCBI:txid1707701) See: PubMed
Calcarisporium arbuscula (NCBI:txid240499) of strain NRRL 3705 See: PubMed
Aspergillus terreus NIH2624 (NCBI:txid341663) See: PubMed
Aspergillus flavipes (NCBI:txid41900) See: DOI
Roles Classification
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
mycotoxin
Poisonous substance produced by fungi.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing isoflavipucine (CHEBI:156435) has part δ-lactam ring (CHEBI:52910)
isoflavipucine (CHEBI:156435) has part isobutyl group (CHEBI:30356)
isoflavipucine (CHEBI:156435) has role Aspergillus metabolite (CHEBI:76956)
isoflavipucine (CHEBI:156435) has role antineoplastic agent (CHEBI:35610)
isoflavipucine (CHEBI:156435) has role mycotoxin (CHEBI:25442)
isoflavipucine (CHEBI:156435) is a δ-lactam (CHEBI:77727)
isoflavipucine (CHEBI:156435) is a cyclic acetal (CHEBI:59770)
isoflavipucine (CHEBI:156435) is a dioxolane (CHEBI:39430)
isoflavipucine (CHEBI:156435) is a ketone (CHEBI:17087)
IUPAC Name
(2R)-6-methyl-2-(3-methylbutanoyl)-5H-[1,3]dioxolo[4,5-c]pyridin-4-one
Synonym Source
(±)-isoflavipucine SUBMITTER
Citations
Cheng JT, Cao F, Chen XA, Li YQ, Mao XM (2020)
Genomic and transcriptomic survey of an endophytic fungus Calcarisporium arbuscula NRRL 3705 and potential overview of its secondary metabolites.
BMC genomics 21, 424 (Source: SUBMITTER) [PubMed:32580753]
[show Abstract]
Mizutani S, Komori K, Taniguchi T, Monde K, Kuramochi K, Tsubaki K (2016)
A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine.
Angewandte Chemie (International ed. in English) 55, 9553-9556 (Source: SUBMITTER) [PubMed:27376480]
[show Abstract]
Gressler M, Zaehle C, Scherlach K, Hertweck C, Brock M (2011)
Multifactorial induction of an orphan PKS-NRPS gene cluster in Aspergillus terreus.
Chemistry & biology 18, 198-209 (Source: SUBMITTER) [PubMed:21236704]
[show Abstract]