fumisoquin A (CHEBI:167211)

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ChEBI Name	fumisoquin A

ChEBI ID	CHEBI:167211

Definition	A pyridoisoquinoline that is (11aR)-1,3,4,6,11,11a-hexahydro-2H-pyrido[1,2-b]isoquinoline substituted by hydoxy groups at positions 1S,7,8 and 11R, by an amino group at position 3S and an oxo group at position 4. It is produced by a biosynthetic gene cluster called fsq in the human pathogen Aspergillus fumigatus.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C13H16N2O5

Net Charge

Average Mass

280.280

Monoisotopic Mass

280.10592

InChI

InChI=1S/C13H16N2O5/c14-7-3-9(17)10-12(19)5-1-2-8(16)11(18)6(5)4-15(10)13(7)20/h1-2,7,9-10,12,16-19H,3-4,14H2/t7-,9-,10+,12+/m0/s1

InChIKey

DGLVASJKYCTLGR-QAHWYCSRSA-N

SMILES

[H][C@]12[C@@H](O)C[C@H](N)C(=O)N1CC1=C(C=CC(O)=C1O)[C@H]2O

Metabolite of Species	Details
Aspergillus fumigatus (NCBI:txid746128)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

ChEBI Ontology
Outgoing	fumisoquin A (CHEBI:167211) has role Aspergillus metabolite (CHEBI:76956) fumisoquin A (CHEBI:167211) is a isoquinoline alkaloid (CHEBI:24921) fumisoquin A (CHEBI:167211) is a phenols (CHEBI:33853) fumisoquin A (CHEBI:167211) is a primary amino compound (CHEBI:50994) fumisoquin A (CHEBI:167211) is a pyridoisoquinoline (CHEBI:61692) fumisoquin A (CHEBI:167211) is a tetrol (CHEBI:33573) fumisoquin A (CHEBI:167211) is conjugate base of fumisoquin A(1+) (CHEBI:167199)

Incoming	fumisoquin A(1+) (CHEBI:167199) is conjugate acid of fumisoquin A (CHEBI:167211)

IUPAC Name

(1S,3S,11R,11aR)-3-amino-1,7,8,11-tetrahydroxy-1,2,3,6,11,11a-hexahydro-4H-pyrido[1,2-b]isoquinolin-4-one

Synonym	Source
(1S,3S,11R,11aR)-3-amino-1,7,8,11-tetrahydroxy-1H,2H,3H,4H,6H,11H,11aH-pyrido[1,2-b]isoquinolin-4-one	IUPAC

Citation	Type	Source
27065235	PubMed citation	Europe PMC

Last Modified

21 January 2021