herquline B (CHEBI:66012)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	herquline B

ChEBI ID	CHEBI:66012

Definition	An alkaloid comprising of a piperazine and cyclohexenone ring systems. Isolated from Penicillium herquei, it exhibits inhibitory activity against platelet aggregation.

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

Supplier Information

Download	Molfile XML SDF

Formula

C19H26N2O2

Net Charge

Average Mass

314.429

Monoisotopic Mass

314.19943

InChI

InChI=1S/C19H26N2O2/c1-21-11-14-6-12-2-4-18(22)16(8-12)17-9-13(3-5-19(17)23)7-15(21)10-20-14/h8-9,14-17,20H,2-7,10-11H2,1H3/t14-,15-,16-,17-/m0/s1

InChIKey

IKEHAWAEPHQJSM-QAETUUGQSA-N

SMILES

[H][C@]12CN(C)[C@]([H])(CN1)CC1=C[C@]([H])(C(=O)CC1)[C@]1([H])C=C(CCC1=O)C2

Metabolite of Species	Details
Penicillium herquei (NCBI:txid69774)	of strain Fg-372 See: PubMed
Penicillium herquei (NCBI:txid69774)	of strain FG 37 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):	Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium. 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):	platelet aggregation inhibitor A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

ChEBI Ontology
Outgoing	herquline B (CHEBI:66012) has role Penicillium metabolite (CHEBI:76964) herquline B (CHEBI:66012) has role platelet aggregation inhibitor (CHEBI:50427) herquline B (CHEBI:66012) is a alkaloid (CHEBI:22315) herquline B (CHEBI:66012) is a cyclic ketone (CHEBI:3992) herquline B (CHEBI:66012) is a organic heterotetracyclic compound (CHEBI:38163) herquline B (CHEBI:66012) is a secondary amino compound (CHEBI:50995) herquline B (CHEBI:66012) is a tertiary amino compound (CHEBI:50996) herquline B (CHEBI:66012) is conjugate base of herquline B(1+) (CHEBI:146143)

Incoming	herquline B(1+) (CHEBI:146143) is conjugate acid of herquline B (CHEBI:66012)

Synonyms	Sources
(−)-herquline B	ChEBI
(1S,7S,8S,14S)-15-methyl-15,17-diazatetracyclo[12.2.2.1^3,7.1^8,12]icosa-3(20),12(19)-diene-6,9-dione	IUPAC

Last Modified

07 March 2024

General Comment
2024-03-07	Structure is based on evidence found in scheme 4 (PMID:30561198).