CHEBI:65584 - dragonamide A

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ChEBI Name dragonamide A
ChEBI ID CHEBI:65584
Definition A lipopeptide consisting of a 2-methyloct-7-ynoyl moiety attached to a linear tetrapeptide comprising of N-methyl-L-phenylalanyl and N-methyl-L-valine units. It is isolated from a Panamanian strain of the marine cyanobacterium Lyngbya majuscula and displays antimalarial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C37H59N5O5
Net Charge 0
Average Mass 653.89490
Monoisotopic Mass 653.45162
InChI InChI=1S/C37H59N5O5/c1-13-14-15-17-20-27(8)34(44)40(10)31(25(4)5)36(46)42(12)32(26(6)7)37(47)41(11)30(24(2)3)35(45)39(9)29(33(38)43)23-28-21-18-16-19-22-28/h1,16,18-19,21-22,24-27,29-32H,14-15,17,20,23H2,2-12H3,(H2,38,43)/t27-,29-,30-,31-,32-/m0/s1
InChIKey LFBMRFDBJDFLTN-QDNWXXHKSA-N
SMILES CC(C)[C@H](N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@@H](C)CCCCC#C)C(=O)N(C)[C@@H](Cc1ccccc1)C(N)=O
Metabolite of Species Details
Lyngbya majuscula (NCBI:txid158786) Panamanian strain of the marine cyanobacterium 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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dragonamide A (CHEBI:65584) has role antimalarial (CHEBI:38068)
dragonamide A (CHEBI:65584) has role metabolite (CHEBI:25212)
dragonamide A (CHEBI:65584) is a lipopeptide (CHEBI:46895)
dragonamide A (CHEBI:65584) is a terminal acetylenic compound (CHEBI:73477)
IUPAC Name
N-methyl-N-[(2S)-2-methyloct-7-ynoyl]-L-valyl-N-methyl-L-valyl-N-methyl-L-valyl-Nα-methyl-L-phenylalaninamide
Registry Number Type Source
10226310 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17441769 PubMed citation Europe PMC
Last Modified
02 May 2013