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CHEBI:65584 - dragonamide A

ChEBI IDCHEBI:65584
ChEBI Namedragonamide A
Stars
DefinitionA 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.
Last Modified2 May 2013
DownloadsMolfile
FormulaC37H59N5O5
Net Charge0
Average Mass653.909
Monoisotopic Mass653.45162
SMILESC#CCCCC[C@H](C)C(=O)N(C)[C@H](C(=O)N(C)[C@H](C(=O)N(C)[C@H](C(=O)N(C)[C@@H](Cc1ccccc1)C(N)=O)C(C)C)C(C)C)C(C)C
InChIInChI=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
InChIKeyLFBMRFDBJDFLTN-QDNWXXHKSA-N
Species of MetaboliteComponentSourceComments
Lyngbya majuscula (ncbitaxon:158786) - PubMed (17441769) Panamanian strain of the marine cyanobacterium
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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:
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.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:10226310Reaxys
Citations