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CHEBI:65583 - dragomabin

Default Structure
ChEBI IDCHEBI:65583
ChEBI Namedragomabin
Stars
DefinitionA lipopeptide consisting of a 2-methyloct-7-ynoyl moiety attached to a linear tetrapeptide comprising of N-methyl-L-phenylalanyl, L-alanyl, N-methyl-L-alanyl and Nα,O-dimethyl-L-tyrosine units. It is isolated from a Panamanian strain of the marine cyanobacterium Lyngbya majuscula and displays antimalarial activity.
Last Modified6 December 2012
DownloadsMolfile
FormulaC37H51N5O6
Net Charge0
Average Mass661.844
Monoisotopic Mass661.38393
SMILESC#CCCCC[C@H](C)C(=O)N(C)[C@@H](Cc1ccccc1)C(=O)N[C@@H](C)C(=O)N(C)[C@@H](C)C(=O)N(C)[C@@H](Cc1ccc(OC)cc1)C(N)=O
InChIInChI=1S/C37H51N5O6/c1-9-10-11-13-16-25(2)35(45)42(7)32(24-28-17-14-12-15-18-28)34(44)39-26(3)36(46)40(5)27(4)37(47)41(6)31(33(38)43)23-29-19-21-30(48-8)22-20-29/h1,12,14-15,17-22,25-27,31-32H,10-11,13,16,23-24H2,2-8H3,(H2,38,43)(H,39,44)/t25-,26-,27-,31-,32-/m0/s1
InChIKeyJAYHQHZOWYDLDQ-PONGSQKHSA-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)
dragomabin (CHEBI:65583) has role antimalarial (CHEBI:38068)
dragomabin (CHEBI:65583) has role metabolite (CHEBI:25212)
dragomabin (CHEBI:65583) is a lipopeptide (CHEBI:46895)
IUPAC Name 
N-methyl-N-[(2S)-2-methyloct-7-ynoyl]-L-phenylalanyl-L-alanyl-N-methyl-L-alanyl-Nα,O-dimethyl-L-tyrosinamide
Registry NumbersSources
Reaxys:11195402Reaxys
Citations