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CHEBI:65658 - cordyheptapeptide A

ChEBI IDCHEBI:65658
ChEBI Namecordyheptapeptide A
Stars
DefinitionA homodectic cyclic peptide made up from N-methylglycyl, L-phenylalanyl, N-methyl-L-tyrosyl, L-isoleucyl, L-leucyl, N-methyl-D-phenylalanyl and L-prolyl residues linked in sequence. It is an antimalarial drug isolated from the insect pathogenic fungus Cordyceps.
Last Modified6 August 2016
DownloadsMolfile
FormulaC49H65N7O8
Net Charge0
Average Mass880.100
Monoisotopic Mass879.48946
SMILES[H][C@@]12CCCN1C(=O)[C@@H](Cc1ccccc1)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@]([H])([C@@H](C)CC)NC(=O)[C@H](Cc1ccc(O)cc1)N(C)C(=O)[C@H](Cc1ccccc1)NC(=O)CN(C)C2=O
InChIInChI=1S/C49H65N7O8/c1-8-32(4)43-45(60)51-37(26-31(2)3)46(61)55(7)41(29-34-18-13-10-14-19-34)49(64)56-25-15-20-39(56)48(63)53(5)30-42(58)50-38(27-33-16-11-9-12-17-33)47(62)54(6)40(44(59)52-43)28-35-21-23-36(57)24-22-35/h9-14,16-19,21-24,31-32,37-41,43,57H,8,15,20,25-30H2,1-7H3,(H,50,58)(H,51,60)(H,52,59)/t32-,37-,38-,39-,40-,41+,43-/m0/s1
InChIKeyZXPWAGZHBVVLJM-PPLXTMPISA-N
Species of MetaboliteComponentSourceComments
Cordyceps (ncbitaxon:45234) - PubMed (16499340) Strain: BCC1788
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)
cordyheptapeptide A (CHEBI:65658) has role antimalarial (CHEBI:38068)
cordyheptapeptide A (CHEBI:65658) has role metabolite (CHEBI:25212)
cordyheptapeptide A (CHEBI:65658) is a homodetic cyclic peptide (CHEBI:24613)
cordyheptapeptide A (CHEBI:65658) is a macrocycle (CHEBI:51026)
cordyheptapeptide A (CHEBI:65658) is a phenols (CHEBI:33853)
IUPAC Name 
cyclo(N-methylglycyl-L-phenylalanyl-N-methyl-L-tyrosyl-L-isoleucyl-L-leucyl-N-methyl-D-phenylalanyl-L-prolyl)
Synonym  Source
(6S,9S,12S,15S,18R,23aS)-6,18-dibenzyl-12-[(2S)-butan-2-yl]-9-(4-hydroxybenzyl)-15-isobutyl-2,8,17-trimethylhexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13,16,19]heptaazacyclohenicosine-1,4,7,10,13,16,19-heptoneIUPAC
Registry NumbersSources
Reaxys:11237468Reaxys
Citations