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CHEBI:65980 - grassypeptolide

ChEBI IDCHEBI:65980
ChEBI Namegrassypeptolide
Stars
DefinitionA 31-membered macrocyclic cyclodepsipeptide isolated from the cyanobacterium Lyngbya confervoides and has been shown to exhibit antineoplastic activity.
Last Modified8 February 2013
DownloadsMolfile
FormulaC56H79N9O10S2
Net Charge0
Average Mass1102.435
Monoisotopic Mass1101.53913
SMILES[H][C@]1([C@@H](C)O)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@]2([H])CSC(=N2)[C@@H](CC)NC(=O)[C@]2([H])CSC(=N2)[C@@H](Cc2ccccc2)N(C)C(=O)[C@]2([H])CCCN2C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](Cc2ccccc2)OC(=O)[C@H](C)[C@@H](C)NC1=O
InChIInChI=1S/C56H79N9O10S2/c1-12-38-50-60-40(30-76-50)52(70)62(9)42(26-31(2)3)48(68)61-45(35(8)66)49(69)57-34(7)33(6)56(74)75-44(28-37-22-17-14-18-23-37)54(72)64(11)46(32(4)5)55(73)65-25-19-24-41(65)53(71)63(10)43(27-36-20-15-13-16-21-36)51-59-39(29-77-51)47(67)58-38/h13-18,20-23,31-35,38-46,66H,12,19,24-30H2,1-11H3,(H,57,69)(H,58,67)(H,61,68)/t33-,34-,35-,38-,39+,40+,41+,42-,43-,44+,45-,46+/m1/s1
InChIKeyKUUZFDUZAFJFSJ-IHTUVIFUSA-N
Species of MetaboliteComponentSourceComments
Lyngbya confervoides (ncbitaxon:207921) - PubMed (18220404)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
grassypeptolide (CHEBI:65980) has role antineoplastic agent (CHEBI:35610)
grassypeptolide (CHEBI:65980) has role metabolite (CHEBI:25212)
grassypeptolide (CHEBI:65980) is a cyclodepsipeptide (CHEBI:35213)
grassypeptolide (CHEBI:65980) is a macrocycle (CHEBI:51026)
IUPAC Name 
(3R,7R,10R,14R,17R,20R,23R,24R,27S,30S,35aS)-3,27-dibenzyl-10-ethyl-20-[(1R)-1-hydroxyethyl]-2,16,23,24,29-pentamethyl-17-(2-methylpropyl)-30-(propan-2-yl)hexadecahydro-1H,6H,13H,27H-7,4:14,11-di(azeno)pyrrolo[1,2-g][1,13,20,4,7,10,17,24,27,30]oxadithiaheptaazacyclotritriacontine-1,8,15,18,21,25,28,31(7H,14H,22H)-octone
Manual XrefsDatabases
24600256ChemSpider
Registry NumbersSources
Reaxys:18860639Reaxys
Citations