CHEBI:65980 - grassypeptolide

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ChEBI Name grassypeptolide
ChEBI ID CHEBI:65980
Definition A 31-membered macrocyclic cyclodepsipeptide isolated from the cyanobacterium Lyngbya confervoides and has been shown to exhibit antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C56H79N9O10S2
Net Charge 0
Average Mass 1102.41100
Monoisotopic Mass 1101.539
InChI InChI=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
InChIKey KUUZFDUZAFJFSJ-IHTUVIFUSA-N
SMILES [H][C@@]12CSC(=N1)[C@@H](Cc1ccccc1)N(C)C(=O)[C@]1([H])CCCN1C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](Cc1ccccc1)OC(=O)[C@H](C)[C@@H](C)NC(=O)[C@]([H])(NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@]1([H])CSC(=N1)[C@@H](CC)NC2=O)[C@@H](C)O
Metabolite of Species Details
Lyngbya confervoides (NCBI:txid207921) 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
Database Link Database
24600256 ChemSpider
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Registry Number Type Source
18860639 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18220404 PubMed citation Europe PMC
Last Modified
08 February 2013