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CHEBI:66550 - largamide E

ChEBI IDCHEBI:66550
ChEBI Namelargamide E
Stars
DefinitionA 19-membered cyclodepsipeptide isolated from the marine cyanobacterium Oscillatoria sp. It exhibits significant inhibitory activity against the enzyme chymotrypsin (EC 3.4.21.1).
Last Modified17 October 2012
DownloadsMolfile
FormulaC56H82ClN9O17
Net Charge0
Average Mass1188.771
Monoisotopic Mass1187.55172
SMILES[H][C@]12CC[C@@H](O)N(C1=O)[C@@]([H])([C@H](C)O)C(=O)N(C)[C@@H](Cc1ccc(O)c(Cl)c1)C(=O)N[C@@H](C(C)C)C(=O)O[C@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCCc1ccc(O)cc1)NC(=O)[C@H](O)CO)C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N2
InChIInChI=1S/C56H82ClN9O17/c1-26(2)22-38-49(75)60-37-19-21-42(72)66(54(37)80)46(30(8)68)55(81)65(10)39(24-33-16-20-40(70)35(57)23-33)50(76)63-44(28(5)6)56(82)83-31(9)45(53(79)61-38)64-52(78)43(27(3)4)62-47(73)29(7)58-48(74)36(59-51(77)41(71)25-67)13-11-12-32-14-17-34(69)18-15-32/h14-18,20,23,26-31,36-39,41-46,67-72H,11-13,19,21-22,24-25H2,1-10H3,(H,58,74)(H,59,77)(H,60,75)(H,61,79)(H,62,73)(H,63,76)(H,64,78)/t29-,30-,31+,36-,37-,38-,39-,41+,42+,43-,44-,45-,46-/m0/s1
InChIKeyDDRDKAKGHUYAPS-NCLDEZEWSA-N
Species of MetaboliteComponentSourceComments
Oscillatoria sp. (ncbitaxon:1159) - PubMed (16930043)
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.
ChEBI Ontology
Outgoing Relation(s)
largamide E (CHEBI:66550) has functional parent D-glyceric acid (CHEBI:32398)
largamide E (CHEBI:66550) has role metabolite (CHEBI:25212)
largamide E (CHEBI:66550) is a cyclodepsipeptide (CHEBI:35213)
largamide E (CHEBI:66550) is a macrocycle (CHEBI:51026)
largamide E (CHEBI:66550) is a organochlorine compound (CHEBI:36683)
IUPAC Name 
N-[(2R)-2,3-dihydroxypropanoyl]-5-(4-hydroxyphenyl)-L-norvalyl-L-alanyl-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-5-(3-chloro-4-hydroxybenzyl)-21-hydroxy-2-[(1S)-1-hydroxyethyl]-4,11-dimethyl-15-(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docos-12-yl]-L-valinamide
Registry NumbersSources
Reaxys:10642521Reaxys
Citations