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CHEBI:66547 - largamide D

Default Structure
ChEBI IDCHEBI:66547
ChEBI Namelargamide D
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
FormulaC56H82BrN9O17
Net Charge0
Average Mass1233.222
Monoisotopic Mass1231.50120
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(Br)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/C56H82BrN9O17/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
InChIKeyVIXXINFROOFGPE-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 Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.4.21.1 (chymotrypsin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of chymotrypsin (EC 3.4.21.1).
ChEBI Ontology
Outgoing Relation(s)
largamide D (CHEBI:66547) has functional parent D-glyceric acid (CHEBI:32398)
largamide D (CHEBI:66547) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
largamide D (CHEBI:66547) has role metabolite (CHEBI:25212)
largamide D (CHEBI:66547) is a cyclodepsipeptide (CHEBI:35213)
largamide D (CHEBI:66547) is a macrocycle (CHEBI:51026)
largamide D (CHEBI:66547) is a organobromine compound (CHEBI:37141)
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-bromo-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:10642559Reaxys
Citations