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CHEBI:66551 - largamide F

ChEBI IDCHEBI:66551
ChEBI Namelargamide F
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
FormulaC60H82BrN9O17
Net Charge0
Average Mass1281.266
Monoisotopic Mass1279.50120
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](Cc1ccc(C)cc1)C(=O)N2
InChIInChI=1S/C60H82BrN9O17/c1-29(2)47(66-51(77)32(6)62-52(78)40(63-55(81)45(75)28-71)12-10-11-35-17-20-38(73)21-18-35)56(82)68-49-34(8)87-60(86)48(30(3)4)67-54(80)43(27-37-19-23-44(74)39(61)25-37)69(9)59(85)50(33(7)72)70-46(76)24-22-41(58(70)84)64-53(79)42(65-57(49)83)26-36-15-13-31(5)14-16-36/h13-21,23,25,29-30,32-34,40-43,45-50,71-76H,10-12,22,24,26-28H2,1-9H3,(H,62,78)(H,63,81)(H,64,79)(H,65,83)(H,66,77)(H,67,80)(H,68,82)/t32-,33-,34+,40-,41-,42-,43-,45+,46+,47-,48-,49-,50-/m0/s1
InChIKeyRHQKNCSUWKVICI-JLENUOFPSA-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:
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).
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 F (CHEBI:66551) has functional parent D-glyceric acid (CHEBI:32398)
largamide F (CHEBI:66551) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
largamide F (CHEBI:66551) has role metabolite (CHEBI:25212)
largamide F (CHEBI:66551) is a cyclodepsipeptide (CHEBI:35213)
largamide F (CHEBI:66551) is a macrocycle (CHEBI:51026)
largamide F (CHEBI:66551) 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-(4-methylbenzyl)-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:10642969Reaxys
Citations