CHEBI:66552 - largamide G

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ChEBI Name largamide G
ChEBI ID CHEBI:66552
Definition A 19-membered cyclodepsipeptide isolated from the marine cyanobacterium Oscillatoria sp. It exhibits significant inhibitory activity against the enzyme chymotrypsin (EC 3.4.21.1).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C60H82BrN9O18
Net Charge 0
Average Mass 1297.24700
Monoisotopic Mass 1295.496
InChI InChI=1S/C60H82BrN9O18/c1-29(2)47(66-51(78)31(5)62-52(79)40(63-55(82)45(76)28-71)11-9-10-34-12-18-37(73)19-13-34)56(83)68-49-33(7)88-60(87)48(30(3)4)67-54(81)43(27-36-17-24-44(75)39(61)26-36)69(8)59(86)50(32(6)72)70-46(77)25-23-42(58(70)85)65-53(80)41(64-57(49)84)22-16-35-14-20-38(74)21-15-35/h12-15,17-21,24,26,29-33,40-43,45-50,71-77H,9-11,16,22-23,25,27-28H2,1-8H3,(H,62,79)(H,63,82)(H,64,84)(H,65,80)(H,66,78)(H,67,81)(H,68,83)/t31-,32-,33+,40-,41-,42-,43-,45+,46+,47-,48-,49-,50-/m0/s1
InChIKey TUWXFKMBPYEGHC-BYVKOCPSSA-N
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](CCc1ccc(O)cc1)C(=O)N2
Metabolite of Species Details
Oscillatoria sp. (NCBI:txid1159) 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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing largamide G (CHEBI:66552) has functional parent D-glyceric acid (CHEBI:32398)
largamide G (CHEBI:66552) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
largamide G (CHEBI:66552) has role metabolite (CHEBI:25212)
largamide G (CHEBI:66552) is a cyclodepsipeptide (CHEBI:35213)
largamide G (CHEBI:66552) is a macrocycle (CHEBI:51026)
largamide G (CHEBI:66552) 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-(4-hydroxyphenyl)ethyl]-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 Number Type Source
10643043 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16930043 PubMed citation Europe PMC
Last Modified
17 October 2012