CHEBI:65849 - epichlicin

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ChEBI Name epichlicin
ChEBI ID CHEBI:65849
Definition A homodetic cyclic peptide containing L-Pro, D-Tyr, L-Ser, L-Asn and L-Gln as the amino acid residues. Isolated from an endophytic fungus, Epichloe typhina, it exhibits inhibitory activity toward the spore germination of Cladosporium phlei, a pathogenic fungus of the timothy plant.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C48H74N12O14
Net Charge 0
Average Mass 1043.17320
Monoisotopic Mass 1042.54475
InChI InChI=1S/C48H74N12O14/c1-2-3-4-5-6-7-8-9-10-12-28-22-41(67)54-32(23-38(50)64)44(70)56-31(21-27-14-16-29(62)17-15-27)43(69)57-33(24-39(51)65)45(71)55-30(18-19-37(49)63)42(68)59-35(26-61)46(72)58-34(25-40(52)66)48(74)60-20-11-13-36(60)47(73)53-28/h14-17,28,30-36,61-62H,2-13,18-26H2,1H3,(H2,49,63)(H2,50,64)(H2,51,65)(H2,52,66)(H,53,73)(H,54,67)(H,55,71)(H,56,70)(H,57,69)(H,58,72)(H,59,68)/t28-,30+,31-,32+,33+,34+,35+,36+/m1/s1
InChIKey QPLUQODTAQYAFC-FVBCJJOCSA-N
SMILES CCCCCCCCCCC[C@@H]1CC(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](Cc2ccc(O)cc2)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N2CCC[C@H]2C(=O)N1
Metabolite of Species Details
Epichloe typhina (NCBI:txid5113) Organism is an endophytic fungus of Phleum prantense 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): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing epichlicin (CHEBI:65849) has role antifungal agent (CHEBI:35718)
epichlicin (CHEBI:65849) has role fungal metabolite (CHEBI:76946)
epichlicin (CHEBI:65849) is a homodetic cyclic peptide (CHEBI:24613)
epichlicin (CHEBI:65849) is a macrocycle (CHEBI:51026)
IUPAC Name
3-[(3R,7S,10R,13S,16S,19S,22S,27aS)-7,13,22-tris(2-amino-2-oxoethyl)-10-(4-hydroxybenzyl)-19-(hydroxymethyl)-1,5,8,11,14,17,20,23-octaoxo-3-undecylhexacosahydro-1H-pyrrolo[2,1-c][1,4,7,10,13,16,19,22]octaazacyclopentacosin-16-yl]propanamide
Registry Number Type Source
11108273 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17587677 PubMed citation Europe PMC
Last Modified
06 July 2015