CHEBI:66590 - longicalycinin A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name longicalycinin A
ChEBI ID CHEBI:66590
Definition A homodetic cyclic peptide composed of glycyl, L-phenylalanyl, L-tyrosyl, L-prolyl and L-phenylalanyl residues joined sequentially to give a 15-membered macrocycle. Isolated from Dianthus superbus var longicalycinus, it exhibits anti-cancer activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C34H37N5O6
Net Charge 0
Average Mass 611.689
Monoisotopic Mass 611.27438
InChI InChI=1S/C34H37N5O6/c40-25-15-13-24(14-16-25)20-28-34(45)39-17-7-12-29(39)33(44)37-26(18-22-8-3-1-4-9-22)31(42)35-21-30(41)36-27(32(43)38-28)19-23-10-5-2-6-11-23/h1-6,8-11,13-16,26-29,40H,7,12,17-21H2,(H,35,42)(H,36,41)(H,37,44)(H,38,43)/t26-,27-,28-,29-/m0/s1
InChIKey CWNYOXLYNGDTSL-DZUOILHNSA-N
SMILES N1C([C@@H](NC([C@]2(N(CCC2)C(=O)[C@@H](NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)C1)CC4=CC=C(C=C4)O)[H])=O)CC5=CC=CC=C5)=O
Metabolite of Species Details
Dianthus superbus var. longicalycinus (NCBI:txid713924) Found in whole plant (BTO:0001461). 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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing longicalycinin A (CHEBI:66590) has role antineoplastic agent (CHEBI:35610)
longicalycinin A (CHEBI:66590) has role metabolite (CHEBI:25212)
longicalycinin A (CHEBI:66590) is a homodetic cyclic peptide (CHEBI:24613)
longicalycinin A (CHEBI:66590) is a macrocycle (CHEBI:51026)
IUPAC Name
cyclo(glycyl-L-phenylalanyl-L-tyrosyl-L-prolyl-L-phenylalanyl)
Registry Number Type Source
10138036 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15744111 PubMed citation Europe PMC
17604256 PubMed citation Europe PMC
Last Modified
06 August 2016