Celogentin C
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Overview
Description
Celogentin C is a natural product found in Celosia argentea with data available.
Scientific Research Applications
Synthesis and Structural Insights
Celogentin C, a complex bicyclic octapeptide, was first isolated from the seeds of Celosia argentea. Its unique structure, featuring two cross-links between amino acid side chains, has been a focal point for synthetic efforts. Notably, the bond between the leucine β-carbon atom and the indole C6 of tryptophan forms one ring, while the other contains a C–N linkage between indole C2 and imidazole N1. This intricate structure has made this compound the subject of extensive synthetic studies, striving to replicate its potent antimitotic properties (Ma et al., 2009; Ma et al., 2010; He et al., 2006).
Antimicrobial Activity
Research has also focused on creating simplified mimics of this compound, which have shown moderate antibacterial activity. These studies suggest that the bicyclic structure of this compound, with its unique sidechain-sidechain crosslinks, may contribute to its biological activities, including potential inhibition of bacterial protomicrotubule formation (Thombare et al., 2017).
Tubulin Polymerization Inhibition
This compound and its derivatives have demonstrated significant inhibitory effects on tubulin polymerization, a key process in cell division. This potent activity, higher than related compounds like moroidin, has made this compound an important lead structure for antimitotic agents (Kobayashi et al., 2001).
Ribosomal Biosynthesis of Moroidin Peptides
Recent studies have delved into the ribosomal biosynthesis of moroidin-type bicyclic peptides, including this compound. Understanding the genetic and biosynthetic pathways of these peptides could pave the way for novel drug development strategies, potentially exploiting the cytotoxic effects of this compound against certain cancer cell lines (Kersten et al., 2022).
Properties
Molecular Formula |
C50H70N14O10 |
---|---|
Molecular Weight |
1027.2 g/mol |
IUPAC Name |
(7S,10S,13S,19S,22S,25S,28S,29R)-10-[3-(diaminomethylideneamino)propyl]-25-(2-methylpropyl)-9,12,18,21,24,27-hexaoxo-28-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]-22,29-di(propan-2-yl)-2,4,8,11,17,20,23,26,35-nonazahexacyclo[17.16.2.12,5.130,34.013,17.033,36]nonatriaconta-1(36),3,5(39),30(38),31,33-hexaene-7-carboxylic acid |
InChI |
InChI=1S/C50H70N14O10/c1-23(2)17-33-44(68)61-39(25(5)6)46(70)59-34-20-29-28-12-11-26(38(24(3)4)40(47(71)58-33)62-43(67)31-13-14-37(65)55-31)18-32(28)56-41(29)63-21-27(54-22-63)19-35(49(73)74)60-42(66)30(9-7-15-53-50(51)52)57-45(69)36-10-8-16-64(36)48(34)72/h11-12,18,21-25,30-31,33-36,38-40,56H,7-10,13-17,19-20H2,1-6H3,(H,55,65)(H,57,69)(H,58,71)(H,59,70)(H,60,66)(H,61,68)(H,62,67)(H,73,74)(H4,51,52,53)/t30-,31-,33-,34-,35-,36-,38+,39-,40-/m0/s1 |
InChI Key |
ZIUCJBZUJCNMSJ-WYHXJWKRSA-N |
Isomeric SMILES |
CC(C)C[C@H]1C(=O)N[C@H](C(=O)N[C@H]2CC3=C(NC4=C3C=CC(=C4)[C@H]([C@@H](C(=O)N1)NC(=O)[C@@H]5CCC(=O)N5)C(C)C)N6C=C(C[C@H](NC(=O)[C@@H](NC(=O)[C@@H]7CCCN7C2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
SMILES |
CC(C)CC1C(=O)NC(C(=O)NC2CC3=C(NC4=C3C=CC(=C4)C(C(C(=O)N1)NC(=O)C5CCC(=O)N5)C(C)C)N6C=C(CC(NC(=O)C(NC(=O)C7CCCN7C2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Canonical SMILES |
CC(C)CC1C(=O)NC(C(=O)NC2CC3=C(NC4=C3C=CC(=C4)C(C(C(=O)N1)NC(=O)C5CCC(=O)N5)C(C)C)N6C=C(CC(NC(=O)C(NC(=O)C7CCCN7C2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Synonyms |
celogentin C |
Origin of Product |
United States |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
Strategy Settings
Precursor scoring | Relevance Heuristic |
---|---|
Min. plausibility | 0.01 |
Model | Template_relevance |
Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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