CHEBI:29701 - tyrocidine A

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ChEBI Name tyrocidine A
ChEBI ID CHEBI:29701
Definition A homodetic cyclic decapeptide consisting of D-Phe, L-Pro, L-Phe, D-Phe, L-Asn, L-Gln, L-Tyr, L-Val, L-Orn, and L-Leu residues coupled in sequence and cyclised head-to-tail.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C66H87N13O13
Net Charge 0
Average Mass 1270.47630
Monoisotopic Mass 1269.655
InChI InChI=1S/C66H87N13O13/c1-38(2)32-47-59(85)77-52(36-42-20-12-7-13-21-42)66(92)79-31-15-23-53(79)64(90)76-49(34-41-18-10-6-11-19-41)61(87)74-48(33-40-16-8-5-9-17-40)60(86)75-51(37-55(69)82)62(88)70-46(28-29-54(68)81)58(84)73-50(35-43-24-26-44(80)27-25-43)63(89)78-56(39(3)4)65(91)71-45(22-14-30-67)57(83)72-47/h5-13,16-21,24-27,38-39,45-53,56,80H,14-15,22-23,28-37,67H2,1-4H3,(H2,68,81)(H2,69,82)(H,70,88)(H,71,91)(H,72,83)(H,73,84)(H,74,87)(H,75,86)(H,76,90)(H,77,85)(H,78,89)/t45-,46-,47-,48+,49-,50-,51-,52+,53-,56-/m0/s1
InChIKey GSXRBRIWJGAPDU-BBVRJQLQSA-N
SMILES [H][C@@]1(Cc2ccc(O)cc2)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@]2([H])CCCN2C(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@@H](NC1=O)C(C)C
Metabolite of Species Details
Brevibacillus brevis (NCBI:txid1393) of strain ATCC 8185 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): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial agent
A substance that kills or slows the growth of bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via peptide antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tyrocidine A (CHEBI:29701) has role antibacterial agent (CHEBI:33282)
tyrocidine A (CHEBI:29701) has role bacterial metabolite (CHEBI:76969)
tyrocidine A (CHEBI:29701) is a homodetic cyclic peptide (CHEBI:24613)
tyrocidine A (CHEBI:29701) is a macrocycle (CHEBI:51026)
tyrocidine A (CHEBI:29701) is a peptide antibiotic (CHEBI:25903)
Incoming tyrocidine (CHEBI:71947) has part tyrocidine A (CHEBI:29701)
IUPAC Name
cyclo(L-asparaginyl-L-glutaminyl-L-tyrosyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-phenylalanyl-D-phenylalanyl)
Synonyms Sources
cyclo-(D-Phe-Pro-Phe-D-Phe-Asn-Gln-Tyr-Val-Orn-Leu) ChEBI
cyclo-(D-PheProPhe-D-PheAsnGlnTyrValOrnLeu) ChEBI
TrcA ChEBI
Manual Xref Database
C12041 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
505927 Reaxys Registry Number Reaxys
8011-61-8 CAS Registry Number KEGG COMPOUND
Citations Waiting for Citations Types Sources
4320358 PubMed citation Europe PMC
5900549 PubMed citation Europe PMC
Last Modified
27 March 2015