CHEBI:71659 - epidermin

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ChEBI Name epidermin
ChEBI ID CHEBI:71659
Definition A type A lantibiotic that is a tetracyclic 21-amino-acid peptide which contains meso-lanthionine, 3-methyllanthionine, and S-(2-aminovinyl)-D-cysteine. It is obtained from Staphylococcus epidermidis Tü 3298 and exhibits antibiotic activity against many Gram-positive bacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C98H141N25O23S4
Net Charge 0
Average Mass 2165.58200
Monoisotopic Mass 2163.951
InChI InChI=1S/C98H141N25O23S4/c1-9-51(4)77(102)96(144)107-54(7)81(129)117-70-48-149-49-71(120-97(145)78(52(5)10-2)121-89(137)65(40-57-25-16-13-17-26-57)113-85(133)62(112-92(70)140)28-19-21-35-100)94(142)122-79-55(8)150-50-72(109-76(127)44-105-95(143)73-29-22-37-123(73)98(79)146)90(138)106-53(6)80(128)111-61(27-18-20-34-99)84(132)110-60(11-3)82(130)104-43-75(126)108-68-47-148-46-67-83(131)103-36-38-147-45-69(93(141)115-64(87(135)118-67)41-58-30-32-59(124)33-31-58)119-88(136)66(42-74(101)125)116-86(134)63(114-91(68)139)39-56-23-14-12-15-24-56/h11-17,23-26,30-33,36,38,51-55,61-73,77-79,124H,9-10,18-22,27-29,34-35,37,39-50,99-100,102H2,1-8H3,(H2,101,125)(H,103,131)(H,104,130)(H,105,143)(H,106,138)(H,107,144)(H,108,126)(H,109,127)(H,110,132)(H,111,128)(H,112,140)(H,113,133)(H,114,139)(H,115,141)(H,116,134)(H,117,129)(H,118,135)(H,119,136)(H,120,145)(H,121,137)(H,122,142)/b38-36-,60-11-/t51-,52-,53-,54-,55-,61-,62-,63-,64-,65-,66-,67-,68+,69+,70+,71-,72-,73-,77-,78-,79+/m0/s1
InChIKey CXTXHTVXPMOOSW-JUEJINBGSA-N
SMILES [H][C@]1(CS[C@@H](C)[C@@H](NC(=O)[C@@H]2CSC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](N)[C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N2)C(=O)N2CCC[C@@]2([H])C(=O)NCC(=O)N1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N\C(=C/C)C(=O)NCC(=O)N[C@@H]1CSC[C@@H]2NC(=O)[C@]([H])(Cc3ccc(O)cc3)NC(=O)[C@@H](CS\C=C/NC2=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc2ccccc2)NC1=O
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): antibacterial agent
A substance that kills or slows the growth of bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 epidermin (CHEBI:71659) has role antibacterial agent (CHEBI:33282)
epidermin (CHEBI:71659) has role metabolite (CHEBI:25212)
epidermin (CHEBI:71659) is a macrocycle (CHEBI:51026)
epidermin (CHEBI:71659) is a type A lantibiotic (CHEBI:71645)
IUPAC Name
N-({(6R,9S,10S,15aS)-10-[({(3R,6S,9S,12S,15S)-12-(4-aminobutyl)-9-benzyl-6-[(2S)-butan-2-yl]-15-[(L-isoleucyl-L-alanyl)amino]-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetraazacyclohexadecan-3-yl}carbonyl)amino]-9-methyl-1,4,11-trioxododecahydro-1H,9H-pyrrolo[2,1-i][1,4,7,10]thiatriazacyclotridecin-6-yl}carbonyl)-L-alanyl-N-{(2Z)-1-[(2-{[(1S,4S,7S,10S,14R,17Z,23S)-4-(2-amino-2-oxoethyl)-7-benzyl-23-(4-hydroxybenzyl)-3,6,9,15,21,24-hexaoxo-12,19-dithia-2,5,8,16,22,25-hexaazabicyclo[12.6.5]pentacos-17-en-10-yl]amino}-2-oxoethyl)amino]-1-oxobut-2-en-2-yl}-L-lysinamide
Synonym Source
staphylococcin 1580 ChEBI
Manual Xref Database
EP0350810 Patent
View more database links
Registry Numbers Types Sources
11305595 Reaxys Registry Number Reaxys
99165-17-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1551392 PubMed citation Europe PMC
16586024 PubMed citation Europe PMC
3769923 PubMed citation Europe PMC
8135526 PubMed citation Europe PMC
8775972 PubMed citation Europe PMC
Last Modified
28 January 2013