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CHEBI:71659 - epidermin

ChEBI IDCHEBI:71659
ChEBI Nameepidermin
Stars
DefinitionA 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.
Last Modified28 January 2013
SubmitterGareth Owen
DownloadsMolfile
FormulaC98H141N25O23S4
Net Charge0
Average Mass2165.626
Monoisotopic Mass2163.95150
SMILES[H][C@@]12CCCN1C(=O)[C@H](NC(=O)[C@@H]1CSC[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)N1)[C@H](C)SC[C@@]([H])(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]3NC(=O)[C@]([H])(Cc4ccc(O)cc4)NC(=O)[C@@H](CS/C=C\NC3=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc3ccccc3)NC1=O)NC(=O)CNC2=O
InChIInChI=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
InChIKeyCXTXHTVXPMOOSW-JUEJINBGSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
antibacterial agent  A substance (or active part thereof) 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.
ChEBI Ontology
Outgoing Relation(s)
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 1580ChEBI
Manual XrefsDatabases
EP0350810Patent
Registry NumbersSources
Reaxys:11305595Reaxys
CAS:99165-17-0ChemIDplus
Citations