CHEBI:71658 - mersacidin

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ChEBI Name mersacidin
ChEBI ID CHEBI:71658
Definition A type-B lantibiotic containing 3-methyllanthionine and S-(2-aminovinyl)-3-methylcysteine residues and four intra-chain thioether bridges. It is obtained from Bacillus sp. HIL Y-85,54728 and is active in vivo against methicillin-resistant Staphylococcus aureus (MRSA).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C80H120N20O21S4
Net Charge 0
Average Mass 1826.19000
Monoisotopic Mass 1824.782
InChI InChI=1S/C80H120N20O21S4/c1-14-40(8)61-74(115)82-24-26-122-42(10)62-76(117)87-41(9)66(107)88-48(22-23-59(105)106)68(109)92-52(71(112)95-61)35-124-44(12)64(78(119)89-49(27-37(2)3)69(110)97-62)99-72(113)53-36-125-45(13)65(98-70(111)50(29-46-19-16-15-17-20-46)90-77(118)63-43(11)123-34-47(81)67(108)96-63)79(120)91-51(28-38(4)5)80(121)100-25-18-21-54(100)73(114)86-32-57(103)84-30-55(101)83-31-56(102)85-33-58(104)94-60(39(6)7)75(116)93-53/h15-17,19-20,24,26,37-40,42-45,47-54,60-65H,9,14,18,21-23,25,27-36,81H2,1-8,10-13H3,(H,82,115)(H,83,101)(H,84,103)(H,85,102)(H,86,114)(H,87,117)(H,88,107)(H,89,119)(H,90,118)(H,91,120)(H,92,109)(H,93,116)(H,94,104)(H,95,112)(H,96,108)(H,97,110)(H,98,111)(H,99,113)(H,105,106)/b26-24+/t40-,42+,43+,44+,45+,47+,48+,49+,50+,51+,52+,53+,54+,60+,61+,62?,63-,64-,65-/m1/s1
InChIKey JSWKNDSDVHJUKY-CYGWNLPQSA-N
SMILES [H][C@@]1(C)SC[C@@H]2NC(=O)[C@H](CCC(O)=O)NC(=O)C(=C)NC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1NC(=O)[C@@H]1CS[C@@H](C)[C@@]([H])(NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@]3([H])NC(=O)[C@@H](N)CS[C@H]3C)C(=O)N[C@@]([H])(CC(C)C)C(=O)N3CCC[C@@]3([H])C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N1)[C@H](C)S\C=C\NC(=O)[C@@]([H])(NC2=O)[C@H](C)CC
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.
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 mersacidin (CHEBI:71658) has role antibacterial agent (CHEBI:33282)
mersacidin (CHEBI:71658) has role metabolite (CHEBI:25212)
mersacidin (CHEBI:71658) is a macrocycle (CHEBI:51026)
mersacidin (CHEBI:71658) is a type B lantibiotic (CHEBI:71647)
mersacidin (CHEBI:71658) is tautomer of mersacidin zwitterion (CHEBI:91014)
Incoming mersacidin zwitterion (CHEBI:91014) is tautomer of mersacidin (CHEBI:71658)
IUPAC Name
3-{(4S,7S,8S,11R,14S,17E,20S,26S)-7-[({(15S,18R,21S,22S,25S,30aS)-22-[(N-{[(2S,3S,6R)-6-amino-2-methyl-5-oxo-1,4-thiazepan-3-yl]carbonyl}-L-phenylalanyl)amino]-25-isobutyl-15-isopropyl-21-methyl-1,4,7,10,13,16,23,26-octaoxooctacosahydro-1H-pyrrolo[2,1-u][1,4,7,10,13,16,19,22,25]thiaoctaazacyclooctacosin-18-yl}carbonyl)amino]-14-[(2R)-butan-2-yl]-4-isobutyl-8,20-dimethyl-23-methylene-3,6,12,15,21,24,27-heptaoxo-9,19-dithia-2,5,13,16,22,25,28-heptaazabicyclo[9.9.8]octacos-17-en-26-yl}propanoic acid
Synonym Source
M87-1551 ChEBI
Registry Numbers Types Sources
128104-18-7 CAS Registry Number ChemIDplus
8197141 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10818347 PubMed citation Europe PMC
10831439 PubMed citation Europe PMC
1500347 PubMed citation Europe PMC
1500348 PubMed citation Europe PMC
15282239 PubMed citation Europe PMC
1649577 PubMed citation Europe PMC
16980420 PubMed citation Europe PMC
21811596 PubMed citation Europe PMC
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22628498 PubMed citation Europe PMC
7737474 PubMed citation Europe PMC
Last Modified
25 January 2013