mersacidin (CHEBI:71658)

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CHEBI:71658 - mersacidin

ChEBI ID	CHEBI:71658
ChEBI Name	mersacidin
Stars
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).
Last Modified	25 January 2013
Submitter	Gareth Owen
Downloads	Molfile

Formula	C80H120N20O21S4
Net Charge	0
Average Mass	1826.227
Monoisotopic Mass	1824.78197
SMILES	[H][C@]1(NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@]2([H])NC(=O)[C@@H](N)CS[C@H]2C)C(=O)N[C@@]([H])(CC(C)C)C(=O)N2CCC[C@@]2([H])C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NC3C(=O)NC(=C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CS[C@@]2([H])C)C(=O)N[C@@]([H])([C@H](C)CC)C(=O)N/C=C/S[C@H]3C)CS[C@H]1C
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

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)
	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 Relation(s)
Incoming Relation(s)	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

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	Sources
Reaxys:8197141	Reaxys
CAS:128104-18-7	ChemIDplus

Citations