mersacidin   Click here for help

GtoPdb Ligand ID: 11014

Synonyms: M87 1551 | M87-1551
Compound class: Natural product or derivative
Comment: Mersacidin is a type-B lantibacterial that is produced by Bacillus sp. HIL Y-85,54728. It is active in vivo against methicillin-resistant Staphylococcus aureus (MRSA) [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 41
Hydrogen bond donors 20
Rotatable bonds 21
Topological polar surface area 708.63
Molecular weight 1824.78
XLogP 5.61
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC[C@H]([C@@H]1NC(=O)[C@@H]2CS[C@@H](C)[C@@H](NC(=O)[C@@H]3CS[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]4NC(=O)[C@H](CS[C@H]4C)N)Cc4ccccc4)C(=O)N[C@@H](CC(C)C)C(=O)N4CCC[C@H]4C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)N[C@H](C(=O)N3)C(C)C)C(=O)N[C@H](C(=O)NC([C@@H](S/C=C/NC1=O)C)C(=O)NC(=C)C(=O)N[C@H](C(=O)N2)CCC(=O)O)CC(C)C)C
Isomeric SMILES CC[C@H]([C@@H]1NC(=O)[C@@H]2CS[C@@H](C)[C@@H](NC(=O)[C@@H]3CS[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]4NC(=O)[C@H](CS[C@H]4C)N)Cc4ccccc4)C(=O)N[C@@H](CC(C)C)C(=O)N4CCC[C@H]4C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)N[C@H](C(=O)N3)C(C)C)C(=O)N[C@H](C(=O)NC([C@@H](S/C=C/NC1=O)C)C(=O)NC(=C)C(=O)N[C@H](C(=O)N2)CCC(=O)O)CC(C)C)C
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
InChI Key JSWKNDSDVHJUKY-CYGWNLPQSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
3-[(4S,7S,8S,11R,14S,17E,20S,26S)-7-[[(3S,6S,7S,10R,13S,28S)-6-[[(2S)-2-[[(2S,3S,6R)-6-amino-2-methyl-5-oxo-1,4-thiazepane-3-carbonyl]amino]-3-phenylpropanoyl]amino]-7-methyl-3-(2-methylpropyl)-2,5,12,15,18,21,24,27-octaoxo-13-propan-2-yl-8-thia-1,4,11,14,17,20,23,26-octazabicyclo[26.3.0]hentriacontane-10-carbonyl]amino]-14-[(2R)-butan-2-yl]-8,20-dimethyl-23-methylidene-4-(2-methylpropyl)-3,6,12,15,21,24,27-heptaoxo-9,19-dithia-2,5,13,16,22,25,28-heptazabicyclo[9.9.8]octacos-17-en-26-yl]propanoic acid
Synonyms Click here for help
M87 1551 | M87-1551
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Mersacidin, M87 1551
Other databases
ChEBI CHEBI:71658
GtoPdb PubChem SID 405560455
PubChem CID 70698380
Search Google for chemical match using the InChIKey JSWKNDSDVHJUKY-CYGWNLPQSA-N
Search Google for chemicals with the same backbone JSWKNDSDVHJUKY
UniChem Compound Search for chemical match using the InChIKey JSWKNDSDVHJUKY-CYGWNLPQSA-N
UniChem Connectivity Search for chemical match using the InChIKey JSWKNDSDVHJUKY-CYGWNLPQSA-N