BIRD-PRD_000184: Microcin J25

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000184
• Status: Status: REF ONLY
• Name: Microcin J25

BIRD information

• Type: Polypeptide / Inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• Microcin J25 (PDB)

Annotation

• Mechanism of Action: Peptide antibiotic that functions through inhibition of the bacterial DNA-dependent RNA polymerase (RNAP). May inhibit transcription by binding in RNAP secondary channel and blocking nucleotide substrates access to the catalytic center. Also acts on the cytoplasmic membrane of Salmonella newport, producing alteration of membrane permeability and disruption of the subsequent gradient dissipation, which inhibits several processes essential for cell viability, such as oxygen consumption. Induces bacterial filamentation in susceptible cells in a non-SOS-dependent way, but this phenotype may result from impaired transcription of genes coding for cell division proteins. / Info source: Bactibase

Source

• Escherichia coli (E. coli), UniProtKB: Q9X2V7

External info

• Bactibase: BAC015
• UniProt: Q9X2V7

Family

Microcin

Microcin C7 / Microcin J25 / Selenomethionine derivative of Microcin C7 / Microcin C7 iso-ASN analog

Chemical information

Composition

Formula: C₁₀₁H₁₄₀N₂₃O₂₇ / Formula weight: 2108.33

• Others: Type: peptide-like

History

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• CACTVS 3.370: CC[CH](C)[CH](NC(=O)CNC(=O)[CH](NC(=O)[CH](Cc1ccccc1)NC(=O)[CH](Cc2ccc(O)cc2)NC(=O)[CH]3CCC(=O)NCC(=O)NCC(=O)N[CH](C)C(=O)NCC(=O)N[CH](Cc4c[nH]c[nH+]4)C(=O)N[CH](C(C)C)C(=O)N5CCC[CH]5C(=O)N3)C(C)C)C(=O)NCC(=O)N[CH]([CH](C)O)C(=O)N6CCC[CH]6C(=O)N[CH]([CH](C)CC)C(=O)N[CH](CO)C(=O)N[CH](Cc7ccccc7)C(=O)N[CH](Cc8ccc(O)cc8)C(=O)NCC(O)=O
• OpenEye OEToolkits 1.7.6: CCC(C)C(C(=O)NCC(=O)NC(C(C)O)C(=O)N1CCCC1C(=O)NC(C(C)CC)C(=O)NC(CO)C(=O)NC(Cc2ccccc2)C(=O)NC(Cc3ccc(cc3)O)C(=O)NCC(=O)O)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(Cc4ccccc4)NC(=O)C(Cc5ccc(cc5)O)NC(=O)C6CCC(=O)NCC(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N7CCCC7C(=O)N6)C(C)C)Cc8c[nH]c[nH+]8)C

SMILES CANONICAL

• CACTVS 3.370: CC[C@H](C)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H]3CCC(=O)NCC(=O)NCC(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](Cc4c[nH]c[nH+]4)C(=O)N[C@@H](C(C)C)C(=O)N5CCC[C@H]5C(=O)N3)C(C)C)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N6CCC[C@H]6C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc7ccccc7)C(=O)N[C@@H](Cc8ccc(O)cc8)C(=O)NCC(O)=O
• OpenEye OEToolkits 1.7.6: CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc3ccc(cc3)O)C(=O)NCC(=O)O)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@H](Cc5ccc(cc5)O)NC(=O)[C@@H]6CCC(=O)NCC(=O)NCC(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N7CCC[C@H]7C(=O)N6)C(C)C)Cc8c[nH]c[nH+]8)C

InChI

• InChI 1.03: InChI=1S/C101H139N23O27/c1-11-55(7)84(98(148)107-49-80(134)119-86(58(10)126)101(151)124-38-20-26-74(124)96(146)122-85(56(8)12-2)99(149)117-72(51-125)94(144)116-68(39-59-21-15-13-16-22-59)90(140)113-67(88(138)108-50-81(135)136)41-61-27-31-64(127)32-28-61)118-79(133)48-106-97(147)82(53(3)4)120-92(142)70(40-60-23-17-14-18-24-60)115-91(141)69(42-62-29-33-65(128)34-30-62)114-89(139)66-35-36-75(129)103-45-76(130)104-46-77(131)110-57(9)87(137)105-47-78(132)111-71(43-63-44-102-52-109-63)93(143)121-83(54(5)6)100(150)123-37-19-25-73(123)95(145)112-66/h13-18,21-24,27-34,44,52-58,66-74,82-86,125-128H,11-12,19-20,25-26,35-43,45-51H2,1-10H3,(H,102,109)(H,103,129)(H,104,130)(H,105,137)(H,106,147)(H,107,148)(H,108,138)(H,110,131)(H,111,132)(H,112,145)(H,113,140)(H,114,139)(H,115,141)(H,116,144)(H,117,149)(H,118,133)(H,119,134)(H,120,142)(H,121,143)(H,122,146)(H,135,136)/p+1/t55-,56-,57-,58+,66-,67-,68-,69-,70-,71-,72-,73-,74-,82-,83-,84-,85-,86-/m0/s1

InChIKey

• InChI 1.03: FRJVEVHOMWPHHN-UBTJVNBSSA-O

SYSTEMATIC NAME

• OpenEye OEToolkits 1.7.6: 2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-1-[(2S,3R)-2-[2-[[(2S,3S)-2-[2-[[(2S)-2-[[(2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(3S,6S,12S,23S,26S)-6-(1H-imidazol-3-ium-4-ylmethyl)-12-methyl-2,5,8,11,14,17,20,25-octakis(oxidanylidene)-3-propan-2-yl-1,4,7,10,13,16,19,24-octazabicyclo[24.3.0]nonacosan-23-yl]carbonylamino]propanoyl]amino]-3-phenyl-propanoyl]amino]-3-methyl-butanoyl]amino]ethanoylamino]-3-methyl-pentanoyl]amino]ethanoylamino]-3-oxidanyl-butanoyl]pyrrolidin-2-yl]carbonylamino]-3-methyl-pentanoyl]amino]-3-oxidanyl-propanoyl]amino]-3-phenyl-propanoyl]amino]propanoyl]amino]ethanoic acid #

PDB entries

Showing all 4 items

PDB-1pp5:
Structure of Antibacterial Peptide Microcin J25: a 21-Residue Lariat Protoknot

PDB-1q71:
The structure of microcin J25 is a threaded sidechain-to-backbone ring structure and not a head-to-tail cyclized backbone

PDB-4cu4:
FhuA from E. coli in complex with the lasso peptide microcin J25 (MccJ25)

PDB-6n60:
Escherichia coli RNA polymerase sigma70-holoenzyme bound to upstream fork promoter DNA and Microcin J25 (MccJ25)