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- BIRD-PRD_000195: Cinnamycin -

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Basic information

EntryDatabase: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000195
StatusStatus: REF ONLY
NameCinnamycin
WikipediaWikipedia - Cinnamycin: Cinnamycin is a tetracyclic antibacterial peptide produced by Streptomyces cinnamoneus containing 19 amino acid residues including the unusual amino acids threo-3-methyl-lanthionine, meso-lanthionine, lysinoalanine, and 3-hydroxyaspartic acid.

Cinnamycin belongs to the class of molecules known as lantibiotics which belongs to ribosomally synthesized post-translationally modified peptides. The unique receptor for cinnamycin is phosphatidylethanolamine (PE) lipids which is a major compound present in many bacterial cell membranes.

Cinnamycin was first isolated in 1952 and some other compounds with similar sequence and structure were found later.

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BIRD information

TypePolypeptide / Lantibiotic
Details
  • CINNAMYCIN IS A GLOBULAR TYPE B LANTIBIOTIC. THE LANTIBIOTICS ARE CHARACTERIZED BY THIOESTER AMINO ACIDS LANTHIONINE AND/OR METHYLLANTHIONINE. HERE, CINNAMYCIN IS REPRESENTED BY THE SEQUENCE (SEQRES)
  • CINNAMYCIN IS A TETRACYCLIC PEPTIDE. POST TRANSLATIONAL MATURATION OF LANTIBIOTICS INVOLVES THE ENZYMIC CONVERSION OF THR AND SER INTO DEHYDRATED AMINO ACIDS AND THE FORMATION OF THIOETHER BONDS WITH CYSTEINE. THE 14-19 BETA-METHYLLANTHIONINE THIOETHER BOND IS OXIDIZED TO A SULFOXIDE. THE THIOETHER BONDS WITH CYSTEINE RESULT IN THREE RING STRUCTURES, CROSSLINK BETWEEN SER AND LYS RESULT IN THE FOURTH RING. THIS IS FOLLOWED BY MEMBRANE TRANSLOCATION AND CLEAVAGE OF THE MODIFIED PRECURSOR.
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • CINNAMYCIN (PDB)
  • Cinnamycin, hydrochloride (9CI) (SciFinder)
  • Lanthiopeptin (SciFinder, UniProt, PubChem)
  • Lantibiotic Ro 09-0198 (UniProt)
  • NSC 71936 (PubChem)
  • Ro 09-0198 (SciFinder, PubChem)
Annotation
  • Function: AntiviralAntiviral drug / Info source: NovelAntibiotics
  • Function: enzyme inhibitor of phospholipase A2 and of angiotensin-converting enzyme / Info source: Bactibase
  • Function: exhibits immunopotentiating and inhibitory activity against herpes simplex virus / Info source: Bactibase
  • Function: inhibitor of the enzymes phospholipase A2, and angiotensin-converting enzyme / Info source: UniProt
  • Function: Shows inhibitory activities against herpes simplex virus and immunopotentiating activities / Info source: UniProt
Source
External info
FamilyLantibioticLantibiotics

ACTAGARDINE / Cinnamycin / EPILANCIN 15X ...ACTAGARDINE / Cinnamycin / EPILANCIN 15X / BIRD: PRD_000197 / BETA LICHENICIDIN PREPEPTIDE / Mersacidin / Nisin A

Related structures
  • cysteinyl-(alpha-aminobutyryl)-phenylalanyl-(alpha-aminobutyryl)-leucyl-prolyl-glycyl-glycyl-glycyl-glycyl-valyl-cysteinyl-(alpha-aminobutyryl)-leucyl-(alpha-aminobutyryl)-(dehydroalanyl)-glutamyl-cysteinyl-isoleucine 2-sulfanylethenylamide methanol solvate hydrate, Mersacidin methanol solvate hydrate, seqres C9 CYS*!,GLY!-LEU-PRO-GLY-GLY-GLY-GLY-VAL-, C6 ALA!,CYS*!-LEU-CYS*-ALA*-GLU-, C2 CYS*-GLY!, A3 GLY!-PHE-GLY!, A2 ALA!-ILE, A2 CYS*!-CYS*! / CCDC: WOPCAF / Reference

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Chemical information

Composition
Formula: C89H127N25O25S3 / Formula weight: 2043.308
OthersType: peptide-like
History
External linksUniChem / ChemSpider / Wikipedia search / Google search

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Structure visualization

Structure viewerMolecule:
MolmilJmol/JSmol

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Details

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SMILES

CACTVS 3.370CC(C)[CH]1NC(=O)[CH](Cc2ccccc2)NC(=O)[CH]3NC(=O)[CH](Cc4ccccc4)NC(=O)[CH]5CCCN5C(=O)CNC(=O)[CH](Cc6ccccc6)NC(=O)[CH]7C[NH2+]CCCC[CH](NC(=O)[CH]8NC(=O)[CH](CC(N)=O)NC(=O)CNC(=O)[CH](NC(=O)[CH](CSC[CH](NC(=O)[CH](CCC(N)=O)NC(=O)[CH](CCCNC(N)=[NH2+])NC(=O)[CH](N)CS[CH]8C)C(=O)N[CH](CS[CH]3C)C(=O)N7)NC1=O)[CH](O)C(O)=O)C(O)=O
OpenEye OEToolkits 1.7.6CC1C2C(=O)NC(C(=O)NC(C(=O)NC3CSCC4C(=O)NC(CS1)C(=O)NC(C[NH2+]CCCCC(NC(=O)C(C(SCC(C(=O)NC(C(=O)NC(C(=O)N4)CCC(=O)N)CCCNC(=[NH2+])N)N)C)NC(=O)C(NC(=O)CNC(=O)C(NC3=O)C(C(=O)O)O)CC(=O)N)C(=O)O)C(=O)NC(C(=O)NCC(=O)N5CCCC5C(=O)NC(C(=O)N2)Cc6ccccc6)Cc7ccccc7)C(C)C)Cc8ccccc8

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SMILES CANONICAL

CACTVS 3.370CC(C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]3NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@@H]5CCCN5C(=O)CNC(=O)[C@H](Cc6ccccc6)NC(=O)[C@@H]7C[NH2+]CCCC[C@H](NC(=O)[C@@H]8NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CSC[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H](N)CS[C@H]8C)C(=O)N[C@@H](CS[C@H]3C)C(=O)N7)NC1=O)[C@@H](O)C(O)=O)C(O)=O
OpenEye OEToolkits 1.7.6CC1[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H]3CSC[C@@H]4C(=O)N[C@@H](CS1)C(=O)N[C@@H](C[NH2+]CCCC[C@H](NC(=O)[C@@H](C(SC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N4)CCC(=O)N)CCCNC(=[NH2+])N)N)C)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC3=O)[C@H](C(=O)O)O)CC(=O)N)C(=O)O)C(=O)N[C@H](C(=O)NCC(=O)N5CCC[C@H]5C(=O)N[C@H](C(=O)N2)Cc6ccccc6)Cc7ccccc7)C(C)C)Cc8ccccc8

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InChI

InChI 1.03InChI=1S/C89H125N25O25S3/c1-43(2)66-84(133)109-59-41-140-40-58-79(128)108-60-42-142-45(4)68(86(135)105-55(75(124)110-66)34-48-22-12-7-13-23-48)111-76(125)54(33-47-20-10-6-11-21-47)104-82(131)61-26-17-31-114(61)65(118)38-98-72(121)53(32-46-18-8-5-9-19-46)103-78(127)57(106-80(60)129)36-95-29-15-14-24-52(87(136)137)102-85(134)67(112-77(126)56(35-63(92)116)99-64(117)37-97-83(132)69(113-81(59)130)70(119)88(138)139)44(3)141-39-49(90)71(120)100-50(25-16-30-96-89(93)94)73(122)101-51(74(123)107-58)27-28-62(91)115/h5-13,18-23,43-45,49-61,66-70,95,119H,14-17,24-42,90H2,1-4H3,(H2,91,115)(H2,92,116)(H,97,132)(H,98,121)(H,99,117)(H,100,120)(H,101,122)(H,102,134)(H,103,127)(H,104,131)(H,105,135)(H,106,129)(H,107,123)(H,108,128)(H,109,133)(H,110,124)(H,111,125)(H,112,126)(H,113,130)(H,136,137)(H,138,139)(H4,93,94,96)/p+2/t44-,45-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58+,59-,60-,61-,66-,67+,68+,69-,70+/m0/s1

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InChIKey

InChI 1.03QJDWKBINWOWJNZ-OURZNGJWSA-P

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PDB entries

Showing all 1 items

PDB-2dde:
Structure of cinnamycin complexed with lysophosphatidylethanolamine

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