BIRD-PRD_000194: ACTAGARDINE

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000194
• Status: Status: REF ONLY
• Name: ACTAGARDINE

BIRD information

• Type: Oligopeptide / Lantibiotic

Details

• ACTAGARDINE IS A TRICYCLIC 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 THIOETHER BONDS WITH CYSTEINE RESULT IN THREE RING STRUCTURES. THIS IS FOLLOWED BY MEMBRANE TRANSLOCATION AND CLEAVAGE OF THE MODIFIED PRECURSOR.

• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• ACTAGARDINE (PDB)
• AIDS 187911 (PubChem)
• Actagardine (SciFinder, PubChem)
• Antibiotic A 3802-IV-3 (SciFinder)
• GardimycinActagardin (SciFinder, UniProt, PubChem)
• lantibiotic actagardine (UniProt)

Annotation

• Function: AntibacterialAntibiotic / Info source: NovelAntibiotics
• Function: lantibioticLantibiotics / Info source: Bactibase
• Function: creates aqueous pores in membrane / Info source: Bactibase
• Function: antibacterial activity against Gram-positive bacteria / Info source: UniProt
• Function: good antistreptococcal activity / Info source: UniProt
• Function: murein-biosynthesis-inhibitor / Info source: PubMed: 9219543

Source

• Actinoplanes liguriae, UniProtKB: P56650
• Actinoplanes garbadinensis (bacteria), UniProtKB: P56650

External info

• Bactibase: BAC012
• Beilstein: 90400059
• NovelAntibiotics: 520189
• PubChem: 16204841
• CAS: 59165-34-3
• UniProt: P56650
• [MESH_Unique_ID] MESH: C012993

Family

LantibioticLantibiotics

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

Chemical information

Composition

Formula: C₈₁H₁₂₄N₂₀O₂₃S₄ / Formula weight: 1874.231

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: Too many bonds
• CACTVS 3.370: CC[CH](C)[CH]1NC(=O)[CH](NC(=O)[CH]2NC(=O)CNC(=O)[CH]3CS[CH](C)[CH](NC(=O)[CH]4CSC[CH](N)C(=O)N[CH](CO)C(=O)NCC(=O)N[CH](Cc5c[nH]c6ccccc56)C(=O)N[CH](C(C)C)C(=O)N4)C(=O)N[CH](CC(C)C)C(=O)N[CH]([CH](C)SC[CH](NC1=O)C(=O)N[CH](C)C(=O)N[CH](CS[CH]2C)C(O)=O)C(=O)N[CH]([CH](C)CC)C(=O)N[CH](CCC(O)=O)C(=O)N3)C(C)C
• OpenEye OEToolkits 1.7.6: CCC(C)C1C(=O)NC(C(=O)NC2CSC(C(C(=O)NC(C(=O)NC(C(SCC3C(=O)NC(C(=O)NC(CSC(C(C(=O)NC(C(=O)NC(C(=O)N3)C(C)CC)C(C)C)NC(=O)CNC2=O)C)C(=O)O)C)C)C(=O)N1)CC(C)C)NC(=O)C4CSCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N4)C(C)C)Cc5c[nH]c6c5cccc6)CO)N)C)CCC(=O)O

SMILES CANONICAL

• CACTVS 3.370: CC[C@H](C)[C@@H]1NC(=O)[C@@H](NC(=O)[C@@H]2NC(=O)CNC(=O)[C@@H]3CS[C@@H](C)[C@@H](NC(=O)[C@@H]4CSC[C@@H](N)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](Cc5c[nH]c6ccccc56)C(=O)N[C@@H](C(C)C)C(=O)N4)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]([C@H](C)SC[C@H](NC1=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CS[C@H]2C)C(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N3)C(C)C
• OpenEye OEToolkits 1.7.6: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H]2CSC([C@H](C(=O)N[C@H](C(=O)N[C@H](C(SC[C@H]3C(=O)N[C@H](C(=O)N[C@@H](CSC([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N3)[C@@H](C)CC)C(C)C)NC(=O)CNC2=O)C)C(=O)O)C)C)C(=O)N1)CC(C)C)NC(=O)[C@@H]4CSC[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N4)C(C)C)Cc5c[nH]c6c5cccc6)CO)N)C)CCC(=O)O

InChI

• InChI 1.03: InChI=1S/C81H124N20O23S4/c1-15-37(9)60-76(118)88-47(21-22-57(105)106)69(111)91-52-31-126-41(13)63(101-73(115)51-30-125-29-45(82)66(108)90-50(28-102)67(109)84-26-55(103)87-49(71(113)96-58(35(5)6)74(116)92-51)24-43-25-83-46-20-18-17-19-44(43)46)78(120)89-48(23-34(3)4)70(112)100-64(80(122)99-60)42(14)127-32-53-72(114)86-39(11)65(107)94-54(81(123)124)33-128-40(12)62(95-56(104)27-85-68(52)110)79(121)97-59(36(7)8)75(117)98-61(38(10)16-2)77(119)93-53/h17-20,25,34-42,45,47-54,58-64,83,102H,15-16,21-24,26-33,82H2,1-14H3,(H,84,109)(H,85,110)(H,86,114)(H,87,103)(H,88,118)(H,89,120)(H,90,108)(H,91,111)(H,92,116)(H,93,119)(H,94,107)(H,95,104)(H,96,113)(H,97,121)(H,98,117)(H,99,122)(H,100,112)(H,101,115)(H,105,106)(H,123,124)/t37-,38-,39-,40-,41-,42-,45+,47-,48-,49-,50-,51-,52-,53-,54-,58-,59-,60-,61-,62+,63+,64+/m0/s1

InChIKey

• InChI 1.03: BONKUOOMLCEDCZ-UAPKJGFDSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (1R,4S,5S,8S,11S,12S,15R,21S,22S,25R,28S,33S,36S,41S,44S)-11-({[(3R,6S,9S,15S,18S)-18-amino-15-(hydroxymethyl)-9-(1H-indol-3-ylmethyl)-5,8,11,14,17-pentaoxo-6-(propan-2-yl)-1-thia-4,7,10,13,16-pentaazacyclononadecan-3-yl]carbonyl}amino)-33,44-di[(2S)-butan-2-yl]-41-(2-carboxyethyl)-4,12,22,28-tetramethyl-8-(2-methylpropyl)-7,10,16,19,27,30,32,35,38,40,43,46-dodecaoxo-36-(propan-2-yl)-3,13,23-trithia-6,9,17,20,26,29,31,34,37,39,42,45-dodecaazatricyclo[19.9.8.8~5,15~]hexatetracontane-25-carboxylic acid #

PDB entries

Showing all 1 items

PDB-1aj1:
NMR STRUCTURE OF THE LANTIBIOTIC ACTAGARDINE