BIRD-PRD_001070: Bacitracin A1

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_001070
• Status: Status: REF ONLY
• Name: Bacitracin A1

BIRD information

• Type: Cyclic peptide / Antibiotic

Details

• Ile-1 and Cys-2 have undergone a condensation reaction to produce a thiazoline ring

• Downloads: Molecular definition / Chemical definition

Source

• Bacillus subtilis (bacteria), :

Chemical information

Composition

Formula: C₆₆H₁₀₆N₁₇O₁₆S / Formula weight: 1425.717

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(O)CC2NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1NC(SC1)C(N)C(C)CC)CC(C)C)CCC(=O)O)C(C)CC)CCCC[NH2+]C(=O)C(NC2=O)CC(=O)N)CCCN)C(CC)C)Cc3ccccc3)Cc4[nH+]cnc4
• CACTVS 3.370: CC[CH](C)[CH](N)[C]1N[CH](CS1)C(=O)N[CH](CC(C)C)C(=O)N[CH](CCC(O)=O)C(=O)N[CH]([CH](C)CC)C(=O)N[CH]2CCCC[NH2+]C(=O)[CH](CC(N)=O)NC(=O)[CH](CC(O)=O)NC(=O)[CH](Cc3c[nH]c[nH+]3)NC(=O)[CH](Cc4ccccc4)NC(=O)[CH](NC(=O)[CH](CCCN)NC2=O)[CH](C)CC
• OpenEye OEToolkits 1.7.6: CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)[NH2+]CCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CS[C](N2)C(C(C)CC)N)CC(=O)N)CC(=O)O)Cc3c[nH]c[nH+]3)Cc4ccccc4

SMILES CANONICAL

• CACTVS 3.370: CC[C@H](C)[C@H](N)[C]1N[C@@H](CS1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H]2CCCC[NH2+]C(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](Cc3c[nH]c[nH+]3)NC(=O)[C@@H](Cc4ccccc4)NC(=O)[C@@H](NC(=O)[C@@H](CCCN)NC2=O)[C@@H](C)CC
• OpenEye OEToolkits 1.7.6: CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)[NH2+]CCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CS[C](N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)Cc3c[nH]c[nH+]3)Cc4ccccc4

InChI

• InChI 1.03: InChI=1S/C66H105N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54,66,81H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/p+2/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-,66?/m0/s1

InChIKey

• InChI 1.03: PDIMUPIHARQWSO-WMIXOUNKSA-P

SYSTEMATIC NAME

• ACDLabs 12.01: N-({(2S,4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-1,3-thiazolidin-4-yl}carbonyl)-L-leucyl-D-alpha-glutamyl-N-[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxymethyl)-9-(1H-imidazol-3-ium-4-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-4,7,10,13,16,19-hexaaza-1-azoniacyclopentacosan-21-yl]-L-isoleucinamide
• OpenEye OEToolkits 1.7.6: (4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-azanyl-2-methyl-butyl]-4,5-dihydro-3H-1,3-thiazol-4-yl]carbonylamino]-4-methyl-pentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-azanyl-2-oxidanylidene-ethyl)-18-(3-azanylpropyl)-15-[(2S)-butan-2-yl]-6-(2-hydroxy-2-oxoethyl)-9-(1H-imidazol-3-ium-4-ylmethyl)-2,5,8,11,14,17,20-heptakis(oxidanylidene)-12-(phenylmethyl)-4,7,10,13,16,19-hexaza-1-azoniacyclopentacos-21-yl]amino]-3-methyl-1-oxidanylidene-pentan-2-yl]amino]-5-oxidanylidene-pentanoic acid

PDB entries

Showing all 1 items

PDB-4k7t:
Structure of the ternary complex of bacitracin, zinc, and geranyl-pyrophosphate