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Tyrocidine A

AlkaPlorer ID: AK072908

Synonym: None

IUPAC Name: 3-[(3R,6S,9S,12S,15S,18S,21S,24R,27S,30S)-21-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3,24,27-tribenzyl-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29-decaoxo-12-propan-2-yl-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.3.0]tritriacontan-18-yl]propanamide

Structure

SMILES: CC(C)C[C@@H]1NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](CC2=CC=CC=C2)NC1=O

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InChI: InChI=1S/C66H87N13O13/c1-38(2)32-47-59(85)77-52(36-42-20-12-7-13-21-42)66(92)79-31-15-23-53(79)64(90)76-49(34-41-18-10-6-11-19-41)61(87)74-48(33-40-16-8-5-9-17-40)60(86)75-51(37-55(69)82)62(88)70-46(28-29-54(68)81)58(84)73-50(35-43-24-26-44(80)27-25-43)63(89)78-56(39(3)4)65(91)71-45(22-14-30-67)57(83)72-47/h5-13,16-21,24-27,38-39,45-53,56,80H,14-15,22-23,28-37,67H2,1-4H3,(H2,68,81)(H2,69,82)(H,70,88)(H,71,91)(H,72,83)(H,73,84)(H,74,87)(H,75,86)(H,76,90)(H,77,85)(H,78,89)/t45-,46-,47-,48+,49-,50-,51-,52+,53-,56-/m0/s1

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InChIKey: GSXRBRIWJGAPDU-BBVRJQLQSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Brevibacillus brevis Brevibacillus Paenibacillaceae Bacillales Bacilli Bacillota None Bacteria

Properties Information

Molecule Weight: 1270.4999999999998

TPSA？: 414.6399999999998

MolLogP？: -0.3875000000000179

Number of H-Donors: 13

Number of H-Acceptors: 14

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii MIC 10000.0 nM 10.1016/j.ejmech.2021.113488
Bacillus cereus Bacillus cereus MIC 16.0 ug.mL-1 10.1016/j.bmc.2007.08.007
Bacillus subtilis Bacillus subtilis MIC 1.0 ug.mL-1 10.1021/jm070282e
Bacillus subtilis Bacillus subtilis MIC 8.3 ug.mL-1 10.1021/jm0341352
Bacillus subtilis Bacillus subtilis MIC 16.0 ug.mL-1 10.1016/j.bmc.2007.08.007
Bacillus subtilis Bacillus subtilis MIC 20.0 ug.mL-1 10.1021/jm801577r
Bacillus subtilis Bacillus subtilis MIC 31.0 ug.mL-1 10.1021/jm801577r
Bacillus subtilis Bacillus subtilis Ratio 1.0 None 10.1021/jm0341352
Bacteria Cell membrane Activity nan None 10.1016/j.ejmech.2021.113488
Bacteria Lipopolysaccharide (LPS) Activity nan None 10.1016/j.ejmech.2021.113488
Candida albicans Candida albicans MIC 390.0 nM 10.1021/acs.jmedchem.7b00953
Candida albicans Candida albicans MIC 780.0 nM 10.1021/acs.jmedchem.7b00953
Candida albicans Candida albicans MIC 3125.0 nM 10.1021/acs.jmedchem.7b00953
Enterococcus faecalis Enterococcus faecalis MIC 1.0 ug.mL-1 10.1021/jm070282e
Enterococcus faecalis Enterococcus faecalis MIC 16.0 ug.mL-1 10.1016/j.bmc.2007.08.007
Enterococcus faecalis Enterococcus faecalis MIC 2500.0 nM 10.1016/j.ejmech.2021.113488
Escherichia coli Escherichia coli Activity 50.0 % 10.1016/j.bmc.2009.06.029
Escherichia coli Escherichia coli Activity nan None 10.1016/j.ejmech.2021.113488
Escherichia coli Escherichia coli MIC 8.0 ug.mL-1 10.1021/jm070282e
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1016/j.bmc.2007.08.007
Escherichia coli Escherichia coli MIC 20000.0 nM 10.1016/j.ejmech.2021.113488
Escherichia coli Escherichia coli MIC 25000.0 nM 10.1021/acs.jmedchem.7b00953
Homo sapiens L02 Activity nan None 10.1016/j.ejmech.2021.113488
Listeria monocytogenes Listeria monocytogenes Activity 1.62 % 10.1016/j.bmc.2009.06.029
Listeria monocytogenes Listeria monocytogenes Activity 59.0 % 10.1016/j.bmc.2009.06.029
Listeria monocytogenes Listeria monocytogenes IC50 9900.0 nM 10.1016/j.bmc.2009.06.029
Listeria monocytogenes Listeria monocytogenes IC50 13000.0 nM 10.1016/j.bmc.2009.06.029
Listeria monocytogenes Listeria monocytogenes ICmax 16.0 uM 10.1016/j.bmc.2009.06.029
Listeria monocytogenes Listeria monocytogenes ICmax 25.0 uM 10.1016/j.bmc.2009.06.029
Listeria monocytogenes Listeria monocytogenes T1/2 0.5383 hr 10.1016/j.bmc.2009.06.029
Micrococcus luteus Micrococcus luteus IC50 22000.0 nM 10.1016/j.bmc.2009.06.029
Micrococcus luteus Micrococcus luteus ICmax 70.0 uM 10.1016/j.bmc.2009.06.029
Pseudomonas aeruginosa Pseudomonas aeruginosa Activity nan None 10.1021/acs.jmedchem.7b00953
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 80000.0 nM 10.1016/j.ejmech.2021.113488
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 100000.0 nM 10.1021/acs.jmedchem.7b00953
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1016/j.ejmech.2021.113488
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/acs.jmedchem.7b00953
Staphylococcus aureus Staphylococcus aureus MIC 32.0 ug.mL-1 10.1016/j.bmc.2007.08.007
Staphylococcus aureus Staphylococcus aureus MIC 1560.0 nM 10.1021/acs.jmedchem.7b00953
Staphylococcus aureus Staphylococcus aureus MIC 2500.0 nM 10.1016/j.ejmech.2021.113488
Staphylococcus aureus Staphylococcus aureus MIC 20000.0 nM 10.1016/j.ejmech.2021.113488
Staphylococcus epidermidis Staphylococcus epidermidis MIC 1.0 ug.mL-1 10.1021/jm070282e
Staphylococcus epidermidis Staphylococcus epidermidis MIC 16.0 ug.mL-1 10.1016/j.bmc.2007.08.007
None ADMET Activity 2.0 ug ml-1 10.1021/jm070282e
None Erythrocyte HC50 14.0 uM 10.1016/j.ejmech.2021.113488
None Lipid bilayer Activity nan None 10.1016/j.ejmech.2021.113488
None Unchecked MHC 8.2 ug ml-1 10.1021/jm0341352
None Unchecked Ratio 2.0 ug ml-1 10.1021/jm070282e

Metabolism Information