(6S)-N-(3-amino-1-{[(2R)-1-[(3-amino-1-{[(18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl)carbamoyl]-2-hydroxypropyl]carbamoyl}propyl)-6-methyloctanamide

• ChemBase ID: 176834
• Molecular Formular: C56H98N16O13
• Molecular Mass: 1203.47672
• Monoisotopic Mass: 1202.74992728
• SMILES: C1(=O)N[C@@H](C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC[C@@H]1NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CCCC[C@H](CC)C)CCN)[C@H](O)C)CCN)[C@H](O)C)CCN)CCN)CC(C)C)Cc1ccccc1)CCN
• Canonical SMILES: NCCC(C(=O)N[C@H]1CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)[C@H](NC1=O)CCN)Cc1ccccc1)CC(C)C)CCN)[C@H](O)C)NC(=O)C([C@H](O)C)NC(=O)C(NC(=O)CCCC[C@H](CC)C)CCN
• InChI: InChI=1S/C56H98N16O13/c1-7-32(4)13-11-12-16-44(75)63-36(17-23-57)51(80)72-46(34(6)74)56(85)68-39(20-26-60)48(77)67-41-22-28-62-55(84)45(33(5)73)71-52(81)40(21-27-61)65-47(76)37(18-24-58)66-53(82)42(29-31(2)3)69-54(83)43(30-35-14-9-8-10-15-35)70-49(78)38(19-25-59)64-50(41)79/h8-10,14-15,31-34,36-43,45-46,73-74H,7,11-13,16-30,57-61H2,1-6H3,(H,62,84)(H,63,75)(H,64,79)(H,65,76)(H,66,82)(H,67,77)(H,68,85)(H,69,83)(H,70,78)(H,71,81)(H,72,80)/t32-,33+,34+,36?,37?,38+,39?,40?,41-,42?,43?,45?,46?/m0/s1
• InChIKey: WQVJHHACXVLGBL-XUEDPNQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-N-(3-amino-1-{[(2R)-1-[(3-amino-1-{[(18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl)carbamoyl]-2-hydroxypropyl]carbamoyl}propyl)-6-methyloctanamide
• IUPAC Traditional name: (6S)-N-(3-amino-1-{[(2R)-1-[(3-amino-1-{[(18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl)carbamoyl]-2-hydroxypropyl]carbamoyl}propyl)-6-methyloctanamide
• Synonyms: N-[3-Amino-1-[[1-[[3-amino-1-[[6,9,18-tris(2-aminoethyl)-15-benzyl-3-(1-hydroxyethyl)-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]carbamoyl]propyl]carbamoyl]-2-hydroxy-propyl]carbamoyl]propyl]-6-methyl-octanamide Sulfuric Acid; Polymyxin B Sulfate

Database IDs

• CAS Number: 1405-20-5
• PubChem SID: 164232744
• PubChem CID: 71751723

CALCULATED PROPERTIES

• Acid pKa: 11.573131
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -22.212782
• LogD (pH = 7.4): -17.71875
• Log P: -7.249171
• Molar Refractivity: 313.2155 cm^3
• Polarizability: 124.05702 Å^3
• Polar Surface Area: 490.66 Å^2
• Rotatable Bonds: 29
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 217-220°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P689400

Antibiotic with bactericidal action on E. coli. Binds to the lipid A portion of bacterial lipopolysaccharides. Induces pore formation in the membranes of cortex cells from excised sorghum roots. Mixture of Polymyxin B1 and B2 sulfate.Biological potency (d

REFERENCES

• Coppi, G., et al.: J. Pharm. Pharmacol., 60, 21 (2008)
• Roche, S., et al.: Food Microbiol., 26, 21 (2008)
• Kawanishi, T., et al.: Plant Pathol., 58, 237 (2008)