2-amino-N-(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-heptaazacyclotricosan-21-yl]carbamoyl}propyl)-3-hydroxybutanamide

• ChemBase ID: 133245
• Molecular Formular: C43H74N14O11
• Molecular Mass: 963.13486
• Monoisotopic Mass: 962.56614926
• SMILES: CC(C)CC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCC(C(=O)NC(C(=O)NC(C(=O)N1)Cc1ccccc1)CCN)NC(=O)C(CCN)NC(=O)C(C(C)O)N)C(C)O)CCN)CCN
• Canonical SMILES: NCCC(C(=O)NC1CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)Cc1ccccc1)CC(C)C)CCN)C(O)C)NC(=O)C(C(O)C)N
• InChI: InChI=1S/C43H74N14O11/c1-22(2)20-31-40(65)52-26(10-15-44)35(60)51-29(13-18-47)39(64)57-34(24(4)59)43(68)49-19-14-30(53-36(61)28(12-17-46)54-42(67)33(48)23(3)58)38(63)50-27(11-16-45)37(62)56-32(41(66)55-31)21-25-8-6-5-7-9-25/h5-9,22-24,26-34,58-59H,10-21,44-48H2,1-4H3,(H,49,68)(H,50,63)(H,51,60)(H,52,65)(H,53,61)(H,54,67)(H,55,66)(H,56,62)(H,57,64)
• InChIKey: PYHYGIPVYYRJHU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N-(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-heptaazacyclotricosan-21-yl]carbamoyl}propyl)-3-hydroxybutanamide
• IUPAC Traditional name: 2-amino-N-(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-heptaazacyclotricosan-21-yl]carbamoyl}propyl)-3-hydroxybutanamide
• Synonyms: PMBN; Polymyxin B nonapeptide hydrochloride

Database IDs

• MDL Number: MFCD00214217
• PubChem SID: 162227522; 24898270
• PubChem CID: 3344039

CALCULATED PROPERTIES

• Polarizability: 97.70617 Å^3
• Polar Surface Area: 432.46 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false
• Acid pKa: 11.622481
• H Acceptors: 16
• H Donor: 16
• LogD (pH = 5.5): -22.693283
• LogD (pH = 7.4): -17.448698
• Log P: -8.648065
• Molar Refractivity: 246.2272 cm^3

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - P2076

Biochem/physiol Actions
Polymyxin B nonapeptide (PMBN), a cationic cyclic peptide derived from the antibacterial peptide polymyxin B, specifically increases the permeability of the outer membrane of Gram-negative bacteria toward hydrophobic antibiotics.1,2,3 PMBN has been used to evaluate multidrug efflux inhibitors in E. coli.4
Polymyxin B nonapeptide hydrochloride is a derivative of PMB that induces outer membrane permeability in gram-negative bacteria.