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8068-28-8 molecular structure
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pentasodium N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9R,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(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 pentamethanesulfonate

ChemBase ID: 133758
Molecular Formular: C58H115N16Na5O28S5
Molecular Mass: 1759.89795
Monoisotopic Mass: 1758.61587353
SMILES and InChIs

SMILES:
CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CCN)CC(C)C)CC(C)C)CCN)CCN)[C@@H](C)O.CS(=O)(=O)[O-].CS(=O)(=O)[O-].CS(=O)(=O)[O-].CS(=O)(=O)[O-].CS(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+]
Canonical SMILES:
[O-]S(=O)(=O)C.[O-]S(=O)(=O)C.[O-]S(=O)(=O)C.[O-]S(=O)(=O)C.[O-]S(=O)(=O)C.NCC[C@@H](C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CCN)CC(C)C)CC(C)C)CCN)[C@H](O)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)CCCCC(CC)C)CCN.[Na+].[Na+].[Na+].[Na+].[Na+]
InChI:
InChI=1S/C53H100N16O13.5CH4O3S.5Na/c1-9-30(6)12-10-11-13-41(72)60-33(14-20-54)48(77)69-43(32(8)71)53(82)65-36(17-23-57)45(74)64-38-19-25-59-52(81)42(31(7)70)68-49(78)37(18-24-58)62-44(73)34(15-21-55)63-50(79)39(26-28(2)3)67-51(80)40(27-29(4)5)66-46(75)35(16-22-56)61-47(38)76;5*1-5(2,3)4;;;;;/h28-40,42-43,70-71H,9-27,54-58H2,1-8H3,(H,59,81)(H,60,72)(H,61,76)(H,62,73)(H,63,79)(H,64,74)(H,65,82)(H,66,75)(H,67,80)(H,68,78)(H,69,77);5*1H3,(H,2,3,4);;;;;/q;;;;;;5*+1/p-5/t30?,31-,32-,33+,34-,35+,36+,37+,38+,39+,40-,42+,43+;;;;;;;;;;/m1........../s1
InChIKey:
WSDSONZFNWDYGZ-BKFDUBCBSA-I

Cite this record

CBID:133758 http://www.chembase.cn/molecule-133758.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
pentasodium N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9R,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(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 pentamethanesulfonate
IUPAC Traditional name
pentasodium N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9R,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(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 pentamesylate
Synonyms
Colimycin sodium methanesulfonate
Methanesulfonic acid derivative of Polymyxin E
Polymyxin E sodium methanesulfonate
Colistin sodium methanesulfonate
CAS Number
8068-28-8
EC Number
232-516-9
MDL Number
MFCD00130824
PubChem SID
162228035
24892418
PubChem CID
16211791

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
C1511 external link Add to cart Please log in.
Data Source Data ID
PubChem 16211791 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.570662  H Acceptors 18 
H Donor 18  LogD (pH = 5.5) -22.614998 
LogD (pH = 7.4) -18.120953  Log P -7.6513867 
Molar Refractivity 302.2701 cm3 Polarizability 120.02434 Å3
Polar Surface Area 490.66 Å2 Rotatable Bonds 29 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Bioassay(PubChem)
RTECS
GH1650000 expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - C1511 external link
Biochem/physiol Actions
Mode of Action: Binds to lipids on the cell cytoplasmic membrane of Gram-negative bacteria and disrupts the cell wall integrity.Antimicrobial spectrum: Gram-negative bacteria.
Cyclopolypeptide antibiotic. Endotoxin-binding capacity3 Colistin′s activity stems from the hydrophobic and hydrophillic regions. They solubilze the cytoplasmic membrane which contributes to the bactericidal effect 4.
Application
Colistin sodium methanesulfate is used to permeabilize bacterial cell membranes and to study mannose-resistant haemagglutination. It is used to study effective treatments of P. aeruginosa infections in cystic fibrosis patients 1 and to study the pharmacokinetics and BAL concentration of colistin in critically ill patients 2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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