colistin   Click here for help

GtoPdb Ligand ID: 10794

Synonyms: Colobreathe® | polymyxin E | Promixin®
Approved drug
colistin is an approved drug (UK (2006))
Comment: Colistin is a cyclic polypeptide (IUPAC condensed sequence Unk-Dab-Thr-Dab-Dab(1)-Dab-D-Leu-Leu-Dab-Dab-Thr-(1)) antibiotic from Bacillus colistinus. It contains Polymyxins E1 and E2 and acts as a detergent on cell membranes.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 29
Hydrogen bond donors 18
Rotatable bonds 32
Topological polar surface area 490.66
Molecular weight 1154.75
XLogP 0.63
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES 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)CCCC(CC)C)CCN
Isomeric SMILES 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)CCCC(CC)C)CCN
InChI InChI=1S/C52H98N16O13/c1-9-29(6)11-10-12-40(71)59-32(13-19-53)47(76)68-42(31(8)70)52(81)64-35(16-22-56)44(73)63-37-18-24-58-51(80)41(30(7)69)67-48(77)36(17-23-57)61-43(72)33(14-20-54)62-49(78)38(25-27(2)3)66-50(79)39(26-28(4)5)65-45(74)34(15-21-55)60-46(37)75/h27-39,41-42,69-70H,9-26,53-57H2,1-8H3,(H,58,80)(H,59,71)(H,60,75)(H,61,72)(H,62,78)(H,63,73)(H,64,81)(H,65,74)(H,66,79)(H,67,77)(H,68,76)/t29?,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,41+,42+/m1/s1
InChI Key YKQOSKADJPQZHB-QNPLFGSASA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (UK (2006))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,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-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-5-methylheptanamide
International Nonproprietary Names Click here for help
INN number INN
916 colistin
Synonyms Click here for help
Colobreathe® | polymyxin E | Promixin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1267
Other databases
ChEMBL Ligand CHEMBL499783
GtoPdb PubChem SID 405560235
PubChem CID 5311054
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