colistin   

GtoPdb Ligand ID: 10794

Synonyms: Colobreathe® | polymyxin E | Promixin®
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
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
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
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
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
INN number INN
916 colistin
Synonyms
Colobreathe® | polymyxin E | Promixin®
Database Links
Specialist databases
AntibioticDB 1059
Other databases
ChEMBL Ligand CHEMBL499783
GtoPdb PubChem SID 405560235
PubChem CID 5311054
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