daptomycin   Click here for help

GtoPdb Ligand ID: 10904

Synonyms: Cubicin® | LY-146032 | LY146032
Approved drug
daptomycin is an approved drug (FDA (2003), EMA (2006))
Compound class: Synthetic organic
Comment: Daptomycin is a semi-synthetic cyclic lipopeptide antibiotic with broad-spectrum activity against Gram-positive bacteria. It is a bacterial metabolite that was isolated from Streptomyces roseosporus. Daptomycin rapidly depolarizes the bacterial cell membrane which disrupts DNA, RNA and protein synthesis and results in cell death.
IThis antibiotic was removed from the World Health Organization's List of Essential Medicines in 2019.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 42
Hydrogen bond donors 22
Rotatable bonds 39
Topological polar surface area 702.02
Molecular weight 1619.71
XLogP 1.92
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES NCCC[C@@H]1NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc2c[nH]c3c2cccc3)NC(=O)CCCCCCCCC)CC(=O)N)CC(=O)O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC(=O)O)C)CC(=O)O)CO)[C@@H](CC(=O)O)C)CC(=O)c1ccccc1N
Isomeric SMILES NCCC[C@@H]1NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc2c[nH]c3c2cccc3)NC(=O)CCCCCCCCC)CC(=O)N)CC(=O)O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC(=O)O)C)CC(=O)O)CO)[C@@H](CC(=O)O)C)CC(=O)c1ccccc1N
InChI InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49+,50-,60+,61+/m1/s1
InChI Key DOAKLVKFURWEDJ-RWDRXURGSA-N
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InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel