quinupristin   Click here for help

GtoPdb Ligand ID: 10798

Synonyms: RP 57669 | RP-57669 | RP57669 | Synercid® (dalfopristin + quinupristin)
Approved drug
quinupristin is an approved drug (FDA (1999))
Compound class: Synthetic organic
Comment: Quinupristin is a semi-synthetic derivative of streptogramin B. It inhibits the late stage of protein synthesis by binding to the bacterial 50S ribosomal subunit.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 256.5
Molecular weight 1021.47
XLogP 3.79
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](N(C(=O)[C@H]3N(C1=O)CCC3)C)Cc1ccc(cc1)N(C)C)C[C@@H](CS[C@@H]1CN3CCC1CC3)C(=O)C2)c1ccccc1
Isomeric SMILES CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](N(C(=O)[C@H]3N(C1=O)CCC3)C)Cc1ccc(cc1)N(C)C)C[C@@H](CS[C@@H]1CN3CCC1CC3)C(=O)C2)c1ccccc1
InChI InChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35+,37-,38+,39+,40+,43-,44+,45+/m1/s1
InChI Key WTHRRGMBUAHGNI-LCYNINFDSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1999))
IUPAC Name Click here for help
N-[(3S,6S,12R,15S,16R,19S,22S,25R)-25-[[(3S)-1-azabicyclo[2.2.2]octan-3-yl]sulfanylmethyl]-3-[[4-(dimethylamino)phenyl]methyl]-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
6582 quinupristin
Synonyms Click here for help
RP 57669 | RP-57669 | RP57669 | Synercid® (dalfopristin + quinupristin)
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1499
Other databases
CAS Registry No. 120138-50-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL1200649
GtoPdb PubChem SID 405560239
PubChem CID 5388937
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