lenapenem   Click here for help

GtoPdb Ligand ID: 10825

Synonyms: BO-2727 | BO2727 | L-739,428 | L-739428
Compound class: Synthetic organic
Comment: Lenapenem (BO-2727) is a parenteral carbapenem class antibiotic [1,3]. It is active against methicillin-resistant staphylococci and has antipseudomonal activity [2].
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 147.43
Molecular weight 399.18
XLogP -0.86
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CNCC[C@H]([C@H]1NC[C@H](C1)SC1=C(C(=O)O)N2[C@H]([C@H]1C)[C@H](C2=O)[C@H](O)C)O
Isomeric SMILES CNCC[C@H]([C@H]1NC[C@H](C1)SC1=C(C(=O)O)N2[C@H]([C@H]1C)[C@H](C2=O)[C@H](O)C)O
InChI InChI=1S/C18H29N3O5S/c1-8-14-13(9(2)22)17(24)21(14)15(18(25)26)16(8)27-10-6-11(20-7-10)12(23)4-5-19-3/h8-14,19-20,22-23H,4-7H2,1-3H3,(H,25,26)/t8-,9-,10+,11+,12-,13-,14-/m1/s1
InChI Key PZLOCBSBEUDCPF-YJIVIRPOSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
7384 lenapenem
Synonyms Click here for help
BO-2727 | BO2727 | L-739,428 | L-739428
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 301
Other databases
CAS Registry No. 149951-16-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL3989459
GtoPdb PubChem SID 405560266
PubChem CID 216262
Search Google for chemical match using the InChIKey PZLOCBSBEUDCPF-YJIVIRPOSA-N
Search Google for chemicals with the same backbone PZLOCBSBEUDCPF
Search PubMed clinical trials lenapenem
Search PubMed titles lenapenem
Search PubMed titles/abstracts lenapenem
Search UniChem for chemical match using the InChIKey PZLOCBSBEUDCPF-YJIVIRPOSA-N
Search UniChem for chemicals with the same backbone PZLOCBSBEUDCPF