pirbenicillin   Click here for help

GtoPdb Ligand ID: 10845

Synonyms: CP-33,994 | CP-33,994-2
Compound class: Synthetic organic
Comment: Pirbenicillin is a semisynthetic penicillin with antibacterial activity against Gram-positive and Gram-negative bacteria [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 10
Topological polar surface area 192.38
Molecular weight 510.17
XLogP -2.16
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C(N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)c1ccccc1)CN=C(c1ccncc1)N
Isomeric SMILES O=C(N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)c1ccccc1)CN=C(c1ccncc1)N
InChI InChI=1S/C24H26N6O5S/c1-24(2)18(23(34)35)30-21(33)17(22(30)36-24)29-20(32)16(13-6-4-3-5-7-13)28-15(31)12-27-19(25)14-8-10-26-11-9-14/h3-11,16-18,22H,12H2,1-2H3,(H2,25,27)(H,28,31)(H,29,32)(H,34,35)/t16-,17-,18+,22-/m1/s1
InChI Key WRFCGBVLTRJBKN-QSNWEANLSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2S,5R,6R)-6-[[(2R)-2-[[2-[[amino(pyridin-4-yl)methylidene]amino]acetyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3937 pirbenicillin
Synonyms Click here for help
CP-33,994 | CP-33,994-2
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1048
Other databases
CAS Registry No. 55975-92-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL2110979
GtoPdb PubChem SID 405560286
PubChem CID 9871712
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