BRL-44154   Click here for help

GtoPdb Ligand ID: 11036

Synonyms: analogue 4f [Brown et al., 1991] [1] | BRL44154
Compound class: Synthetic organic
Comment: Strictly this is the parent molecule of BRL-44154 which referes to the sodium salt. BRL-44154 is a penicillin class antibiotic that was developed by SmithKline Beecham [2]. It has high stability to β-lactamases.
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 3
Rotatable bonds 7
Topological polar surface area 200.75
Molecular weight 467.13
XLogP -1.03
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES OC(=O)[C@@H]1N2C(=O)C[C@H]([C@H]2SC1(C)C)NC(=O)/C(=N/OC1CCCC1)/c1csc(n1)N
Isomeric SMILES OC(=O)[C@@H]1N2C(=O)C[C@H]([C@H]2SC1(C)C)NC(=O)/C(=N/OC1CCCC1)/c1csc(n1)N
InChI InChI=1S/C19H25N5O5S2/c1-19(2)14(17(27)28)24-12(25)7-10(16(24)31-19)21-15(26)13(11-8-30-18(20)22-11)23-29-9-5-3-4-6-9/h8-10,14,16H,3-7H2,1-2H3,(H2,20,22)(H,21,26)(H,27,28)/b23-13+/t10-,14+,16-/m1/s1
InChI Key KNTUUEGDGYZCIA-ZUPSXRMKSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3S,7R,7aR)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-cyclopentyloxyiminoacetyl]amino]-2,2-dimethyl-5-oxo-3,6,7,7a-tetrahydropyrrolo[2,1-b][1,3]thiazole-3-carboxylic acid
Synonyms Click here for help
analogue 4f [Brown et al., 1991] [1] | BRL44154
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 395
Other databases
GtoPdb PubChem SID 405560477
PubChem CID 126843198
Search Google for chemical match using the InChIKey KNTUUEGDGYZCIA-ZUPSXRMKSA-N
Search Google for chemicals with the same backbone KNTUUEGDGYZCIA
Search UniChem for chemical match using the InChIKey KNTUUEGDGYZCIA-ZUPSXRMKSA-N
Search UniChem for chemicals with the same backbone KNTUUEGDGYZCIA