(Dicloxacillin methyl ester)6-{[3-(2,6-Dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

ID: ALA26227

Chembl Id: CHEMBL26227

PubChem CID: 44459462

Max Phase: Preclinical

Molecular Formula: C20H19Cl2N3O5S

Molecular Weight: 484.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)c3c(-c4c(Cl)cccc4Cl)noc3C)[C@H]2SC1(C)C

Standard InChI:  InChI=1S/C20H19Cl2N3O5S/c1-8-11(13(24-30-8)12-9(21)6-5-7-10(12)22)16(26)23-14-17(27)25-15(19(28)29-4)20(2,3)31-18(14)25/h5-7,14-15,18H,1-4H3,(H,23,26)/t14-,15+,18-/m1/s1

Standard InChI Key:  WVKBVTWOICKEKU-RVKKMQEKSA-N

Alternative Forms

1. Parent:

   

   ALA26227

   methyl (2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 484.36

Molecular Weight (Monoisotopic): 483.0422

AlogP: 3.29

#Rotatable Bonds: 4

Polar Surface Area: 101.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.57

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -0.41

References

1. Blanpain PC, Nagy JB, Laurent GH, Durant FV..  (1980)  A multifaceted approach to the study of the side-chain conformation in beta-lactamase-resistant penicillins.,  23  (12): [PMID:6969804] [10.1021/jm00186a002]

Source

Source(1):

• Scientific Literature