(Oxacillin methyl ester)3,3-Dimethyl-6-[(5-methyl-3-phenyl-isoxazole-4-carbonyl)-amino]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

ID: ALA281444

Chembl Id: CHEMBL281444

PubChem CID: 23278033

Max Phase: Preclinical

Molecular Formula: C20H21N3O5S

Molecular Weight: 415.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)c3c(-c4ccccc4)noc3C)[C@H]2SC1(C)C

Standard InChI:  InChI=1S/C20H21N3O5S/c1-10-12(13(22-28-10)11-8-6-5-7-9-11)16(24)21-14-17(25)23-15(19(26)27-4)20(2,3)29-18(14)23/h5-9,14-15,18H,1-4H3,(H,21,24)/t14-,15+,18-/m1/s1

Standard InChI Key:  OUIFFUJXNMDTRR-RVKKMQEKSA-N

Alternative Forms

1. Parent:

   

   ALA281444

   Oxacillin methyl ester

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: 415.47

Molecular Weight (Monoisotopic): 415.1202

AlogP: 1.98

#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: 13.58

CX Basic pKa: ┄

CX LogP: 1.84

CX LogD: 1.84

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -0.27

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