3-Acetoxymethyl-7-(5-methyl-1H-benzoimidazol-2-ylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

ID: ALA275137

Chembl Id: CHEMBL275137

PubChem CID: 44268717

Max Phase: Preclinical

Molecular Formula: C31H28N4O5S

Molecular Weight: 568.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](Nc3nc4cc(C)ccc4[nH]3)C2SC1

Standard InChI:  InChI=1S/C31H28N4O5S/c1-18-13-14-23-24(15-18)33-31(32-23)34-25-28(37)35-26(22(16-39-19(2)36)17-41-29(25)35)30(38)40-27(20-9-5-3-6-10-20)21-11-7-4-8-12-21/h3-15,25,27,29H,16-17H2,1-2H3,(H2,32,33,34)/t25-,29?/m1/s1

Standard InChI Key:  CLBHBPHMHPTRIQ-MIJJZIGMSA-N

Alternative Forms

1. Parent:

   

   ALA275137

   benzhydryl (7R)-3-(acetyloxymethyl)-7-[(6-methyl-1H-benzimidazol-2-yl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-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: 568.66

Molecular Weight (Monoisotopic): 568.1780

AlogP: 4.72

#Rotatable Bonds: 8

Polar Surface Area: 113.62

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.00

CX Basic pKa: 7.31

CX LogP: 4.89

CX LogD: 4.65

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.23

Np Likeness Score: -0.25

References

1. Jung F, Delvare C, Boucherot D, Hamon A, Ackerley N, Betts MJ..  (1991)  Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.,  34  (3): [PMID:2002452] [10.1021/jm00107a035]

Source

Source(1):

• Scientific Literature