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

ID: ALA275939

Chembl Id: CHEMBL275939

PubChem CID: 44268705

Max Phase: Preclinical

Molecular Formula: C30H26N4O6S

Molecular Weight: 570.63

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C30H26N4O6S/c1-17(35)39-15-20-16-41-28-24(33-30-31-22-13-12-21(36)14-23(22)32-30)27(37)34(28)25(20)29(38)40-26(18-8-4-2-5-9-18)19-10-6-3-7-11-19/h2-14,24,26,28,36H,15-16H2,1H3,(H2,31,32,33)/t24-,28?/m1/s1

Standard InChI Key:  DXVDQIBBHQOQGW-RIBGEGAISA-N

Alternative Forms

1. Parent:

   

   ALA275939

   benzhydryl (7R)-3-(acetyloxymethyl)-7-[(6-hydroxy-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: 570.63

Molecular Weight (Monoisotopic): 570.1573

AlogP: 4.11

#Rotatable Bonds: 8

Polar Surface Area: 133.85

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.15

CX Basic pKa: 7.36

CX LogP: 3.94

CX LogD: 3.78

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.21

Np Likeness Score: 0.05

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