3-Methyl-8-oxo-7-(4-phenyl-4,5-dihydro-1H-imidazol-2-ylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

ID: ALA276686

Chembl Id: CHEMBL276686

PubChem CID: 14891947

Max Phase: Preclinical

Molecular Formula: C30H28N4O3S

Molecular Weight: 524.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC3=NC(c4ccccc4)CN3)C2SC1

Standard InChI:  InChI=1S/C30H28N4O3S/c1-19-18-38-28-24(33-30-31-17-23(32-30)20-11-5-2-6-12-20)27(35)34(28)25(19)29(36)37-26(21-13-7-3-8-14-21)22-15-9-4-10-16-22/h2-16,23-24,26,28H,17-18H2,1H3,(H2,31,32,33)/t23?,24-,28?/m1/s1

Standard InChI Key:  OSFQBVXHSBFWEL-MWRHLSOJSA-N

Alternative Forms

1. Parent:

   

   ALA276686

   benzhydryl (7R)-3-methyl-8-oxo-7-[(5-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino]-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: 524.65

Molecular Weight (Monoisotopic): 524.1882

AlogP: 4.17

#Rotatable Bonds: 6

Polar Surface Area: 83.03

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.14

CX Basic pKa: 9.80

CX LogP: 4.96

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.37

Np Likeness Score: 0.04

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