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

ID: ALA269698

Chembl Id: CHEMBL269698

PubChem CID: 14891886

Max Phase: Preclinical

Molecular Formula: C31H25F3N4O5S

Molecular Weight: 622.63

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C31H25F3N4O5S/c1-17(39)42-15-20-16-44-28-24(37-30-35-22-13-12-21(31(32,33)34)14-23(22)36-30)27(40)38(28)25(20)29(41)43-26(18-8-4-2-5-9-18)19-10-6-3-7-11-19/h2-14,24,26,28H,15-16H2,1H3,(H2,35,36,37)/t24-,28?/m1/s1

Standard InChI Key:  JKJMTAOPHUTCNX-RIBGEGAISA-N

Alternative Forms

1. Parent:

   

   ALA269698

   benzhydryl (7R)-3-(acetyloxymethyl)-8-oxo-7-[[6-(trifluoromethyl)-1H-benzimidazol-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: 622.63

Molecular Weight (Monoisotopic): 622.1498

AlogP: 5.43

#Rotatable Bonds: 8

Polar Surface Area: 113.62

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.89

CX Basic pKa: 6.67

CX LogP: 5.26

CX LogD: 5.19

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.20

Np Likeness Score: -0.39

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