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

ID: ALA13156

Chembl Id: CHEMBL13156

PubChem CID: 14891892

Max Phase: Preclinical

Molecular Formula: C30H26N8O3S2

Molecular Weight: 610.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](Nc3nc4ccccc4[nH]3)C2SC1

Standard InChI:  InChI=1S/C30H26N8O3S2/c1-37-30(34-35-36-37)43-17-20-16-42-27-23(33-29-31-21-14-8-9-15-22(21)32-29)26(39)38(27)24(20)28(40)41-25(18-10-4-2-5-11-18)19-12-6-3-7-13-19/h2-15,23,25,27H,16-17H2,1H3,(H2,31,32,33)/t23-,27?/m1/s1

Standard InChI Key:  LVSFSGVCCJHNTB-BRIWLPCBSA-N

Alternative Forms

1. Parent:

   

   ALA13156

   benzhydryl (7R)-7-(1H-benzimidazol-2-ylamino)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-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: 610.73

Molecular Weight (Monoisotopic): 610.1569

AlogP: 4.16

#Rotatable Bonds: 9

Polar Surface Area: 130.92

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.92

CX Basic pKa: 6.88

CX LogP: 5.02

CX LogD: 4.91

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.14

Np Likeness Score: -1.09

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