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

ID: ALA13731

Chembl Id: CHEMBL13731

PubChem CID: 14891949

Max Phase: Preclinical

Molecular Formula: C30H28N4O5S

Molecular Weight: 556.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC3=NC(c4ccc(O)c(O)c4)CN3)C2SC1

Standard InChI:  InChI=1S/C30H28N4O5S/c1-17-16-40-28-24(33-30-31-15-21(32-30)20-12-13-22(35)23(36)14-20)27(37)34(28)25(17)29(38)39-26(18-8-4-2-5-9-18)19-10-6-3-7-11-19/h2-14,21,24,26,28,35-36H,15-16H2,1H3,(H2,31,32,33)/t21?,24-,28?/m1/s1

Standard InChI Key:  UAGOGPWJQCPPAI-MKNZIIIOSA-N

Alternative Forms

1. Parent:

   

   ALA13731

   benzhydryl (7R)-7-[[5-(3,4-dihydroxyphenyl)-4,5-dihydro-1H-imidazol-2-yl]amino]-3-methyl-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: 556.64

Molecular Weight (Monoisotopic): 556.1780

AlogP: 3.58

#Rotatable Bonds: 6

Polar Surface Area: 123.49

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.67

CX Basic pKa: 8.94

CX LogP: 3.87

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: 0.29

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