7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

ID: ALA13545

Chembl Id: CHEMBL13545

PubChem CID: 14891971

Max Phase: Preclinical

Molecular Formula: C18H24N6O3S3

Molecular Weight: 468.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nnc(SCC2=C(C(=O)OC(C)(C)C)N3C(=O)[C@@H](NC4=NCCN4)C3SC2)s1

Standard InChI:  InChI=1S/C18H24N6O3S3/c1-9-22-23-17(30-9)29-8-10-7-28-14-11(21-16-19-5-6-20-16)13(25)24(14)12(10)15(26)27-18(2,3)4/h11,14H,5-8H2,1-4H3,(H2,19,20,21)/t11-,14?/m1/s1

Standard InChI Key:  IZISUOOPUPOGCL-YNODCEANSA-N

Alternative Forms

1. Parent:

   

   ALA13545

   tert-butyl (7R)-7-(4,5-dihydro-1H-imidazol-2-ylamino)-3-[(5-methyl-1,3,4-thiadiazol-2-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: 468.63

Molecular Weight (Monoisotopic): 468.1072

AlogP: 1.37

#Rotatable Bonds: 5

Polar Surface Area: 108.81

Molecular Species: BASE

HBA: 11

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.14

CX Basic pKa: 9.74

CX LogP: 1.04

CX LogD: -1.04

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -0.86

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