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

ID: ALA13758

Chembl Id: CHEMBL13758

PubChem CID: 14891914

Max Phase: Preclinical

Molecular Formula: C21H25N5O5S

Molecular Weight: 459.53

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H25N5O5S/c1-10(27)30-8-11-9-32-18-15(17(28)26(18)16(11)19(29)31-21(2,3)4)25-20-23-13-6-5-12(22)7-14(13)24-20/h5-7,15,18H,8-9,22H2,1-4H3,(H2,23,24,25)/t15-,18?/m1/s1

Standard InChI Key:  QMBIMRKFPGPMOC-NNJIEVJOSA-N

Alternative Forms

1. Parent:

   

   ALA13758

   tert-butyl (7R)-3-(acetyloxymethyl)-7-[(6-amino-1H-benzimidazol-2-yl)amino]-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: 459.53

Molecular Weight (Monoisotopic): 459.1576

AlogP: 2.00

#Rotatable Bonds: 5

Polar Surface Area: 139.64

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.10

CX Basic pKa: 8.40

CX LogP: 1.10

CX LogD: 0.19

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -0.14

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