3-Acetoxymethyl-7-(3H-imidazo[4,5-c]pyridin-2-ylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

ID: ALA13672

Chembl Id: CHEMBL13672

PubChem CID: 14891912

Max Phase: Preclinical

Molecular Formula: C20H23N5O5S

Molecular Weight: 445.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)OC(C)(C)C)N2C(=O)[C@@H](Nc3nc4cc[nH]cc-4n3)C2SC1

Standard InChI:  InChI=1S/C20H23N5O5S/c1-10(26)29-8-11-9-31-17-14(24-19-22-12-5-6-21-7-13(12)23-19)16(27)25(17)15(11)18(28)30-20(2,3)4/h5-7,14,17,21H,8-9H2,1-4H3,(H,23,24)/t14-,17?/m1/s1

Standard InChI Key:  POOWHGKVFBJMPX-XPCCGILXSA-N

Alternative Forms

1. Parent:

   

   ALA13672

   tert-butyl (7R)-3-(acetyloxymethyl)-7-(3H-imidazo[4,5-c]pyridin-2-ylamino)-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: 445.50

Molecular Weight (Monoisotopic): 445.1420

AlogP: 1.76

#Rotatable Bonds: 5

Polar Surface Area: 126.51

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.26

CX Basic pKa: 3.18

CX LogP: 1.55

CX LogD: 1.55

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -0.07

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