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

ID: ALA269426

Chembl Id: CHEMBL269426

PubChem CID: 14891882

Max Phase: Preclinical

Molecular Formula: C31H29N5O5S

Molecular Weight: 583.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](Nc3nc4cc(CN)ccc4[nH]3)C2SC1

Standard InChI:  InChI=1S/C31H29N5O5S/c1-18(37)40-16-22-17-42-29-25(35-31-33-23-13-12-19(15-32)14-24(23)34-31)28(38)36(29)26(22)30(39)41-27(20-8-4-2-5-9-20)21-10-6-3-7-11-21/h2-14,25,27,29H,15-17,32H2,1H3,(H2,33,34,35)/t25-,29?/m1/s1

Standard InChI Key:  RPZHMMFWENGRPE-MIJJZIGMSA-N

Alternative Forms

1. Parent:

   

   ALA269426

   benzhydryl (7R)-3-(acetyloxymethyl)-7-[[6-(aminomethyl)-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: 583.67

Molecular Weight (Monoisotopic): 583.1889

AlogP: 3.87

#Rotatable Bonds: 9

Polar Surface Area: 139.64

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.91

CX Basic pKa: 9.08

CX LogP: 3.51

CX LogD: 1.77

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: -0.13

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