3-Chloro-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ID: ALA292112

Chembl Id: CHEMBL292112

PubChem CID: 44303023

Max Phase: Preclinical

Molecular Formula: C13H11ClN2O4S2

Molecular Weight: 358.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1cccs1)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CS[C@H]12

Standard InChI:  InChI=1S/C13H11ClN2O4S2/c14-7-5-22-12-9(11(18)16(12)10(7)13(19)20)15-8(17)4-6-2-1-3-21-6/h1-3,9,12H,4-5H2,(H,15,17)(H,19,20)/t9-,12-/m1/s1

Standard InChI Key:  JOPWATABERKASH-BXKDBHETSA-N

Alternative Forms

1. Parent:

   

   ALA292112

   (6R,7R)-3-chloro-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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: 358.83

Molecular Weight (Monoisotopic): 357.9849

AlogP: 1.23

#Rotatable Bonds: 4

Polar Surface Area: 86.71

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.12

CX Basic pKa:

CX LogP: 0.69

CX LogD: -2.77

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -0.98

References

1. Kukolja S, Wright WE, Quay JF, Pfeil-Doyle J, Draheim SE, Eudaly JA, Johnson RJ, Ott JL, Counter FT, Cooper RD..  (1988)  Oral absorption of cephalosporin antibiotics. 1. Synthesis, biological properties, and oral bioavailability of 7-(arylacetamido)-3-chloro cephalosporins in animals.,  31  (10): [PMID:3172134] [10.1021/jm00118a022]

2. Indelicato JM, Dinner A, Peters LR, Wilham WL..  (1977)  Hydrolysis of 3-chloro-3-cephems. Intramolecular nucleophilic attack in cefaclor.,  20  (7): [PMID:874971] [10.1021/jm00217a021]

Source

Source(1):

• Scientific Literature