Sodium salt 3-[6,8-difluoro-1-(2-fluoro-ethyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carbonyloxymethyl]-6-(1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

ID: ALA55025

PubChem CID: 23695897

Max Phase: Preclinical

Molecular Formula: C26H26F3N4NaO7S

Molecular Weight: 596.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(COC(=O)c3cn(CCF)c4c(F)c(N5CCN(C)CC5)c(F)cc4c3=O)S[C@H]12.[Na+]

Standard InChI:  InChI=1S/C26H27F3N4O7S.Na/c1-12(34)17-23(36)33-21(25(37)38)16(41-24(17)33)11-40-26(39)14-10-32(4-3-27)19-13(22(14)35)9-15(28)20(18(19)29)31-7-5-30(2)6-8-31;/h9-10,12,17,24,34H,3-8,11H2,1-2H3,(H,37,38);/q;+1/p-1/t12-,17+,24-;/m1./s1

Standard InChI Key:  UCDKKMKMEFZMSH-KHIAQWRWSA-M

Molfile:  

     RDKit          2D

 44 47  0  0  0  0  0  0  0  0999 V2000
    2.4042   -7.0125    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    1.4292   -4.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -3.2917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -1.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1875    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7542   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750    2.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -4.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -3.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -5.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250    1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -5.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500   -0.4042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792    1.0375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750    1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417    2.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -2.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -1.1375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917    3.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2662   -4.0540    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632   -2.5674    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  2  1  0
  6 20  1  0
  7  3  2  0
  8 13  1  0
  4  9  1  0
 10  5  1  0
 11 15  1  0
 12 11  1  0
 13  6  1  0
 14 12  1  0
 15  6  2  0
 16 14  2  0
 17 18  2  0
 18  8  1  0
 19 16  1  0
 20 25  1  0
 21  3  1  0
 22  7  1  0
 23 35  1  0
 24  5  2  0
 25 22  1  0
 26 13  2  0
 27 21  1  0
 10 28  1  0
 29 19  1  0
 30 19  1  0
 31 20  2  0
 32 21  2  0
 33 14  1  0
 34 17  1  0
 35 30  1  0
 36 29  1  0
 37 11  1  0
 28 38  1  1
 39 41  1  0
 40 23  1  0
 41 37  1  0
 42 28  1  0
  4 10  1  0
  7  9  1  0
  8 12  2  0
 17 16  1  0
 36 23  1  0
 10 43  1  1
  4 44  1  6
M  CHG  2   1   1  27  -1
M  END

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: 596.58

Molecular Weight (Monoisotopic): 596.1553

AlogP: 1.37

#Rotatable Bonds: 8

Polar Surface Area: 132.62

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.16

CX Basic pKa: 5.81

CX LogP: -1.60

CX LogD: -2.56

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.34

Np Likeness Score: -0.38

References

1. Corraz AJ, Dax SL, Dunlap NK, Georgopapadakou NH, Keith DD, Pruess DL, Rossman PL, Then R, Unowsky J, Wei CC..  (1992)  Dual-action penems and carbapenems.,  35  (10): [PMID:1588561] [10.1021/jm00088a019]

Source

Source(1):

• Scientific Literature