Sodium salt 3-[4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinolin-7-yl)-piperazine-1-carbonyloxymethyl]-6-(1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

ID: ALA300530

PubChem CID: 23695898

Max Phase: Preclinical

Molecular Formula: C27H26FN4NaO9S

Molecular Weight: 602.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(COC(=O)N3CCN(c4cc5c(cc4F)c(=O)c(C(=O)O)cn5C4CC4)CC3)S[C@H]12.[Na+]

Standard InChI:  InChI=1S/C27H27FN4O9S.Na/c1-12(33)20-23(35)32-21(26(38)39)19(42-24(20)32)11-41-27(40)30-6-4-29(5-7-30)18-9-17-14(8-16(18)28)22(34)15(25(36)37)10-31(17)13-2-3-13;/h8-10,12-13,20,24,33H,2-7,11H2,1H3,(H,36,37)(H,38,39);/q;+1/p-1/t12-,20+,24-;/m1./s1

Standard InChI Key:  CTPINBXEXWJVAL-VSJXDHADSA-M

Molfile:  

     RDKit          2D

 45 49  0  0  0  0  0  0  0  0999 V2000
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    6.1042   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6125  -12.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -7.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -7.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167  -12.1875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875  -12.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250   -7.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8917   -9.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -5.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -9.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -6.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375  -12.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708  -13.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6625  -10.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042  -11.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125  -10.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -9.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875  -12.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292  -14.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083  -12.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042  -14.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3417   -5.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -9.8542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -4.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083  -11.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208  -12.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547  -12.9479    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757  -11.4632    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 13  1  0
  7 10  1  0
  8  3  2  0
  9 21  1  0
 10 15  1  0
  4 11  1  0
 12  5  1  0
 13  9  1  0
 14  7  1  0
 15 16  2  0
 16 22  1  0
 17 29  1  0
 18 17  1  0
 19  7  1  0
 20  3  1  0
 21 24  2  0
 22 33  1  0
 23  6  1  0
 24 16  1  0
 25 19  1  0
 26 19  1  0
 27  8  1  0
 28  5  2  0
 29 27  1  0
 30 13  2  0
 31 18  1  0
 32 18  1  0
 33 32  1  0
 34 31  1  0
 35 17  2  0
 36 20  1  0
 12 37  1  0
 38 20  2  0
 39 23  2  0
 40 24  1  0
 41 23  1  0
 37 42  1  1
 43 37  1  0
  4 12  1  0
  8 11  1  0
 22 34  1  0
 10  9  2  0
  6 14  2  0
 26 25  1  0
 12 44  1  1
  4 45  1  6
M  CHG  2   1   1  36  -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: 602.60

Molecular Weight (Monoisotopic): 602.1483

AlogP: 1.64

#Rotatable Bonds: 7

Polar Surface Area: 169.92

Molecular Species: ACID

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.93

CX Basic pKa: ┄

CX LogP: 0.44

CX LogD: -4.30

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.39

Np Likeness Score: -0.45

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