1-Ethenyl-6,8-difluoro-7-(4-hydroxymethyl-piperidinyl)-4(1H)-oxoquinoline-3-carboxylic acid

ID: ALA1631376

PubChem CID: 50907732

Max Phase: Preclinical

Molecular Formula: C18H20F2N2O4

Molecular Weight: 366.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCC(CO)CC3)c(F)c21

Standard InChI:  InChI=1S/C18H20F2N2O4/c1-2-21-8-12(18(25)26)17(24)11-7-13(19)16(14(20)15(11)21)22-5-3-10(9-23)4-6-22/h7-8,10,23H,2-6,9H2,1H3,(H,25,26)

Standard InChI Key:  QNGDHYLAXURQET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   17.0652  -18.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0641  -19.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7789  -19.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7771  -17.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4925  -18.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4932  -19.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2085  -19.4383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9236  -19.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9188  -18.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2029  -17.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3507  -17.7918    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.3493  -19.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7808  -20.2694    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.1985  -16.9614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6307  -17.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3477  -18.1849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6257  -16.9517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2103  -20.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9256  -20.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6389  -19.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9262  -19.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9213  -20.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6353  -20.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3542  -20.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2049  -20.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4924  -20.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  3 13  1  0
  3  6  2  0
 10 14  2  0
  6  7  1  0
  9 15  1  0
  1  2  2  0
 15 16  1  0
  7  8  1  0
 15 17  2  0
  5  4  2  0
  7 18  1  0
  8  9  2  0
 18 19  1  0
 12 20  1  0
  4  1  1  0
  9 10  1  0
 10  5  1  0
  1 11  1  0
 12 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  2  3  1  0
 22 25  1  0
  2 12  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1631376

   1-Ethyl-6,8-difluoro-7-[4-(hydroxymethyl)piperidin-1-yl]-4-oxoquinoline-3-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: 366.36

Molecular Weight (Monoisotopic): 366.1391

AlogP: 2.21

#Rotatable Bonds: 4

Polar Surface Area: 82.77

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.76

CX Basic pKa: ┄

CX LogP: 1.90

CX LogD: 0.25

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.87

Np Likeness Score: -0.59

References

1. Srinivasan S, Beema Shafreen RM, Nithyanand P, Manisankar P, Pandian SK..  (2010)  Synthesis and in vitro antimicrobial evaluation of novel fluoroquinolone derivatives.,  45  (12): [PMID:20933306] [10.1016/j.ejmech.2010.09.036]

Source

Source(1):

• Scientific Literature