1-([1,1'-biphenyl]-4-ylmethyl)-7-((2-aminoethyl)amino)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA4474303

PubChem CID: 134603904

Max Phase: Preclinical

Molecular Formula: C25H22FN3O3

Molecular Weight: 431.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCCNc1cc2c(cc1F)c(=O)c(C(=O)O)cn2Cc1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C25H22FN3O3/c26-21-12-19-23(13-22(21)28-11-10-27)29(15-20(24(19)30)25(31)32)14-16-6-8-18(9-7-16)17-4-2-1-3-5-17/h1-9,12-13,15,28H,10-11,14,27H2,(H,31,32)

Standard InChI Key:  IEWWOOFEECNLNI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.7189   -9.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7178  -10.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4258  -10.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4240   -9.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1327   -9.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1315  -10.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8377  -10.8095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5496  -10.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5507   -9.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8400   -9.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8400   -8.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2594   -9.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9661   -9.5852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2614   -8.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8354  -11.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5420  -12.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5383  -12.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2441  -13.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9539  -12.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9536  -12.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2472  -11.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6592  -13.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6567  -14.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3630  -14.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0722  -14.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0708  -13.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3640  -12.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0111   -9.1750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097  -10.8110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024  -10.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5943  -10.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8869  -10.4007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 19 22  1  0
  1 28  1  0
  2 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474303

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 431.47

Molecular Weight (Monoisotopic): 431.1645

AlogP: 3.92

#Rotatable Bonds: 7

Polar Surface Area: 97.35

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.83

CX Basic pKa: 9.42

CX LogP: 1.30

CX LogD: 1.31

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.41

Np Likeness Score: -0.97

References

1. Delgado JL, Lentz SRC, Kulkarni CA, Chheda PR, Held HA, Hiasa H, Kerns RJ..  (2019)  Probing structural requirements for human topoisomerase I inhibition by a novel N1-Biphenyl fluoroquinolone.,  172  [PMID:30959322] [10.1016/j.ejmech.2019.03.040]

Source

Source(1):

• Scientific Literature