(R)-1-([1,1'-biphenyl]-4-ylmethyl)-7-(3-carbamoylpyrrolidin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4dihydroquinoline-3-carboxylic acid

ID: ALA4475343

PubChem CID: 134603935

Max Phase: Preclinical

Molecular Formula: C29H26FN3O5

Molecular Weight: 515.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(N2CC[C@@H](C(N)=O)C2)c(F)cc2c(=O)c(C(=O)O)cn(Cc3ccc(-c4ccccc4)cc3)c12

Standard InChI:  InChI=1S/C29H26FN3O5/c1-38-27-24-21(13-23(30)25(27)32-12-11-20(15-32)28(31)35)26(34)22(29(36)37)16-33(24)14-17-7-9-19(10-8-17)18-5-3-2-4-6-18/h2-10,13,16,20H,11-12,14-15H2,1H3,(H2,31,35)(H,36,37)/t20-/m1/s1

Standard InChI Key:  KKNRMJZKPRRTNJ-HXUWFJFHSA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
    4.0185   -9.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -9.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254  -10.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7236   -8.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4322   -9.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4311   -9.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1373  -10.2564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8492   -9.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -9.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1396   -8.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1396   -7.7980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5590   -8.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2657   -9.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5610   -7.8047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1350  -11.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8416  -11.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8379  -12.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5436  -12.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2535  -12.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2531  -11.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5468  -11.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9588  -12.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9563  -13.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6625  -13.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3718  -13.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3704  -12.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6635  -12.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271  -11.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202  -11.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093  -10.2579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3107   -8.6219    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -9.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143  -10.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4224  -11.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218  -11.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010  -10.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692   -9.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7193  -11.1084    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
  3 28  1  0
 28 29  1  0
  2 30  1  0
  1 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 30  1  0
 36 37  2  0
 36 38  1  0
 33 36  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4475343

   ---

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: 515.54

Molecular Weight (Monoisotopic): 515.1856

AlogP: 3.87

#Rotatable Bonds: 7

Polar Surface Area: 114.86

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.05

CX Basic pKa: ┄

CX LogP: 3.82

CX LogD: 2.45

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.39

Np Likeness Score: -0.79

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