7-((R)-3-((S)-1-aminoethyl)pyrrolidin-1-yl)-6-chloro-5-cyclopropyl-8-fluoro-2-methyloxazolo[4,5-c]quinolin-4(5H)-one

ID: ALA4786331

PubChem CID: 162667088

Max Phase: Preclinical

Molecular Formula: C20H22ClFN4O2

Molecular Weight: 404.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc2c(=O)n(C3CC3)c3c(Cl)c(N4CC[C@@H]([C@H](C)N)C4)c(F)cc3c2o1

Standard InChI:  InChI=1S/C20H22ClFN4O2/c1-9(23)11-5-6-25(8-11)18-14(22)7-13-17(15(18)21)26(12-3-4-12)20(27)16-19(13)28-10(2)24-16/h7,9,11-12H,3-6,8,23H2,1-2H3/t9-,11+/m0/s1

Standard InChI Key:  LOCSNCVSEDLFDP-GXSJLCMTSA-N

Molfile:  

 
     RDKit          2D

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   26.2796  -18.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9877  -18.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9859  -16.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6945  -17.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6979  -18.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4063  -18.5194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1160  -18.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3996  -16.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1110  -17.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7162  -16.7318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3787  -15.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5651  -16.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7831  -15.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8251  -18.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4085  -19.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0028  -20.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8200  -20.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5730  -16.8888    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.5720  -18.5220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9882  -19.3429    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.8306  -18.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4864  -19.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6882  -19.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2859  -18.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4735  -18.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9907  -19.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1438  -17.9607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2805  -17.9782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8 15  2  0
  7 16  1  0
 17 16  1  0
 18 17  1  0
 16 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
 20 22  1  0
 22 25  1  0
 24 23  1  0
 23 20  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  6
 25 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4786331

   ---

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: 404.87

Molecular Weight (Monoisotopic): 404.1415

AlogP: 3.75

#Rotatable Bonds: 3

Polar Surface Area: 77.29

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.07

CX LogP: 1.98

CX LogD: -0.53

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: -0.66

References

1. Kirk, R., Ratcliffe, A., Noonan, G., Uosis-Martin, M., Lyth, D., Bardell-Cox, O., Massam, J., Schofield, P., Lyons, A., Clare, D., Maclean, J., Smith, A., Savage, V., Mohmed, S., Charrier, C., Salisbury, A-M., Moyo, E., Ooi, N., Chalam-Judge, N., Cheung, J., Stokes, N. R., Best, S., Craighead, M., Armer, R., Huxley, A..  (2020)  Rational design, synthesis and testing of novel tricyclic topoisomerase inhibitors for the treatment of bacterial infections part 2,  11  (12): [PMID:34095845] [10.1039/d0md00175a]

Source

Source(1):

• Scientific Literature