5-Amino-7-((1aS,3aS,6aR,6bS)-6b-amino-octahydro-5-aza-cyclopropa[e]inden-5-yl)-6-fluoro-1-((1R,2S)-2-fluoro-cyclopropyl)-8-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

ID: ALA363725

PubChem CID: 10478620

Max Phase: Preclinical

Molecular Formula: C23H26F2N4O3

Molecular Weight: 444.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(N2C[C@H]3CC[C@H]4C[C@@]4(N)[C@H]3C2)c(F)c(N)c2c(=O)c(C(=O)O)cn([C@@H]3C[C@@H]3F)c12

Standard InChI:  InChI=1S/C23H26F2N4O3/c1-9-19-16(21(30)12(22(31)32)7-29(19)15-4-14(15)24)18(26)17(25)20(9)28-6-10-2-3-11-5-23(11,27)13(10)8-28/h7,10-11,13-15H,2-6,8,26-27H2,1H3,(H,31,32)/t10-,11+,13+,14+,15-,23+/m1/s1

Standard InChI Key:  MQSJWSMNALARNP-YXKLKYLKSA-N

Molfile:  

     RDKit          2D

 35 40  0  0  1  0  0  0  0  0999 V2000
    1.7167   -0.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167    1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458   -0.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0458   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167    2.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    0.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458    1.3875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    2.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    2.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -1.0917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6708    0.2625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208   -1.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -1.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3 14  1  0
  4  9  2  0
  5  1  1  0
  6  4  1  0
  7  1  1  1
  8 10  1  0
  9  1  1  0
 10 13  1  0
 11  2  2  0
 12 10  2  0
 13  5  2  0
 14 19  1  0
 15  7  1  0
 16  3  1  0
 17  3  1  0
 18  7  1  0
 19  8  1  0
 20  4  1  0
 21 22  1  0
 22  8  1  0
 23  6  2  0
  3 24  1  6
 25 28  1  0
 26 12  1  0
 27 20  2  0
 28 21  1  0
 29 11  1  0
 18 30  1  1
 31 20  1  0
 32 13  1  0
 14 33  1  6
 17 34  1  6
 21 35  1  6
 18 15  1  0
  2  6  1  0
 11 12  1  0
 14 21  1  0
 17 25  1  0
 17 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA363725

   7-[(3aS,5aS,6aS,6bR)-6a-amino-1,3,3a,4,5,5a,6,6b-octahydrocyclopropa[e]isoindol-2-yl]-5-amino-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-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: 444.48

Molecular Weight (Monoisotopic): 444.1973

AlogP: 2.58

#Rotatable Bonds: 3

Polar Surface Area: 114.58

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 9.76

CX LogP: -0.17

CX LogD: -0.17

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.63

Np Likeness Score: 0.52

References

1. Inagaki H, Takahashi H, Takemura M..  (2004)  Synthesis and antibacterial activity of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids bearing cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position.,  14  (20): [PMID:15380226] [10.1016/j.bmcl.2004.07.064]

Source

Source(1):

• Scientific Literature