11-Cyanoimino-5-fluoro-9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-12-carboxylic acidmethyl ester

ID: ALA2252040

PubChem CID: 76308277

Max Phase: Preclinical

Molecular Formula: C14H13FN4O3

Molecular Weight: 304.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)N1/C(=N/C#N)NC2(C)CC1c1ccc(F)cc1O2

Standard InChI:  InChI=1S/C14H13FN4O3/c1-14-6-10(9-4-3-8(15)5-11(9)22-14)19(13(20)21-2)12(18-14)17-7-16/h3-5,10H,6H2,1-2H3,(H,17,18)

Standard InChI Key:  FSCYWQJABDASLW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   33.3672  -25.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3661  -26.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0741  -26.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0723  -25.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7810  -25.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7843  -26.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4967  -26.7394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2103  -26.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2069  -25.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4899  -25.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1917  -24.6726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9139  -25.9107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9060  -25.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6136  -24.6847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3215  -25.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0289  -25.5018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6126  -27.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6581  -26.7379    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.1904  -23.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8975  -23.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4821  -23.4478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6059  -23.8533    0.0000 C   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  1  0
  9 10  1  0
 10 11  1  0
  8 12  1  0
 11 13  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  3  0
  8 17  1  0
  2 18  1  0
 11 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252040

   Methyl 11-(cyanoamino)-5-fluoro-9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraene-12-carboxylate

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: 304.28

Molecular Weight (Monoisotopic): 304.0972

AlogP: 1.87

#Rotatable Bonds: ┄

Polar Surface Area: 86.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: -0.28

References

1. Finkelstein BL, Benner EA, Hendrixson MC, Kranis KT, Rauh JJ, Sethuraman MR, McCann SF..  (2002)  Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors.,  10  (3): [PMID:11814848] [10.1016/s0968-0896(01)00326-1]

Source

Source(1):

• Scientific Literature