12-Benzyl-9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.02,7]-trideca-2,4,6-trien-11-ylidene-cyanamide

ID: ALA2252016

PubChem CID: 76329976

Max Phase: Preclinical

Molecular Formula: C19H18N4O

Molecular Weight: 318.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CC(c3ccccc3O1)N(Cc1ccccc1)/C(=N/C#N)N2

Standard InChI:  InChI=1S/C19H18N4O/c1-19-11-16(15-9-5-6-10-17(15)24-19)23(18(22-19)21-13-20)12-14-7-3-2-4-8-14/h2-10,16H,11-12H2,1H3,(H,21,22)

Standard InChI Key:  NWJWJKYJRZDDIN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   33.6974  -10.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6963  -11.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4043  -11.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4025   -9.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1111  -10.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1145  -11.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8269  -11.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5405  -11.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5371  -10.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8201   -9.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5218   -9.3936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2441  -10.6317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2362   -9.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9438   -9.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6516   -9.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3591  -10.2228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9428  -11.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5206   -8.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2277   -8.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9329   -8.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6395   -8.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6387   -7.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9254   -6.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2217   -7.3527    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
 11 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252016

   (12-Benzyl-9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6,10-tetraen-11-yl)cyanamide

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: 318.38

Molecular Weight (Monoisotopic): 318.1481

AlogP: 3.17

#Rotatable Bonds: 2

Polar Surface Area: 60.65

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: -0.36

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