5,6-Dimethoxy-9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6,11-tetraen-11-yl-cyanamide

ID: ALA2252022

PubChem CID: 76329978

Max Phase: Preclinical

Molecular Formula: C14H16N4O3

Molecular Weight: 288.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1OC)OC1(C)CC2N/C(=N/C#N)N1

Standard InChI:  InChI=1S/C14H16N4O3/c1-14-6-9(17-13(18-14)16-7-15)8-4-5-10(19-2)12(20-3)11(8)21-14/h4-5,9H,6H2,1-3H3,(H2,16,17,18)

Standard InChI Key:  MRXPYJVYRYEXIU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   34.4733  -13.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4722  -14.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1802  -14.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1784  -13.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8871  -13.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8904  -14.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6028  -14.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3164  -14.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3130  -13.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5960  -13.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2978  -12.7696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0200  -14.0078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0121  -13.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7197  -12.7818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4276  -13.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1350  -13.5989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7187  -15.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7641  -14.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0568  -14.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1788  -15.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4704  -16.0605    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
 18 19  1  0
  3 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252022

   (5,6-Dimethoxy-9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2(7),3,5,11-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: 288.31

Molecular Weight (Monoisotopic): 288.1222

AlogP: 1.27

#Rotatable Bonds: 2

Polar Surface Area: 87.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.33

CX LogD: 1.33

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: 0.45

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