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

ID: ALA2252183

PubChem CID: 76311925

Max Phase: Preclinical

Molecular Formula: C14H14N4O3

Molecular Weight: 286.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)N1/C(=N/C#N)NC2(C)CC1c1ccccc1O2

Standard InChI:  InChI=1S/C14H14N4O3/c1-14-7-10(9-5-3-4-6-11(9)21-14)18(13(19)20-2)12(17-14)16-8-15/h3-6,10H,7H2,1-2H3,(H,16,17)

Standard InChI Key:  BJCOLLHCLGVZQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   25.9052   -6.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9041   -6.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6121   -7.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6103   -5.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3189   -6.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3223   -6.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0347   -7.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7483   -6.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7449   -6.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0279   -5.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7296   -5.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4519   -6.4674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4440   -5.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1516   -5.2414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8594   -5.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5669   -6.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1506   -7.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7284   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4355   -4.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0201   -4.0045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1438   -4.4099    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
 18 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252183

   Methyl 11-(cyanoamino)-9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6,10-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: 286.29

Molecular Weight (Monoisotopic): 286.1066

AlogP: 1.74

#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: 2.15

CX LogD: 2.15

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: -0.13

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