(11-Cyanoimino-9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-trien-12-yl)-acetic acid methylester

ID: ALA2252028

PubChem CID: 76319143

Max Phase: Preclinical

Molecular Formula: C15H16N4O3

Molecular Weight: 300.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CN1/C(=N/C#N)NC2(C)CC1c1ccccc1O2

Standard InChI:  InChI=1S/C15H16N4O3/c1-15-7-11(10-5-3-4-6-12(10)22-15)19(8-13(20)21-2)14(18-15)17-9-16/h3-6,11H,7-8H2,1-2H3,(H,17,18)

Standard InChI Key:  PIPPNTBVVWVZAK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   33.1113  -18.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1102  -19.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8182  -19.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8164  -18.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5251  -18.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5285  -19.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2408  -19.8304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9544  -19.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9510  -18.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2341  -18.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9358  -17.7636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6580  -19.0018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6502  -18.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3577  -17.7758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0656  -18.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7730  -18.5928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3568  -20.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9346  -16.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6416  -16.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6404  -15.7196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3500  -16.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0571  -16.5346    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
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252028

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

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: 300.32

Molecular Weight (Monoisotopic): 300.1222

AlogP: 1.14

#Rotatable Bonds: 2

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: 1.54

CX LogD: 1.54

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: -0.34

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