rel-endo-(1R,9R,13S)-9,13-dimethyl-8-oxa-10,12-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-trien-11-ylidene-cyanamide

ID: ALA2252042

PubChem CID: 76319145

Max Phase: Preclinical

Molecular Formula: C13H14N4O

Molecular Weight: 242.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@H]2N/C(=N/C#N)N[C@]1(C)Oc1ccccc12

Standard InChI:  InChI=1S/C13H14N4O/c1-8-11-9-5-3-4-6-10(9)18-13(8,2)17-12(16-11)15-7-14/h3-6,8,11H,1-2H3,(H2,15,16,17)/t8-,11+,13+/m0/s1

Standard InChI Key:  YVPPUWUWVRMDGI-RLCGTCKNSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   11.9526   -8.1047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6451   -7.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3378   -7.3081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9038   -7.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2221   -7.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5189   -7.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8201   -7.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8201   -6.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5201   -6.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2048   -6.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8982   -6.1467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5908   -6.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2681   -6.9403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2681   -7.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5866   -8.1047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6031   -7.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8295   -7.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9914   -5.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  3  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  4 15  1  1
  4 16  1  0
 12 16  1  0
  5 10  1  0
 16 17  1  1
 12 18  1  6
  1 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252042

   [(1R,9R,13S)-9,13-dimethyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6,11-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: 242.28

Molecular Weight (Monoisotopic): 242.1168

AlogP: 1.50

#Rotatable Bonds: ┄

Polar Surface Area: 69.44

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: 2.02

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.68

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