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

ID: ALA2252021

PubChem CID: 76326365

Max Phase: Preclinical

Molecular Formula: C18H17N5O

Molecular Weight: 319.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CC(c3ccccc3O1)N(Cc1ccccn1)/C(=N/C#N)N2

Standard InChI:  InChI=1S/C18H17N5O/c1-18-10-15(14-7-2-3-8-16(14)24-18)23(17(22-18)21-12-19)11-13-6-4-5-9-20-13/h2-9,15H,10-11H2,1H3,(H,21,22)

Standard InChI Key:  ZYVSDJIJCDESAH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   26.3798  -14.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3787  -15.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0867  -16.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0849  -14.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7936  -14.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7969  -15.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5093  -16.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2229  -15.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2195  -14.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5025  -14.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2043  -14.1192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9265  -15.3574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9186  -14.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6262  -14.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3341  -14.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0415  -14.9485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6252  -16.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2030  -13.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9101  -12.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6153  -13.3014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3219  -12.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3211  -12.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6078  -11.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9041  -12.0783    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:

   

   ALA2252021

   [9-Methyl-12-(pyridin-2-ylmethyl)-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: 319.37

Molecular Weight (Monoisotopic): 319.1433

AlogP: 2.56

#Rotatable Bonds: 2

Polar Surface Area: 73.54

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.58

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: -0.79

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