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

ID: ALA2252032

PubChem CID: 76311917

Max Phase: Preclinical

Molecular Formula: C16H18N4O2

Molecular Weight: 298.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H18N4O2/c1-10(2)14(21)20-12-8-16(3,19-15(20)18-9-17)22-13-7-5-4-6-11(12)13/h4-7,10,12H,8H2,1-3H3,(H,18,19)

Standard InChI Key:  WIQYKJKCQRTHRR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   18.8930  -22.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8919  -23.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5999  -23.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5981  -22.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3068  -22.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3102  -23.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0225  -23.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7361  -23.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7327  -22.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0158  -22.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7175  -21.8784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4397  -23.1166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4319  -22.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1394  -21.8906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8473  -22.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5547  -22.7077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1385  -24.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7163  -21.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4233  -20.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1317  -21.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0079  -20.6537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4221  -19.8344    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  1  0
 18 21  2  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252032

   [9-Methyl-12-(2-methylpropanoyl)-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: 298.35

Molecular Weight (Monoisotopic): 298.1430

AlogP: 2.15

#Rotatable Bonds: 1

Polar Surface Area: 77.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.33

CX LogP: 2.77

CX LogD: 2.77

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -0.25

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