US9162991, 4f

ID: ALA3970044

PubChem CID: 25053516

Max Phase: Preclinical

Molecular Formula: C18H20N4O3

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cn(CC2CCCCC2)nn1

Standard InChI:  InChI=1S/C18H20N4O3/c23-18(11-8-14-6-9-16(10-7-14)22(24)25)17-13-21(20-19-17)12-15-4-2-1-3-5-15/h6-11,13,15H,1-5,12H2/b11-8+

Standard InChI Key:  ROTCCCLUIDMNNB-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -6.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6332   -7.5468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5071   -8.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900  -10.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631  -11.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1435  -12.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507  -12.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774  -11.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971  -10.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332   -7.5416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -6.1134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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  5  1  0
  8 11  1  0
 11 12  1  0
 11 13  2  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  1  0
 16 24  1  0
 24 25  2  0
 25 14  1  0
M  CHG  2  11   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3970044

   (E)-1-[1-(cyclohexylmethyl)triazol-4-yl]-3-(4-nitrophenyl)prop-2-en-1-one

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: 340.38

Molecular Weight (Monoisotopic): 340.1535

AlogP: 3.66

#Rotatable Bonds: 6

Polar Surface Area: 90.92

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 4.38

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.35

Np Likeness Score: -1.32

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database