1-[(4-Nitrophenyl)carbamoyl]cyclohexyl cinnamate

ID: ALA4476481

PubChem CID: 155538412

Max Phase: Preclinical

Molecular Formula: C22H22N2O5

Molecular Weight: 394.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1)OC1(C(=O)Nc2ccc([N+](=O)[O-])cc2)CCCCC1

Standard InChI:  InChI=1S/C22H22N2O5/c25-20(14-9-17-7-3-1-4-8-17)29-22(15-5-2-6-16-22)21(26)23-18-10-12-19(13-11-18)24(27)28/h1,3-4,7-14H,2,5-6,15-16H2,(H,23,26)/b14-9+

Standard InChI Key:  VBJDZCNBGHTHCU-NTEUORMPSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   30.5332  -14.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2390  -13.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2345  -13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5258  -12.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8200  -13.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8230  -13.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9989  -14.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9978  -15.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7058  -15.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4155  -15.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4126  -14.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7040  -14.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2878  -15.9366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2872  -16.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5805  -15.5275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1188  -14.2904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8281  -14.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8311  -15.5135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2435  -14.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9496  -14.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6589  -14.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9465  -13.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3599  -14.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0707  -14.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0736  -15.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7835  -15.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4891  -15.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4804  -14.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7699  -14.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 13 14  2  0
 13 15  1  0
  8 13  1  0
 11 16  1  0
 16 17  1  0
 17  1  1  0
 17 18  2  0
  1 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 23 21  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  CHG  2  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4476481

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.43

Molecular Weight (Monoisotopic): 394.1529

AlogP: 4.49

#Rotatable Bonds: 6

Polar Surface Area: 98.54

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.87

CX Basic pKa: ┄

CX LogP: 5.40

CX LogD: 5.39

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -0.25

References

1. Salah Ayoup M, Wahby Y, Abdel-Hamid H, Ramadan ES, Teleb M, Abu-Serie MM, Noby A..  (2019)  Design, synthesis and biological evaluation of novel α-acyloxy carboxamides via Passerini reaction as caspase 3/7 activators.,  168  [PMID:30826510] [10.1016/j.ejmech.2019.02.051]

Source

Source(1):

• Scientific Literature