allyl 4-(4-(pyrazine-2-carboxamido)phenoxy)phenylcarbamate

ID: ALA2269042

PubChem CID: 10691792

Max Phase: Preclinical

Molecular Formula: C21H18N4O4

Molecular Weight: 390.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCOC(=O)Nc1ccc(Oc2ccc(NC(=O)c3cnccn3)cc2)cc1

Standard InChI:  InChI=1S/C21H18N4O4/c1-2-13-28-21(27)25-16-5-9-18(10-6-16)29-17-7-3-15(4-8-17)24-20(26)19-14-22-11-12-23-19/h2-12,14H,1,13H2,(H,24,26)(H,25,27)

Standard InChI Key:  SCEFWXKSMVSSLU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   32.8073  -19.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5129  -19.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2227  -19.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0975  -19.5514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4294  -17.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4282  -17.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1363  -18.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8459  -17.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8431  -17.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1345  -16.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7202  -18.3514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5493  -16.7090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2585  -17.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2582  -17.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9667  -18.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6738  -17.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6681  -17.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9591  -16.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0128  -17.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3048  -18.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0134  -17.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5981  -17.9389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8906  -18.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8895  -19.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6019  -19.5734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3065  -19.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3836  -18.3293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3877  -19.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6821  -19.5587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  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
  6 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 11 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 16 27  1  0
 27 28  1  0
 28  4  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269042

   prop-2-enyl N-[4-[4-(pyrazine-2-carbonylamino)phenoxy]phenyl]carbamate

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: 390.40

Molecular Weight (Monoisotopic): 390.1328

AlogP: 4.26

#Rotatable Bonds: 7

Polar Surface Area: 102.44

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.16

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -1.22

References

1. Balcells M, Avilla J, Profitos J, Canela R..  (2000)  Synthesis of phenoxyphenyl pyridine and pyrazine carboxamides. Activity against Cydia pomonella (L.) eggs.,  48  (1): [PMID:10637056] [10.1021/jf990404e]

Source

Source(1):

• Scientific Literature