3-(1-Benzyl-1H-indol-3-yl)-2-cyano-N-octylacrylamide

ID: ALA2312423

PubChem CID: 71546657

Max Phase: Preclinical

Molecular Formula: C27H31N3O

Molecular Weight: 413.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCNC(=O)/C(C#N)=C/c1cn(Cc2ccccc2)c2ccccc12

Standard InChI:  InChI=1S/C27H31N3O/c1-2-3-4-5-6-12-17-29-27(31)23(19-28)18-24-21-30(20-22-13-8-7-9-14-22)26-16-11-10-15-25(24)26/h7-11,13-16,18,21H,2-6,12,17,20H2,1H3,(H,29,31)/b23-18+

Standard InChI Key:  RGYHMUNUESFCCV-PTGBLXJZSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   12.9734   -9.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9722  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6870  -10.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6852   -8.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4006   -9.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4009  -10.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1911  -10.3180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6796   -9.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1905   -8.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6008   -8.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4257   -8.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8361   -7.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6611   -7.5369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4215   -6.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0757   -8.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9007   -8.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3153   -8.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1403   -8.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5549   -9.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3799   -9.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7946  -10.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6196  -10.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8422   -8.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2568   -9.6848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1880  -11.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4722  -11.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7635  -11.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0481  -11.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0448  -12.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7629  -12.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4753  -12.3742    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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  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
 23 24  3  0
 11 23  1  0
  7 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2312423

   (E)-3-(1-benzylindol-3-yl)-2-cyano-N-octylprop-2-enamide

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: 413.57

Molecular Weight (Monoisotopic): 413.2467

AlogP: 6.07

#Rotatable Bonds: 11

Polar Surface Area: 57.82

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.51

CX LogD: 6.51

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.24

Np Likeness Score: -1.07

References

1. Gordon CP, Venn-Brown B, Robertson MJ, Young KA, Chau N, Mariana A, Whiting A, Chircop M, Robinson PJ, McCluskey A..  (2013)  Development of second-generation indole-based dynamin GTPase inhibitors.,  56  (1): [PMID:23167654] [10.1021/jm300844m]

Source

Source(1):

• Scientific Literature