3-(1-(3-Dimethylamino-2-hydroxy-propyl)-1H-indol-3-yl)-2-cyano-N-octylacrylamide

ID: ALA2312414

PubChem CID: 71546501

Max Phase: Preclinical

Molecular Formula: C25H36N4O2

Molecular Weight: 424.59

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H36N4O2/c1-4-5-6-7-8-11-14-27-25(31)20(16-26)15-21-17-29(19-22(30)18-28(2)3)24-13-10-9-12-23(21)24/h9-10,12-13,15,17,22,30H,4-8,11,14,18-19H2,1-3H3,(H,27,31)/b20-15+

Standard InChI Key:  HRFWBDGUUMUKRE-HMMYKYKNSA-N

Molfile:  

     RDKit          2D

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    2.0152  -14.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0140  -15.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7289  -15.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271  -14.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424  -14.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4426  -15.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2327  -15.5850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214  -14.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2323  -14.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426  -13.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676  -13.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7029  -12.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4633  -12.0928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1176  -13.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9426  -13.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3572  -14.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5968  -14.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8364  -15.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6614  -15.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8840  -14.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2986  -14.9514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2205  -16.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000  -16.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4878  -17.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673  -18.0386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550  -18.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591  -17.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917  -16.3888    0.0000 O   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  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2312414

   (E)-2-cyano-3-[1-[3-(dimethylamino)-2-hydroxypropyl]indol-3-yl]-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: 424.59

Molecular Weight (Monoisotopic): 424.2838

AlogP: 3.95

#Rotatable Bonds: 13

Polar Surface Area: 81.29

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.09

CX LogP: 4.18

CX LogD: 2.48

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -1.13

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