(E)-N-(2-aminophenyl)-3-(1-((3S,5S)-5-(hydroxymethyl)-1-phenethylpyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)acrylamide

ID: ALA4060596

PubChem CID: 137637013

Max Phase: Preclinical

Molecular Formula: C24H28N6O2

Molecular Weight: 432.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)/C=C/c1cn([C@H]2C[C@@H](CO)N(CCc3ccccc3)C2)nn1

Standard InChI:  InChI=1S/C24H28N6O2/c25-22-8-4-5-9-23(22)26-24(32)11-10-19-15-30(28-27-19)20-14-21(17-31)29(16-20)13-12-18-6-2-1-3-7-18/h1-11,15,20-21,31H,12-14,16-17,25H2,(H,26,32)/b11-10+/t20-,21-/m0/s1

Standard InChI Key:  FKXOJPSNJLPRGP-YGEFIYNQSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   16.4586  -11.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4569  -12.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1665  -12.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8786  -12.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8743  -11.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1638  -11.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1662  -13.6743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5886  -12.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2967  -12.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0068  -12.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2948  -11.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7190  -12.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4291  -12.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5127  -13.6596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3157  -13.8284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7226  -13.1183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1732  -12.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5368  -13.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0862  -13.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8326  -13.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7466  -12.4878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9436  -12.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3557  -11.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1336  -12.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7428  -11.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5200  -11.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1287  -11.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9562  -10.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1710  -10.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5674  -10.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428  -13.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5448  -14.5344    0.0000 O   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  1  1  0
  3  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18 16  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 20 31  1  6
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4060596

   ---

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: 432.53

Molecular Weight (Monoisotopic): 432.2274

AlogP: 2.36

#Rotatable Bonds: 8

Polar Surface Area: 109.30

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.69

CX LogP: 2.37

CX LogD: 1.06

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: -0.91

References

1. Tian Y, Lv W, Li X, Wang C, Wang D, Wang PG, Jin J, Shen J..  (2017)  Stabilizing HDAC11 with SAHA to assay slow-binding benzamide inhibitors.,  27  (13): [PMID:28501514] [10.1016/j.bmcl.2017.05.004]

Source

Source(1):

• Scientific Literature