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

ID: ALA4083442

PubChem CID: 137647722

Max Phase: Preclinical

Molecular Formula: C23H26N6O2

Molecular Weight: 418.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)/C=C/c1cn([C@@H]2C[C@@H](CO)N(Cc3ccccc3)C2)nn1

Standard InChI:  InChI=1S/C23H26N6O2/c24-21-8-4-5-9-22(21)25-23(31)11-10-18-14-29(27-26-18)19-12-20(16-30)28(15-19)13-17-6-2-1-3-7-17/h1-11,14,19-20,30H,12-13,15-16,24H2,(H,25,31)/b11-10+/t19-,20+/m1/s1

Standard InChI Key:  CTWOFTWQZAJGOE-WNGAPAKLSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   29.8381   -3.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8364   -4.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5460   -4.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2580   -4.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2537   -3.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5433   -3.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5457   -5.5551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9681   -4.7308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6762   -4.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3904   -4.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6784   -3.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0985   -4.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8086   -4.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8922   -5.5404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6951   -5.7093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1021   -4.9991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5527   -4.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9163   -4.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4657   -5.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2121   -5.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1261   -4.3686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3231   -4.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7352   -3.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9264   -5.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9243   -6.4153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5624   -3.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1742   -2.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0021   -1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2191   -1.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6119   -1.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7847   -2.7701    0.0000 C   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  1
 21 23  1  0
 20 24  1  6
 24 25  1  0
 23 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:

   

   ALA4083442

   ---

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: 418.50

Molecular Weight (Monoisotopic): 418.2117

AlogP: 2.32

#Rotatable Bonds: 7

Polar Surface Area: 109.30

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.33

CX LogP: 2.08

CX LogD: 1.10

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -1.01

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