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

ID: ALA4096328

PubChem CID: 137655942

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-/m1/s1

Standard InChI Key:  FKXOJPSNJLPRGP-VRDGUJSXSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   17.9940  -10.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9922  -11.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7018  -11.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4139  -11.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4096  -10.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6991  -10.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7015  -12.6961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1240  -11.8718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8321  -11.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5421  -11.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8301  -10.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2544  -11.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9644  -11.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0481  -12.6814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8510  -12.8503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2579  -12.1401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7085  -11.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0721  -12.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6215  -12.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3680  -12.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2819  -11.5096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4790  -11.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8911  -10.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6690  -11.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2781  -10.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0554  -10.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6640  -10.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4916   -9.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7064   -9.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1028   -9.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0781  -12.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0801  -13.5563    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  1
 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  1
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096328

   ---

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