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

ID: ALA4070300

PubChem CID: 137639071

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-HZYCFNBMSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   30.0579  -10.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0561  -11.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7657  -12.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4778  -11.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4735  -10.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7630  -10.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7654  -12.8694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1878  -12.0452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8960  -11.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6060  -12.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8940  -10.8136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3183  -11.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0283  -12.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1119  -12.8547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9149  -13.0236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3218  -12.3135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7724  -11.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1360  -12.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6854  -12.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4319  -12.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3458  -11.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5429  -11.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9550  -11.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7328  -11.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3420  -10.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1193  -11.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7279  -10.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5554   -9.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7702   -9.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1666  -10.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1420  -12.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1440  -13.7296    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  6
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4070300

   ---

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