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

ID: ALA4091229

PubChem CID: 137642605

Max Phase: Preclinical

Molecular Formula: C25H30N6O2

Molecular Weight: 446.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)/C=C/c1cn([C@@H]2C[C@@H](CO)N(CCCc3ccccc3)C2)nn1

Standard InChI:  InChI=1S/C25H30N6O2/c26-23-10-4-5-11-24(23)27-25(33)13-12-20-16-31(29-28-20)21-15-22(18-32)30(17-21)14-6-9-19-7-2-1-3-8-19/h1-5,7-8,10-13,16,21-22,32H,6,9,14-15,17-18,26H2,(H,27,33)/b13-12+/t21-,22+/m1/s1

Standard InChI Key:  KABCWLRJCDKRTD-UYEOAAJESA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   30.7710  -18.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7693  -19.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4789  -19.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1950  -19.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1908  -18.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4803  -18.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4786  -20.6128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9051  -19.7926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6132  -19.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3233  -19.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6113  -18.5610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0355  -19.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7456  -19.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8251  -20.6022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6280  -20.7710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0391  -20.0609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4897  -19.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8491  -19.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4027  -20.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1491  -20.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0631  -19.4304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2601  -19.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6681  -18.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4501  -19.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0593  -18.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8413  -18.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0084  -19.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7850  -19.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3956  -19.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2216  -18.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4412  -18.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8592  -20.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8613  -21.4729    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  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
 20 32  1  6
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091229

   ---

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: 446.56

Molecular Weight (Monoisotopic): 446.2430

AlogP: 2.75

#Rotatable Bonds: 9

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: 9.10

CX LogP: 2.82

CX LogD: 1.11

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -0.92

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