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

ID: ALA4104078

PubChem CID: 137657344

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+/m0/s1

Standard InChI Key:  KABCWLRJCDKRTD-JSJGNVMISA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.4859  -17.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4842  -18.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1938  -18.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099  -18.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9056  -17.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1952  -17.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935  -19.6140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6200  -18.7938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3281  -18.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0382  -18.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3262  -17.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7504  -18.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4605  -18.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400  -19.6034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3429  -19.7723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7540  -19.0621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2046  -18.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7779  -18.4316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9750  -18.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3830  -17.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1650  -18.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7742  -17.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5562  -17.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7233  -18.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4999  -18.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1105  -18.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9365  -17.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1561  -17.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5741  -19.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5762  -20.4741    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  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  1
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104078

   ---

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