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

ID: ALA4061632

PubChem CID: 137636394

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-WYCPQIHASA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   16.6724  -18.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6707  -19.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3803  -19.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0964  -19.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0921  -18.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3817  -18.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3800  -20.7366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8065  -19.9164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5146  -19.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2247  -19.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5127  -18.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9369  -19.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6470  -19.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7265  -20.7260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5294  -20.8949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9405  -20.1847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3911  -19.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7505  -20.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3040  -20.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0505  -20.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9644  -19.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1615  -19.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5695  -19.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3515  -19.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9607  -18.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7427  -18.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9098  -19.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6864  -20.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2970  -19.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1230  -18.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3426  -18.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7606  -20.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7627  -21.5968    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  6
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4061632

   ---

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