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

ID: ALA4088817

PubChem CID: 137644905

Max Phase: Preclinical

Molecular Formula: C23H26N6O2

Molecular Weight: 418.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)/C=C/c1cn([C@H]2C[C@@H](CO)N(Cc3ccccc3)C2)nn1

Standard InChI:  InChI=1S/C23H26N6O2/c24-21-8-4-5-9-22(21)25-23(31)11-10-18-14-29(27-26-18)19-12-20(16-30)28(15-19)13-17-6-2-1-3-7-17/h1-11,14,19-20,30H,12-13,15-16,24H2,(H,25,31)/b11-10+/t19-,20-/m0/s1

Standard InChI Key:  CTWOFTWQZAJGOE-FWEDTRJPSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   16.9736   -4.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9718   -5.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6814   -5.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3935   -5.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3892   -4.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6787   -3.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6811   -6.3558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1035   -5.5315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8116   -5.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5258   -5.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8138   -4.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2339   -5.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9440   -5.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0276   -6.3411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8306   -6.5100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2375   -5.7998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6881   -5.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0517   -5.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6011   -6.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3476   -5.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2615   -5.1693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4585   -5.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8706   -4.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0618   -6.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0597   -7.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6978   -3.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3097   -3.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1376   -2.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3545   -2.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7474   -2.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9201   -3.5708    0.0000 C   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
 20 24  1  6
 24 25  1  0
 23 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
M  END

Alternative Forms

1. Parent:

   

   ALA4088817

   ---

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: 418.50

Molecular Weight (Monoisotopic): 418.2117

AlogP: 2.32

#Rotatable Bonds: 7

Polar Surface Area: 109.30

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.33

CX LogP: 2.08

CX LogD: 1.10

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -1.01

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