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

ID: ALA4086170

PubChem CID: 137642887

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-/m1/s1

Standard InChI Key:  CTWOFTWQZAJGOE-ANMDKAQQSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   18.8308   -3.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8291   -4.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5387   -4.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2507   -4.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2464   -3.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5360   -3.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5384   -5.5015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9608   -4.6772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6689   -4.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3831   -4.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6711   -3.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0912   -4.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8013   -4.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8849   -5.4868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6878   -5.6556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0948   -4.9455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5454   -4.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9089   -4.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4583   -5.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2048   -5.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1187   -4.3150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3158   -4.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7279   -3.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9190   -5.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9170   -6.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5550   -2.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1669   -2.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9948   -1.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2117   -1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6046   -1.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7773   -2.7164    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  1
 21 23  1  0
 20 24  1  1
 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:

   

   ALA4086170

   ---

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