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

ID: ALA4092137

PubChem CID: 137653922

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-RRCSEMEMSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.5601   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5583   -3.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679   -4.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9800   -3.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9757   -3.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2652   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2676   -5.1507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900   -4.3264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3981   -3.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1123   -4.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4003   -3.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8205   -3.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5305   -4.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6141   -5.1360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4171   -5.3048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8240   -4.5947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2746   -3.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6382   -4.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1876   -5.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9341   -4.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8480   -3.9641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0451   -3.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4571   -3.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6483   -5.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6462   -6.0108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2843   -2.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8962   -2.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7241   -1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9410   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3339   -1.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5066   -2.3656    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  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:

   

   ALA4092137

   ---

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