(2S,4S)-4-(4-((E)-3-((2-aminophenyl)amino)-3-oxoprop-1-en-1-yl)-1H-1,2,3-triazol-1-yl)-1-benzylpyrrolidine-2-carboxylic acid

ID: ALA4095285

PubChem CID: 137653114

Max Phase: Preclinical

Molecular Formula: C23H24N6O3

Molecular Weight: 432.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H24N6O3/c24-19-8-4-5-9-20(19)25-22(30)11-10-17-14-29(27-26-17)18-12-21(23(31)32)28(15-18)13-16-6-2-1-3-7-16/h1-11,14,18,21H,12-13,15,24H2,(H,25,30)(H,31,32)/b11-10+/t18-,21-/m0/s1

Standard InChI Key:  NDBHJVWINJBXCC-KKMKJULVSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    1.1374   -3.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356   -4.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452   -5.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5573   -4.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5530   -3.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425   -3.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449   -6.0256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2674   -5.2013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9755   -4.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6897   -5.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777   -3.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3978   -4.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1078   -5.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914   -6.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9944   -6.1798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4013   -5.4696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8519   -4.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2155   -5.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7649   -5.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5114   -5.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4253   -4.8391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6224   -4.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0345   -4.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2256   -6.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2235   -6.8858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9337   -5.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8616   -3.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4735   -2.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3014   -2.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5183   -1.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9112   -2.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0839   -3.2406    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
 24 26  2  0
 23 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095285

   ---

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: 432.48

Molecular Weight (Monoisotopic): 432.1910

AlogP: 2.41

#Rotatable Bonds: 7

Polar Surface Area: 126.37

Molecular Species: ZWITTERION

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.30

CX Basic pKa: 9.09

CX LogP: -0.33

CX LogD: -0.33

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.10

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