(2R,4R)-4-(4-((E)-3-(2-aminophenylamino)-3-oxoprop-1-enyl)-1H-1,2,3-triazol-1-yl)-1-benzylpyrrolidine-2-carboxylic acid

ID: ALA4062411

PubChem CID: 137635275

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-/m1/s1

Standard InChI Key:  NDBHJVWINJBXCC-WFPNJVTPSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
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    2.8773   -4.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5869   -5.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5842   -3.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866   -6.0958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0090   -5.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7172   -4.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4313   -5.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7193   -4.0440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9331   -6.0811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7361   -6.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1430   -5.5398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2531   -5.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1670   -4.9093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3641   -4.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7762   -4.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9673   -6.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9652   -6.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6754   -5.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6033   -3.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2152   -3.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0431   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2600   -1.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6529   -2.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8256   -3.3108    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
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  6  1  1  0
  3  7  1  0
  4  8  1  0
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  9 10  1  0
  9 11  2  0
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 13 14  1  0
 14 15  2  0
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 17 13  2  0
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 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
 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:

   

   ALA4062411

   ---

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