(2S,4S)-4-(4-((E)-3-(2-aminophenylamino)-3-oxoprop-1-enyl)-1H-1,2,3-triazol-1-yl)-1-(3-phenylpropyl)pyrrolidine-2-carboxylic acid

ID: ALA4103036

PubChem CID: 137656876

Max Phase: Preclinical

Molecular Formula: C25H28N6O3

Molecular Weight: 460.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)/C=C/c1cn([C@H]2C[C@@H](C(=O)O)N(CCCc3ccccc3)C2)nn1

Standard InChI:  InChI=1S/C25H28N6O3/c26-21-10-4-5-11-22(21)27-24(32)13-12-19-16-31(29-28-19)20-15-23(25(33)34)30(17-20)14-6-9-18-7-2-1-3-8-18/h1-5,7-8,10-13,16,20,23H,6,9,14-15,17,26H2,(H,27,32)(H,33,34)/b13-12+/t20-,23-/m0/s1

Standard InChI Key:  PPETWBUGLLZQBC-MUHIBDNSSA-N

Molfile:  

     RDKit          2D

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    0.7726  -19.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822  -19.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983  -19.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941  -18.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836  -17.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6165  -19.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3266  -19.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146  -18.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0388  -19.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7489  -19.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284  -20.3958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0664  -19.2240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2634  -19.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6714  -18.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4534  -18.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0626  -18.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8446  -18.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0117  -19.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7883  -19.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3989  -19.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2249  -18.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4445  -18.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8625  -20.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8646  -21.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5706  -20.0349    0.0000 O   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
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 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
 23 24  1  0
 24 25  1  0
 25 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
 20 32  1  6
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103036

   ---

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: 460.54

Molecular Weight (Monoisotopic): 460.2223

AlogP: 2.85

#Rotatable Bonds: 9

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: 1.43

CX Basic pKa: 9.86

CX LogP: 0.41

CX LogD: 0.40

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.96

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