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

ID: ALA4085088

PubChem CID: 137647803

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-ZXFANKLMSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   14.0019   -3.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0002   -3.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7098   -4.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4219   -3.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4176   -3.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7071   -2.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7095   -5.2249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1319   -4.4007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8400   -3.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5542   -4.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8422   -3.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2623   -3.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9724   -4.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0560   -5.2102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8590   -5.3791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2659   -4.6690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7165   -4.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0801   -4.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6295   -5.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3759   -4.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2899   -4.0384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4869   -3.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8990   -3.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0902   -5.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0881   -6.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7983   -4.8534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7262   -2.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3380   -2.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1660   -1.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3829   -1.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7758   -1.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9485   -2.4399    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  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:

   

   ALA4085088

   ---

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