(2R,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: ALA4084121

PubChem CID: 137645622

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-FNZLVXQQSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   28.8642  -18.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8625  -19.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5721  -19.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2883  -19.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2840  -18.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5735  -17.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5718  -20.2908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9983  -19.4707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7064  -19.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4165  -19.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7045  -18.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1287  -19.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8388  -19.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9183  -20.2803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7212  -20.4491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1323  -19.7390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5829  -19.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9424  -19.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4959  -20.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2423  -19.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1563  -19.1085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3533  -18.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7613  -18.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5433  -18.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1525  -18.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9345  -18.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1016  -19.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8782  -19.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4888  -19.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3148  -18.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5344  -17.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9525  -20.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9545  -21.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6605  -19.9193    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
 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
 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  1
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084121

   ---

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