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

ID: ALA4080937

PubChem CID: 137646189

Max Phase: Preclinical

Molecular Formula: C24H26N6O3

Molecular Weight: 446.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)/C=C/c1cn([C@@H]2C[C@H](C(=O)O)N(CCc3ccccc3)C2)nn1

Standard InChI:  InChI=1S/C24H26N6O3/c25-20-8-4-5-9-21(20)26-23(31)11-10-18-15-30(28-27-18)19-14-22(24(32)33)29(16-19)13-12-17-6-2-1-3-7-17/h1-11,15,19,22H,12-14,16,25H2,(H,26,31)(H,32,33)/b11-10+/t19-,22-/m1/s1

Standard InChI Key:  HIULRIYRAKJRNA-VTXMGJMISA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    2.3642  -11.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624  -12.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720  -12.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7841  -12.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798  -11.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693  -10.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717  -13.4142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4941  -12.5900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2023  -12.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9123  -12.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003  -11.3584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246  -12.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3346  -12.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4182  -13.3995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2212  -13.5684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6281  -12.8583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0787  -12.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4423  -12.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917  -13.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7382  -13.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6521  -12.2277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8492  -12.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2613  -11.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0391  -11.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6483  -11.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4256  -11.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0342  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8617  -10.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0765  -10.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4729  -10.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4483  -13.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4503  -14.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1605  -13.0427    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  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 20 31  1  1
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4080937

   ---

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: 446.51

Molecular Weight (Monoisotopic): 446.2066

AlogP: 2.45

#Rotatable Bonds: 8

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: 1.41

CX Basic pKa: 9.95

CX LogP: -0.04

CX LogD: -0.04

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: -0.95

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