(E)-3-(3-(4-(((3,4-difluorophenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-4-morpholinophenyl)but-2-enoic acid

ID: ALA4514705

PubChem CID: 155539508

Max Phase: Preclinical

Molecular Formula: C23H23F2N5O3

Molecular Weight: 455.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C(=C\C(=O)O)c1ccc(N2CCOCC2)c(-n2cc(CNc3ccc(F)c(F)c3)nn2)c1

Standard InChI:  InChI=1S/C23H23F2N5O3/c1-15(10-23(31)32)16-2-5-21(29-6-8-33-9-7-29)22(11-16)30-14-18(27-28-30)13-26-17-3-4-19(24)20(25)12-17/h2-5,10-12,14,26H,6-9,13H2,1H3,(H,31,32)/b15-10+

Standard InChI Key:  LZKOZFIYJDVJTN-XNTDXEJSSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.6636  -22.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624  -23.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3705  -23.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801  -23.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0773  -22.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687  -22.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558  -22.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9556  -21.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481  -22.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5403  -22.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8327  -22.6633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401  -21.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7885  -23.8891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7855  -24.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4898  -25.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1993  -24.7076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1999  -23.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4911  -23.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7831  -22.2452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5308  -22.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0754  -21.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641  -21.2592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654  -21.4322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8913  -21.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2996  -21.2573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168  -21.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5232  -21.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3396  -21.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7487  -21.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3355  -20.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5204  -20.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7413  -19.8376    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5659  -21.2555    0.0000 F   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
  1  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
  5 19  1  0
 21 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
 30 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514705

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 455.46

Molecular Weight (Monoisotopic): 455.1769

AlogP: 3.48

#Rotatable Bonds: 7

Polar Surface Area: 92.51

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.69

CX Basic pKa: 2.54

CX LogP: 3.37

CX LogD: 0.27

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: -1.63

References

1. Hu H, Li M, Wu D, Li Z, Miao R, Liu Y, Gong P..  (2019)  Design, synthesis and biological evaluation of novel aryl-acrylic derivatives as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors.,  27  (14): [PMID:31178268] [10.1016/j.bmc.2019.05.048]

Source

Source(1):

• Scientific Literature