(4-{[4-(4-fluoro-phenylamino)-6-piperidin-1-yl-[1,3,5]triazin-2-yl]-hydrazonomethyl}-2-methoxy-phenoxy)-acetic acid

ID: ALA209055

Max Phase: Preclinical

Molecular Formula: C24H26FN7O4

Molecular Weight: 495.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=N/Nc2nc(Nc3ccc(F)cc3)nc(N3CCCCC3)n2)ccc1OCC(=O)O

Standard InChI:  InChI=1S/C24H26FN7O4/c1-35-20-13-16(5-10-19(20)36-15-21(33)34)14-26-31-23-28-22(27-18-8-6-17(25)7-9-18)29-24(30-23)32-11-3-2-4-12-32/h5-10,13-14H,2-4,11-12,15H2,1H3,(H,33,34)(H2,27,28,29,30,31)/b26-14+

Standard InChI Key:  SFLXZAPPMTUXAE-VULFUBBASA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    1.9362   -6.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -6.4442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5150   -6.9298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -6.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622   -5.6734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8639   -5.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908   -5.6330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -6.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093   -6.8909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362   -6.8568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402   -4.4162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1140   -4.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5836   -4.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -4.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3335   -3.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6261   -2.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966   -3.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689   -6.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616   -6.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938   -6.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324   -5.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327   -5.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032   -5.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4679   -4.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8647   -5.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1993   -3.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5600   -5.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2923   -5.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9877   -5.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3293   -4.5037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -2.8514    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0396   -6.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619   -6.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866   -7.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0827   -8.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -7.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  1 18  1  0
  9  4  1  0
 18 19  2  0
  4  5  2  0
 19 20  1  0
  8 10  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  6 11  1  0
 22 23  2  0
 23 18  1  0
  5  6  1  0
 22 24  1  0
 11 12  1  0
 21 25  1  0
  1  2  2  0
 24 26  1  0
 12 13  2  0
 25 27  1  0
  6  7  2  0
 27 28  1  0
 13 14  1  0
 28 29  1  0
  3  4  1  0
 28 30  2  0
 14 15  2  0
 15 31  1  0
 10 32  1  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 36  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA209055

   ---

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: 495.52

Molecular Weight (Monoisotopic): 495.2030

AlogP: 3.66

#Rotatable Bonds: 10

Polar Surface Area: 134.09

Molecular Species: ACID

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.18

CX Basic pKa: 5.07

CX LogP: 3.60

CX LogD: 1.97

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: -1.58

References

1. Dayam R, Aiello F, Deng J, Wu Y, Garofalo A, Chen X, Neamati N..  (2006)  Discovery of small molecule integrin alphavbeta3 antagonists as novel anticancer agents.,  49  (15): [PMID:16854058] [10.1021/jm051296s]

2. Al-Nadaf A, Abu Sheikha G, Taha MO..  (2010)  Elaborate ligand-based pharmacophore exploration and QSAR analysis guide the synthesis of novel pyridinium-based potent beta-secretase inhibitory leads.,  18  (9): [PMID:20378363] [10.1016/j.bmc.2010.03.043]

Source

Source(1):

• Scientific Literature