2-(2-{4-[(2E)-3-(4-bromophenyl)prop-2-enamido]-2-fluorophenyl}-1,3-benzoxazol-5-yl)acetic acid

ID: ALA5285151

Max Phase: Preclinical

Molecular Formula: C24H16BrFN2O4

Molecular Weight: 495.30

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccc2oc(-c3ccc(NC(=O)/C=C/c4ccc(Br)cc4)cc3F)nc2c1

Standard InChI:  InChI=1S/C24H16BrFN2O4/c25-16-5-1-14(2-6-16)4-10-22(29)27-17-7-8-18(19(26)13-17)24-28-20-11-15(12-23(30)31)3-9-21(20)32-24/h1-11,13H,12H2,(H,27,29)(H,30,31)/b10-4+

Standard InChI Key:  BZHQBFMNCJCQPW-ONNFQVAWSA-N

Molfile:  

 
     RDKit          2D

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    2.9728   -0.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7691   -0.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -0.3008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7180   -0.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5430   -0.3026    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.3062    0.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811    0.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    1.1281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4660    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8786    1.1272    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1884    0.3651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 11 28  2  0
 28 29  1  0
 31  8  2  0
 31 32  1  0
  5 32  2  0
 10 30  2  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285151

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 495.30

Molecular Weight (Monoisotopic): 494.0277

AlogP: 5.68

#Rotatable Bonds: 6

Polar Surface Area: 92.43

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.53

CX Basic pKa: ┄

CX LogP: 5.49

CX LogD: 2.70

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -1.21

References

1. Jia L, Ma S..  (2016)  Recent advances in the discovery of heparanase inhibitors as anti-cancer agents.,  121  [PMID:27240275] [10.1016/j.ejmech.2016.05.052]

Source

Source(1):

• Scientific Literature