(Z)-(8-bromo-(E)-2-styrylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylideno)acetaldehyde

ID: ALA436520

PubChem CID: 44419654

Max Phase: Preclinical

Molecular Formula: C20H12BrNO3

Molecular Weight: 394.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C/C=C1\OC(/C=C/c2ccccc2)=Nc2c1oc1ccc(Br)cc21

Standard InChI:  InChI=1S/C20H12BrNO3/c21-14-7-8-16-15(12-14)19-20(25-16)17(10-11-23)24-18(22-19)9-6-13-4-2-1-3-5-13/h1-12H/b9-6+,17-10-

Standard InChI Key:  SGBVSZSOAXVGLQ-XEWCJNAKSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -3.0405  -11.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013  -12.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800  -12.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614  -10.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410  -10.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990  -11.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5730  -11.3516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263  -10.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031  -10.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168  -10.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3147   -9.2901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132   -8.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1302   -9.2963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323  -10.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -8.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2931   -7.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877   -6.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059   -6.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0009   -5.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832   -5.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309   -5.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224   -6.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8614  -11.1936    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7457  -10.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437   -9.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
 13  8  1  0
  3  6  2  0
 10 14  2  0
  6  7  1  0
 12 15  1  0
  7  9  1  0
 15 16  2  0
  8  5  1  0
 16 17  1  0
  1  2  2  0
 17 18  2  0
  5  4  2  0
 18 19  1  0
  8  9  2  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
  1 23  1  0
 10 11  1  0
 14 24  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA436520

   (2Z)-2-[8-bromo-2-[(E)-2-phenylethenyl]-[1]benzofuro[3,2-d][1,3]oxazin-4-ylidene]acetaldehyde

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: 394.22

Molecular Weight (Monoisotopic): 393.0001

AlogP: 5.51

#Rotatable Bonds: 3

Polar Surface Area: 51.80

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.64

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: 0.09

References

1. Ando Y, Ando K, Yamaguchi M, Kunitomo J, Koida M, Fukuyama R, Nakamuta H, Yamashita M, Ohta S, Ohishi Y..  (2006)  A novel oxazine ring closure reaction affording (Z)-((E)-2-styrylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylideno)acetaldehydes and their anti-osteoclastic bone resorption activity.,  16  (22): [PMID:16945531] [10.1016/j.bmcl.2006.08.064]

2. Tabuchi Y, Ando Y, Kanemura H, Kawasaki I, Ohishi T, Koida M, Fukuyama R, Nakamuta H, Ohta S, Nishide K, Ohishi Y..  (2009)  Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity.,  17  (11): [PMID:19406645] [10.1016/j.bmc.2009.04.017]

Source

Source(1):

• Scientific Literature