7-(2-Bromophenyl)-3-methyl-2-(4-nitrophenyl)-7,8-dihydro-2H-3,8a-epidioxypyrano[4,3-b]pyran-5(3H)-one

ID: ALA2435076

PubChem CID: 73349378

Max Phase: Preclinical

Molecular Formula: C21H16BrNO7

Molecular Weight: 474.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12C=C3C(=O)OC(c4ccccc4Br)C[C@@]3(OO1)OC2c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C21H16BrNO7/c1-20-10-15-19(24)27-17(14-4-2-3-5-16(14)22)11-21(15,30-29-20)28-18(20)12-6-8-13(9-7-12)23(25)26/h2-10,17-18H,11H2,1H3/t17?,18?,20-,21+/m1/s1

Standard InChI Key:  RHPHEJQZMPXNFE-FMFRFZGHSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    5.2993   -8.8697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135   -8.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135   -7.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2993   -7.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801   -7.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6443   -8.1325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7304   -8.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6225   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851   -8.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862   -7.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750   -7.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582   -7.6301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1571   -8.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8729   -8.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8772   -6.4253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4691   -8.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7815   -8.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927   -8.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -9.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827  -10.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -9.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280   -9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4441  -10.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1629   -9.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1612   -8.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4445   -8.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8534  -10.1027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5417   -9.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8536  -10.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1570  -10.0410    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 10  4  2  0
  9  1  1  6
  1  2  1  0
  2  3  1  0
  3  4  1  0
  9  5  1  0
  5  6  1  0
  3  6  1  0
  2  7  1  0
  3  8  1  1
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
  7 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  7  1  0
 27 28  2  0
 27 29  1  0
 24 27  1  0
 21 30  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2435076

   (1S,8R)-3-(2-bromophenyl)-8-methyl-12-(4-nitrophenyl)-4,9,10,11-tetraoxatricyclo[6.2.2.01,6]dodec-6-en-5-one

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: 474.26

Molecular Weight (Monoisotopic): 473.0110

AlogP: 4.46

#Rotatable Bonds: 3

Polar Surface Area: 97.13

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.54

CX LogD: 5.54

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: 0.77

References

1. Hossain MI, Świtalska M, Peng W, Takashima M, Wang N, Kaiser M, Wietrzyk J, Dan S, Yamori T, Inokuchi T..  (2013)  Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures.,  69  [PMID:24056020] [10.1016/j.ejmech.2013.08.008]

Source

Source(1):

• Scientific Literature