(3S,3a'R,5a'S,9b'S)-3-(4-bromophenyl)-5a',9'-dimethyl-2-phenyl-3a',4',5',5a'-tetrahydro-2'H-spiro[isoxazolidine-5,3'-naphtho[1,2-b]furan]-2',8'(9b'H)-dione

ID: ALA2375835

PubChem CID: 73353361

Max Phase: Preclinical

Molecular Formula: C28H26BrNO4

Molecular Weight: 520.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2[C@H]3OC(=O)C4(C[C@@H](c5ccc(Br)cc5)N(c5ccccc5)O4)[C@@H]3CC[C@@]2(C)C=CC1=O

Standard InChI:  InChI=1S/C28H26BrNO4/c1-17-23(31)13-15-27(2)14-12-21-25(24(17)27)33-26(32)28(21)16-22(18-8-10-19(29)11-9-18)30(34-28)20-6-4-3-5-7-20/h3-11,13,15,21-22,25H,12,14,16H2,1-2H3/t21-,22+,25+,27+,28?/m1/s1

Standard InChI Key:  AODICUCFAVBLJG-RDCCRBAQSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
   13.5366   -4.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1194   -4.7942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8538   -4.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7251   -3.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9109   -3.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0671   -2.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0671   -3.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7828   -4.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7828   -2.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4943   -2.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4958   -3.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9237   -2.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2067   -2.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3528   -4.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4872   -2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9253   -3.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2053   -4.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3748   -4.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1970   -4.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7824   -4.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6071   -5.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6405   -3.2388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6220   -4.6491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1659   -2.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9906   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4286   -2.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0431   -1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2150   -1.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7808   -2.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5841   -4.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6257   -5.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3590   -5.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0514   -5.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0055   -4.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2718   -4.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4802   -0.8163    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  6  9  2  0
  7  8  1  0
  8 11  2  0
 10  9  1  0
 10 11  1  0
 10 13  1  0
 11 17  1  0
 16 12  1  0
 12 13  1  0
  7 14  2  0
 10 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  1  1  0
 16  1  1  0
  8 20  1  0
 19 21  2  0
 16 22  1  6
 17 23  1  1
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  4 24  1  1
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
  3 30  1  0
 27 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2375835

   (3S,3'aR,5'aS,9'bS)-3-(4-bromophenyl)-5'a,9'-dimethyl-2-phenylspiro[1,2-oxazolidine-5,3'-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran]-2',8'-dione

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: 520.42

Molecular Weight (Monoisotopic): 519.1045

AlogP: 5.87

#Rotatable Bonds: 2

Polar Surface Area: 55.84

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.35

CX LogD: 6.35

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: 1.11

References

1. Khazir J, Singh PP, Reddy DM, Hyder I, Shafi S, Sawant SD, Chashoo G, Mahajan A, Alam MS, Saxena AK, Arvinda S, Gupta BD, Kumar HM..  (2013)  Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin.,  63  [PMID:23501113] [10.1016/j.ejmech.2013.01.003]

Source

Source(1):

• Scientific Literature