Mangostenone D

ID: ALA2437090

PubChem CID: 11696901

Max Phase: Preclinical

Molecular Formula: C23H24O6

Molecular Weight: 396.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCc1c(O)cc2oc3cc(O)c4c(c3c(=O)c2c1O)CCC(C)(C)O4

Standard InChI:  InChI=1S/C23H24O6/c1-11(2)5-6-12-14(24)9-17-19(20(12)26)21(27)18-13-7-8-23(3,4)29-22(13)15(25)10-16(18)28-17/h5,9-10,24-26H,6-8H2,1-4H3

Standard InChI Key:  VEUQWGPUUYXBDE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   39.5003   -8.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0919   -9.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9168   -9.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1144  -10.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1132  -11.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8282  -12.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8264  -10.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5419  -10.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5453  -11.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2606  -12.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2539  -10.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9739  -10.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9763  -11.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6905  -12.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3998  -11.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2493   -9.6998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3997  -10.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3982  -12.1878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8238   -9.7101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6851  -10.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9704  -10.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2558  -10.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9702   -9.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6815  -10.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3947  -10.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0974  -10.5151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3800   -9.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6710   -9.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1178  -12.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 24 12  1  0
 25 15  1  0
 11 16  2  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 24 25  2  0
 24 28  1  0
 25 26  1  0
 26  2  1  0
  2 27  1  0
 27 28  1  0
 15 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2437090

   5,9,11-Trihydroxy-3,3-dimethyl-10-(3-methylbut-2-enyl)-1,2-dihydropyrano[3,2-a]xanthen-12-one

Molecule Features

Natural Product: Yes

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: 396.44

Molecular Weight (Monoisotopic): 396.1573

AlogP: 4.68

#Rotatable Bonds: 2

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.27

CX Basic pKa: ┄

CX LogP: 5.45

CX LogD: 5.03

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 2.17

References

1. Azevedo CM, Afonso CM, Soares JX, Reis S, Sousa D, Lima RT, Vasconcelos MH, Pedro M, Barbosa J, Gales L, Pinto MM..  (2013)  Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models.,  69  [PMID:24113365] [10.1016/j.ejmech.2013.09.012]

Source

Source(1):

• Scientific Literature