(+/-)-6a,12a-Dihydro-6H-5,8,10,12-tetraoxa-benzo[a]cyclopenta[h]fluorene-3,4-dione

ID: ALA476857

PubChem CID: 25267867

Max Phase: Preclinical

Molecular Formula: C16H10O6

Molecular Weight: 298.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=CC2=C(OC[C@@H]3c4cc5c(cc4O[C@H]23)OCO5)C1=O

Standard InChI:  InChI=1S/C16H10O6/c17-10-2-1-7-15-9(5-19-16(7)14(10)18)8-3-12-13(21-6-20-12)4-11(8)22-15/h1-4,9,15H,5-6H2/t9-,15-/m1/s1

Standard InChI Key:  QQOGWHMQKKWDGX-RFAUZJTJSA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   14.0319   -3.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0307   -4.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7456   -5.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7438   -3.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4591   -3.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4580   -4.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8908   -3.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1733   -3.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8896   -4.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1712   -5.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3401   -5.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5025   -5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1612   -6.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6410   -6.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3193   -5.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3173   -3.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7413   -2.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6000   -4.2792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.4542   -5.5167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8012   -5.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4659   -6.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0784   -7.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7924   -6.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6209   -5.9240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
 12  9  1  0
  2  3  2  0
 12 13  2  0
  3  6  1  0
 13 14  1  0
 14 21  2  0
  1  2  1  0
 20 15  2  0
 15 12  1  0
  5  8  1  0
  1 16  2  0
  6 10  1  0
  4 17  2  0
  9  7  1  0
  9 18  1  1
  7  8  1  0
 10 19  1  1
 20 21  1  0
  9 10  1  0
  5  4  1  0
  4  1  1  0
  5  6  2  0
 10 11  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA476857

   (1S,12S)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14-pentaene-16,17-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: 298.25

Molecular Weight (Monoisotopic): 298.0477

AlogP: 1.25

#Rotatable Bonds: ┄

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: 1.86

References

1. Netto CD, Santos ES, Castro CP, da Silva AJ, Rumjanek VM, Costa PR..  (2009)  (+/-)-3,4-Dihydroxy-8,9-methylenedioxypterocarpan and derivatives: cytotoxic effect on human leukemia cell lines.,  44  (2): [PMID:18468732] [10.1016/j.ejmech.2008.01.027]

Source

Source(1):

• Scientific Literature