(2,2-Dimethyl-6-oxo-1,2-dihydro-6H-3,11-dioxa-cyclopenta[a]anthracen-10-yl)-acetic acid

ID: ALA146290

PubChem CID: 11001852

Max Phase: Preclinical

Molecular Formula: C19H16O5

Molecular Weight: 324.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Cc2c(ccc3c(=O)c4cccc(CC(=O)O)c4oc23)O1

Standard InChI:  InChI=1S/C19H16O5/c1-19(2)9-13-14(24-19)7-6-12-16(22)11-5-3-4-10(8-15(20)21)17(11)23-18(12)13/h3-7H,8-9H2,1-2H3,(H,20,21)

Standard InChI Key:  LMADYIUNBZGEDA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    0.8167   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -1.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250    0.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -2.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -3.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  1  1  0
  6  3  1  0
  7  6  2  0
  8  5  2  0
  9  8  1  0
 10  6  1  0
 11 13  1  0
 12  2  1  0
 13  5  1  0
 14 15  1  0
 15 10  1  0
 16  4  2  0
 17  8  1  0
 18 14  2  0
 19  7  1  0
 20 14  1  0
 21 10  2  0
 22 21  1  0
 23 11  1  0
 24 11  1  0
 11  9  1  0
 17 12  2  0
  4  7  1  0
 19 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA146290

   2-(2,2-dimethyl-6-oxo-1H-furo[2,3-c]xanthen-10-yl)acetic acid

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: 324.33

Molecular Weight (Monoisotopic): 324.0998

AlogP: 3.29

#Rotatable Bonds: 2

Polar Surface Area: 76.74

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: 3.18

CX LogD: -0.27

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: 0.74

References

1. Gobbi S, Rampa A, Bisi A, Belluti F, Valenti P, Caputo A, Zampiron A, Carrara M..  (2002)  Synthesis and antitumor activity of new derivatives of xanthen-9-one-4-acetic acid.,  45  (22): [PMID:12383019] [10.1021/jm020929p]

Source

Source(1):

• Scientific Literature