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

ID: ALA342569

PubChem CID: 10892273

Max Phase: Preclinical

Molecular Formula: C18H14O5

Molecular Weight: 310.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1Cc2c(ccc3c(=O)c4cccc(CC(=O)O)c4oc23)O1

Standard InChI:  InChI=1S/C18H14O5/c1-9-7-13-14(22-9)6-5-12-16(21)11-4-2-3-10(8-15(19)20)17(11)23-18(12)13/h2-6,9H,7-8H2,1H3,(H,19,20)

Standard InChI Key:  CGNNXSGBFTXFDV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  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
    0.1042   -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
   -0.8875   -2.5917    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
  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  2  1  0
 12  5  1  0
 13 14  1  0
 14 10  1  0
 15  4  2  0
 16  8  1  0
 17 12  1  0
 18 13  2  0
 19  7  1  0
 20 13  1  0
 21 10  2  0
 22 21  1  0
 23 17  1  0
 17  9  1  0
 16 11  2  0
  4  7  1  0
 19 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA342569

   2-(2-Methyl-6-oxo-1,2-dihydrofuro[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: 310.31

Molecular Weight (Monoisotopic): 310.0841

AlogP: 2.90

#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: 3.21

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: -0.55

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: 0.85

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