(3,3-Dimethyl-7-oxo-3H,7H-4,12-dioxa-benzo[a]anthracen-11-yl)-acetic acid

ID: ALA359026

PubChem CID: 11024161

Max Phase: Preclinical

Molecular Formula: C20H16O5

Molecular Weight: 336.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H16O5/c1-20(2)9-8-12-15(25-20)7-6-14-17(23)13-5-3-4-11(10-16(21)22)18(13)24-19(12)14/h3-9H,10H2,1-2H3,(H,21,22)

Standard InChI Key:  HCCZIOIGYVKMAZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  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
    2.2375   -1.2917    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   -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
    0.1167   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -1.7042    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
   -0.6000   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -2.5292    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
   -2.1208   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -3.2417    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  3  1  0
  6  1  1  0
  7  5  2  0
  8  6  2  0
  9  6  1  0
 10  8  1  0
 11  5  1  0
 12  2  1  0
 13  9  2  0
 14 13  1  0
 15 16  1  0
 16 11  1  0
 17  4  2  0
 18  8  1  0
 19 15  2  0
 20  7  1  0
 21 15  1  0
 22 11  2  0
 23 22  1  0
 24 14  1  0
 25 14  1  0
 18 12  2  0
  4  7  1  0
 14 10  1  0
 20 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA359026

   2-(3,3-Dimethyl-7-oxopyrano[2,3-c]xanthen-11-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: 336.34

Molecular Weight (Monoisotopic): 336.0998

AlogP: 3.76

#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: 3.20

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 0.05

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: 1.63

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