x[5-Methyl-6-(2-methyl-allyloxy)-9-oxo-9H-xanthen-4-yl]-acetic acid methyl ester

ID: ALA147376

PubChem CID: 44363885

Max Phase: Preclinical

Molecular Formula: C21H20O5

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)COc1ccc2c(=O)c3cccc(CC(=O)OC)c3oc2c1C

Standard InChI:  InChI=1S/C21H20O5/c1-12(2)11-25-17-9-8-16-19(23)15-7-5-6-14(10-18(22)24-4)21(15)26-20(16)13(17)3/h5-9H,1,10-11H2,2-4H3

Standard InChI Key:  PJDYIGQWQQFMLI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.7667   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -2.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792    0.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -2.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -2.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -4.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -4.6125    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  5  2  0
  7  1  1  0
  8  5  1  0
  9  2  1  0
 10  7  2  0
 11 12  1  0
 12  8  1  0
 13  4  2  0
 14 10  1  0
 15 10  1  0
 16 19  1  0
 17 11  2  0
 18 16  2  0
 19 14  1  0
 20  6  1  0
 21 11  1  0
 22  7  1  0
 23  8  2  0
 24 23  1  0
 25 16  1  0
 26 21  1  0
 15  9  2  0
  4  6  1  0
 20 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA147376

   Methyl 2-[5-methyl-6-(2-methylprop-2-enoxy)-9-oxoxanthen-4-yl]acetate

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: 352.39

Molecular Weight (Monoisotopic): 352.1311

AlogP: 3.93

#Rotatable Bonds: 5

Polar Surface Area: 65.74

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -0.02

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