(5-Methyl-9-oxo-6-prop-2-ynyloxy-9H-xanthen-4-yl)-acetic acid methyl ester

ID: ALA148123

PubChem CID: 44363896

Max Phase: Preclinical

Molecular Formula: C20H16O5

Molecular Weight: 336.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOc1ccc2c(=O)c3cccc(CC(=O)OC)c3oc2c1C

Standard InChI:  InChI=1S/C20H16O5/c1-4-10-24-16-9-8-15-18(22)14-7-5-6-13(11-17(21)23-3)20(14)25-19(15)12(16)2/h1,5-9H,10-11H2,2-3H3

Standard InChI Key:  WDYGJWKYBYMQII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.0000   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -2.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2833   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042    0.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -2.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -4.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375   -2.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -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 22  1  0
 11 10  3  0
 12 14  1  0
 13  7  2  0
 14  8  1  0
 15  4  2  0
 16 13  1  0
 17 12  2  0
 18  6  1  0
 19 12  1  0
 20 13  1  0
 21  7  1  0
 22 20  1  0
 23  8  2  0
 24 23  1  0
 25 19  1  0
 16  9  2  0
  4  6  1  0
 18 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA148123

   Methyl 2-(5-methyl-9-oxo-6-prop-2-ynoxyxanthen-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: 336.34

Molecular Weight (Monoisotopic): 336.0998

AlogP: 2.98

#Rotatable Bonds: 4

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: 3.33

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.42

Np Likeness Score: -0.22

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