(6-Allyloxy-5-methyl-9-oxo-9H-xanthen-4-yl)-acetic acid

ID: ALA341629

PubChem CID: 44363893

Max Phase: Preclinical

Molecular Formula: C19H16O5

Molecular Weight: 324.33

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  SHMYKBWLSQUOCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.1167   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -2.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -3.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292    0.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -3.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -4.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -2.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -1.9542    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 12  1  0
 11  7  2  0
 12  8  1  0
 13  4  2  0
 14 11  1  0
 15 10  2  0
 16 24  1  0
 17 16  2  0
 18  6  1  0
 19 10  1  0
 20 11  1  0
 21  7  1  0
 22  8  2  0
 23 22  1  0
 24 20  1  0
 14  9  2  0
  4  6  1  0
 18 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA341629

   2-(5-Methyl-9-oxo-6-prop-2-enoxyxanthen-4-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: 3.45

#Rotatable Bonds: 5

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: 3.23

CX Basic pKa: ┄

CX LogP: 3.68

CX LogD: 0.24

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: 0.19

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