[5-Methyl-6-(3-methyl-but-2-enyloxy)-9-oxo-9H-xanthen-4-yl]-acetic acid

ID: ALA147547

PubChem CID: 44363897

Max Phase: Preclinical

Molecular Formula: C21H20O5

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H20O5/c1-12(2)9-10-25-17-8-7-16-19(24)15-6-4-5-14(11-18(22)23)21(15)26-20(16)13(17)3/h4-9H,10-11H2,1-3H3,(H,22,23)

Standard InChI Key:  KVNROQALSFXJDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.1875   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -2.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -3.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -4.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -2.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083   -2.3417    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 17  2  0
 17 21  1  0
 18  6  1  0
 19 10  1  0
 20 11  1  0
 21 20  1  0
 22  7  1  0
 23  8  2  0
 24 23  1  0
 25 16  1  0
 26 16  1  0
 14  9  2  0
  4  6  1  0
 18 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA147547

   2-[5-Methyl-6-(3-methylbut-2-enoxy)-9-oxoxanthen-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: 352.39

Molecular Weight (Monoisotopic): 352.1311

AlogP: 4.23

#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: 4.31

CX LogD: 0.87

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: 0.64

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