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

ID: ALA147572

PubChem CID: 44363924

Max Phase: Preclinical

Molecular Formula: C22H22O5

Molecular Weight: 366.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Cc1cccc2c(=O)c3ccc(OCC=C(C)C)c(C)c3oc12

Standard InChI:  InChI=1S/C22H22O5/c1-13(2)10-11-26-18-9-8-17-20(24)16-7-5-6-15(12-19(23)25-4)22(16)27-21(17)14(18)3/h5-10H,11-12H2,1-4H3

Standard InChI Key:  OJTAPMZDJWQOHJ-UHFFFAOYSA-N

Molfile:  

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   10.7625   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4667   -2.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4667   -0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1792   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0542   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3417   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8917   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3375   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3167   -2.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6250   -2.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6042   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0542   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6042   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6042   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3167   -4.5500    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
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  9  2  1  0
 10 12  1  0
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 20 19  1  0
 21 10  1  0
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 24 23  1  0
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 27 21  1  0
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  4  6  1  0
 18 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA147572

   Methyl 2-[5-methyl-6-(3-methylbut-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: 366.41

Molecular Weight (Monoisotopic): 366.1467

AlogP: 4.32

#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: 4.46

CX LogD: 4.46

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: 0.56

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