Terephthalic acid 1-methyl ester 4-(4,4,5,7-tetramethyl-2-oxo-chroman-6-yl) ester

ID: ALA332466

PubChem CID: 10786125

Max Phase: Preclinical

Molecular Formula: C22H22O6

Molecular Weight: 382.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(C(=O)Oc2c(C)cc3c(c2C)C(C)(C)CC(=O)O3)cc1

Standard InChI:  InChI=1S/C22H22O6/c1-12-10-16-18(22(3,4)11-17(23)27-16)13(2)19(12)28-21(25)15-8-6-14(7-9-15)20(24)26-5/h6-10H,11H2,1-5H3

Standard InChI Key:  BJCCGXAOODPTTH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4042  -11.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875  -11.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542  -11.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750  -12.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167  -11.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667  -13.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292  -11.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417  -12.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042  -12.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875  -13.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792  -10.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417  -11.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417  -11.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667  -10.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292  -12.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2542  -11.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375  -10.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500  -10.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667  -11.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4000  -10.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417  -10.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667  -10.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792  -10.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167  -13.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042  -10.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  1  1  0
  4  1  1  0
  5  1  2  0
  6  2  1  0
  7  5  1  0
  8  6  1  0
  9  7  1  0
 10 11  2  0
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 13  4  1  0
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 15 21  1  0
 16  8  2  0
 17  9  2  0
 18 12  2  0
 19 14  2  0
 20 14  1  0
 21 20  2  0
 22 19  1  0
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 26  3  1  0
 27 10  1  0
 28 23  1  0
 13  9  1  0
  2 10  1  0
 22 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA332466

   1-O-methyl 4-O-(4,4,5,7-tetramethyl-2-oxo-3H-chromen-6-yl) benzene-1,4-dicarboxylate

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: 382.41

Molecular Weight (Monoisotopic): 382.1416

AlogP: 3.90

#Rotatable Bonds: 3

Polar Surface Area: 78.90

Molecular Species: ┄

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.16

CX LogD: 5.16

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: 0.33

References

1. Benbrook DM, Madler MM, Spruce LW, Birckbichler PJ, Nelson EC, Subramanian S, Weerasekare GM, Gale JB, Patterson MK, Wang B, Wang W, Lu S, Rowland TC, DiSivestro P, Lindamood C, Hill DL, Berlin KD..  (1997)  Biologically active heteroarotinoids exhibiting anticancer activity and decreased toxicity.,  40  (22): [PMID:9357524] [10.1021/jm970196m]

Source

Source(1):

• Scientific Literature