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

ID: ALA138881

PubChem CID: 10548776

Max Phase: Preclinical

Molecular Formula: C24H28O5

Molecular Weight: 396.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H28O5/c1-14-12-18-19(23(3,4)13-24(5,6)29-18)15(2)20(14)28-22(26)17-10-8-16(9-11-17)21(25)27-7/h8-12H,13H2,1-7H3

Standard InChI Key:  IBIMEKCSFNNEJG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.3167   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -3.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -5.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4667   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -4.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9875   -3.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625   -2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -5.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -2.1250    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  6  1  0
  8  5  1  0
  9 11  2  0
 10  8  1  0
 11  5  1  0
 12 15  1  0
 13  4  1  0
 14  7  1  0
 15 20  2  0
 16  7  2  0
 17 12  2  0
 18 14  1  0
 19 14  2  0
 20 19  1  0
 21 18  2  0
 22 12  1  0
 23  4  1  0
 24  4  1  0
 25  3  1  0
 26  9  1  0
 27 10  1  0
 28 10  1  0
 29 22  1  0
 10 13  1  0
  2  9  1  0
 15 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA138881

   4-O-(2,2,4,4,5,7-hexamethyl-3H-chromen-6-yl) 1-O-methyl 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: 396.48

Molecular Weight (Monoisotopic): 396.1937

AlogP: 5.15

#Rotatable Bonds: 3

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.28

CX LogD: 6.28

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: 0.33

References

1. Zacheis D, Dhar A, Lu S, Madler MM, Klucik J, Brown CW, Liu S, Clement F, Subramanian S, Weerasekare GM, Berlin KD, Gold MA, Houck JR, Fountain KR, Benbrook DM..  (1999)  Heteroarotinoids inhibit head and neck cancer cell lines in vitro and in vivo through both RAR and RXR retinoic acid receptors.,  42  (21): [PMID:10543887] [10.1021/jm990292i]

Source

Source(1):

• Scientific Literature