4,4-Dimethyl-chroman-6-carboxylic acid 4-ethoxycarbonyl-phenyl ester

ID: ALA122529

PubChem CID: 10831967

Max Phase: Preclinical

Molecular Formula: C21H22O5

Molecular Weight: 354.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(OC(=O)c2ccc3c(c2)C(C)(C)CCO3)cc1

Standard InChI:  InChI=1S/C21H22O5/c1-4-24-19(22)14-5-8-16(9-6-14)26-20(23)15-7-10-18-17(13-15)21(2,3)11-12-25-18/h5-10,13H,4,11-12H2,1-3H3

Standard InChI Key:  GFCMLNHBCJGEJM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    1.9667   -7.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -6.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -6.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -7.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -6.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -7.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -8.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -8.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -6.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -4.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -8.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -8.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -6.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4000   -6.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375   -6.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -7.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -8.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -7.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -5.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8250   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  3  2  0
  5  9  1  0
  6  1  1  0
  7  2  1  0
  8  1  2  0
  9 15  2  0
 10  8  1  0
 11  2  2  0
 12  5  2  0
 13 14  2  0
 14  8  1  0
 15 20  1  0
 16 19  2  0
 17  7  1  0
 18  5  1  0
 19 17  1  0
 20 17  2  0
 21 10  1  0
 22  6  1  0
 23  6  1  0
 24  6  1  0
 25 18  1  0
 26 25  1  0
 22 21  1  0
  4 13  1  0
  9 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA122529

   (4-Ethoxycarbonylphenyl) 4,4-dimethyl-2,3-dihydrochromene-6-carboxylate

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: 354.40

Molecular Weight (Monoisotopic): 354.1467

AlogP: 4.14

#Rotatable Bonds: 4

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 4.91

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -0.04

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]

2. 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