N-(2,2,4,4-Tetramethyl-thiochroman-6-yl)-terephthalamic acid methyl ester

ID: ALA139536

PubChem CID: 11740691

Max Phase: Preclinical

Molecular Formula: C22H25NO3S

Molecular Weight: 383.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(C(=O)Nc2ccc3c(c2)C(C)(C)CC(C)(C)S3)cc1

Standard InChI:  InChI=1S/C22H25NO3S/c1-21(2)13-22(3,4)27-18-11-10-16(12-17(18)21)23-19(24)14-6-8-15(9-7-14)20(25)26-5/h6-12H,13H2,1-5H3,(H,23,24)

Standard InChI Key:  JZHWLPKXASYCHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.8042   -5.1417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -4.8375    0.0000 C   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
    2.2875   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -3.9292    0.0000 N   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   -4.2417    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
    3.8375   -3.9375    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
    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
    3.8375   -5.1292    0.0000 C   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
    4.3542   -4.8292    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
    2.2792   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -3.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -4.8375    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  4  2  0
  3  9  1  0
  4  1  1  0
  5  7  1  0
  6  1  1  0
  7 13  1  0
  8 11  1  0
  9  6  1  0
 10  5  1  0
 11 19  2  0
 12  2  1  0
 13 21  1  0
 14  5  2  0
 15  8  2  0
 16  4  1  0
 17 10  1  0
 18 10  2  0
 19 18  1  0
 20 17  2  0
 21 16  2  0
 22  8  1  0
 23  3  1  0
 24  3  1  0
 25  6  1  0
 26  6  1  0
 27 22  1  0
  2  3  1  0
 13 12  2  0
 20 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA139536

   N-(2,2,4,4-Tetramethyl-thiochroman-6-yl)-terephthalamic acid methyl ester

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: 383.51

Molecular Weight (Monoisotopic): 383.1555

AlogP: 5.28

#Rotatable Bonds: 3

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.65

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