Toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester

ID: ALA3344403

PubChem CID: 118717762

Max Phase: Preclinical

Molecular Formula: C26H25NO3S

Molecular Weight: 431.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)OCCCn2ccc3c(/C=C/c4ccccc4)cccc32)cc1

Standard InChI:  InChI=1S/C26H25NO3S/c1-21-11-15-24(16-12-21)31(28,29)30-20-6-18-27-19-17-25-23(9-5-10-26(25)27)14-13-22-7-3-2-4-8-22/h2-5,7-17,19H,6,18,20H2,1H3/b14-13+

Standard InChI Key:  ZAHCTCYWUKEKPL-BUHFOSPRSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   10.4543  -22.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2467  -22.5801    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0363  -21.7865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7012  -25.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7001  -26.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4081  -26.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4063  -25.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1149  -25.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1152  -26.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8938  -26.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3749  -25.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8934  -25.2536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4103  -27.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037  -27.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7059  -28.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9978  -29.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9996  -30.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7089  -30.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4179  -30.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4126  -29.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1457  -24.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9450  -24.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1972  -23.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9965  -23.3587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0480  -22.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5930  -23.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3916  -22.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6445  -22.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0927  -21.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2962  -21.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4436  -21.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3344403

   ---

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: 431.56

Molecular Weight (Monoisotopic): 431.1555

AlogP: 5.92

#Rotatable Bonds: 8

Polar Surface Area: 48.30

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.57

CX LogD: 6.57

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.20

Np Likeness Score: -0.91

References

1. Ferla S, Gomaa MS, Brancale A, Zhu J, Ochalek JT, DeLuca HF, Simons C..  (2014)  Novel styryl-indoles as small molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): Synthesis and biological evaluation.,  87  [PMID:25240094] [10.1016/j.ejmech.2014.09.035]

2. Bruno, Robert D RD and Njar, Vincent C O VC.  2007-08-01  Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.  [PMID:17544277]

3. Taban, Ismail M IM, Zhu, Jinge J, DeLuca, Hector F HF and Simons, Claire C.  2017-08-01  Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides.  [PMID:28601511]

Source

Source(1):

• Scientific Literature