Toluene-4-sulfonic acid 3-{4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1-yl}-propyl ester

ID: ALA3344404

PubChem CID: 118717763

Max Phase: Preclinical

Molecular Formula: C28H29NO5S

Molecular Weight: 491.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/c2cccc3c2ccn3CCCOS(=O)(=O)c2ccc(C)cc2)cc(OC)c1

Standard InChI:  InChI=1S/C28H29NO5S/c1-21-8-12-26(13-9-21)35(30,31)34-17-5-15-29-16-14-27-23(6-4-7-28(27)29)11-10-22-18-24(32-2)20-25(19-22)33-3/h4,6-14,16,18-20H,5,15,17H2,1-3H3/b11-10+

Standard InChI Key:  RSTCRUIYHKRMAK-ZHACJKMWSA-N

Molfile:  

     RDKit          2D

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   18.9687  -22.6502    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.7584  -21.8567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4232  -25.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4221  -26.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.7185  -23.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.3666  -22.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8148  -21.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.8502  -30.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8552  -31.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0148  -30.4897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0166  -31.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 17 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3344404

   ---

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: 491.61

Molecular Weight (Monoisotopic): 491.1766

AlogP: 5.93

#Rotatable Bonds: 10

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.25

CX LogD: 6.25

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.16

Np Likeness Score: -0.80

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