1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole

ID: ALA3344393

PubChem CID: 118717752

Max Phase: Preclinical

Molecular Formula: C24H25N3O2

Molecular Weight: 387.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/c2cccc3c2ccn3CCCn2ccnc2)cc(OC)c1

Standard InChI:  InChI=1S/C24H25N3O2/c1-28-21-15-19(16-22(17-21)29-2)7-8-20-5-3-6-24-23(20)9-13-27(24)12-4-11-26-14-10-25-18-26/h3,5-10,13-18H,4,11-12H2,1-2H3/b8-7+

Standard InChI Key:  JNCMZCZFSIAVQJ-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

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    7.0633   -4.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7713   -4.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7695   -2.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4781   -3.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4784   -4.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2570   -4.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7381   -3.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2566   -2.9955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7735   -5.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669   -5.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0691   -6.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3610   -6.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628   -7.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0721   -8.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7811   -7.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7758   -6.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5089   -2.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3082   -2.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -1.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3597   -1.1006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9656   -1.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6775   -1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5013   -0.4376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6934   -0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6560   -8.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474   -7.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4913   -8.1480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4964   -8.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 21  1  0
 14 26  1  0
 26 27  1  0
 16 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3344393

   ---

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: 387.48

Molecular Weight (Monoisotopic): 387.1947

AlogP: 5.12

#Rotatable Bonds: 8

Polar Surface Area: 41.21

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.53

CX LogP: 4.29

CX LogD: 4.25

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -1.01

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]

Source

Source(1):

• Scientific Literature