5-(2-Fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrrole-2-carbonitrile

ID: ALA4095883

PubChem CID: 132471744

Max Phase: Preclinical

Molecular Formula: C12H9FN2O

Molecular Weight: 216.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(C#N)ccc1-c1ccc(O)cc1F

Standard InChI:  InChI=1S/C12H9FN2O/c1-15-8(7-14)2-5-12(15)10-4-3-9(16)6-11(10)13/h2-6,16H,1H3

Standard InChI Key:  WVKAVGHFAICIIO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   16.0001  -16.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6764  -16.6640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3230  -16.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0450  -15.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2292  -15.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1052  -16.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2987  -17.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0825  -17.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6735  -16.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4755  -16.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6920  -15.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2286  -16.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4596  -16.7593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4585  -17.0747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7018  -17.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4954  -15.0321    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3  6  1  0
 12 13  3  0
  1 12  1  0
  9 14  1  0
  2 15  1  0
 11 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095883

   ---

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: 216.21

Molecular Weight (Monoisotopic): 216.0699

AlogP: 2.41

#Rotatable Bonds: 1

Polar Surface Area: 48.95

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.43

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: 2.42

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.80

Np Likeness Score: -0.58

References

1. Unwalla R, Mousseau JJ, Fadeyi OO, Choi C, Parris K, Hu B, Kenney T, Chippari S, McNally C, Vishwanathan K, Kilbourne E, Thompson C, Nagpal S, Wrobel J, Yudt M, Morris CA, Powell D, Gilbert AM, Chekler ELP..  (2017)  Structure-Based Approach To Identify 5-[4-Hydroxyphenyl]pyrrole-2-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators.,  60  (14): [PMID:28696695] [10.1021/acs.jmedchem.7b00373]

Source

Source(1):

• Scientific Literature