(5-(3-chloro-4-hydroxy-5-(piperazin-1-ylmethyl)phenyl)thiophen-2-yl)(2,6-difluoro-3-hydroxyphenyl)methanone

ID: ALA4091053

PubChem CID: 122652942

Max Phase: Preclinical

Molecular Formula: C23H21ClF2N2O3S

Molecular Weight: 478.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(Cl)cc(-c2ccc(C(=O)c3c(F)ccc(O)c3F)s2)cc1CN1CCNCC1

Standard InChI:  InChI=1S/C23H21ClF2N2O3S/c1-31-23-14(12-28-8-6-27-7-9-28)10-13(11-15(23)24)18-4-5-19(32-18)22(30)20-16(25)2-3-17(29)21(20)26/h2-5,10-11,27,29H,6-9,12H2,1H3

Standard InChI Key:  WACSLJSCYBMPMF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   32.7164  -19.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5414  -19.3748    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.7982  -18.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1289  -18.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4638  -18.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5793  -18.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1916  -18.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9760  -18.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1492  -17.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5320  -17.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7500  -17.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2306  -20.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4103  -19.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5652  -20.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0776  -21.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4115  -22.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2327  -22.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7189  -21.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3822  -20.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9254  -22.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2573  -21.3743    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.8661  -20.2130    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.5880  -19.1900    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   36.9338  -17.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7018  -16.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4858  -16.2116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0981  -16.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8794  -16.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0533  -15.7069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4397  -15.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6520  -15.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5172  -18.1579    0.0000 C   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
  1 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
 15 21  1  0
 19 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 25 26  1  0
 26 27  1  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 24 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091053

   ---

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: 478.95

Molecular Weight (Monoisotopic): 478.0929

AlogP: 4.70

#Rotatable Bonds: 6

Polar Surface Area: 61.80

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.71

CX Basic pKa: 9.23

CX LogP: 3.71

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.90

References

1. Abdelsamie AS, van Koppen CJ, Bey E, Salah M, Börger C, Siebenbürger L, Laschke MW, Menger MD, Frotscher M..  (2017)  Treatment of estrogen-dependent diseases: Design, synthesis and profiling of a selective 17β-HSD1 inhibitor with sub-nanomolar IC50 for a proof-of-principle study.,  127  [PMID:27852458] [10.1016/j.ejmech.2016.11.004]

Source

Source(1):

• Scientific Literature