(2'E)-1-(3,17beta-dihydroxy-1,3,5(10)-estratrienyl)-3'-(2''-chlorophenyl)prop-2'-en-1'-one

ID: ALA4546522

PubChem CID: 155552533

Max Phase: Preclinical

Molecular Formula: C27H29ClO3

Molecular Weight: 436.98

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4cc(C(=O)/C=C/c5ccccc5Cl)c(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C27H29ClO3/c1-27-13-12-18-19(22(27)9-11-26(27)31)8-6-17-14-25(30)21(15-20(17)18)24(29)10-7-16-4-2-3-5-23(16)28/h2-5,7,10,14-15,18-19,22,26,30-31H,6,8-9,11-13H2,1H3/b10-7+/t18-,19+,22-,26-,27-/m0/s1

Standard InChI Key:  ZGLFUZCSJUARIW-GTGLURLSSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   37.4885  -10.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4873  -11.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2001  -11.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1983  -10.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9117  -10.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9105  -11.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6253  -11.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3459  -11.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6277  -10.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3471  -10.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3575   -8.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6298   -9.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0769   -9.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0681  -10.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8568  -10.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3530   -9.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8710   -9.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7745  -11.7477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.1333   -8.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0715   -8.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3402   -9.6893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.0631  -10.9233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   39.6214  -10.9108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   36.7759  -10.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7757   -9.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0635  -10.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3509  -10.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6386  -10.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9265  -10.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2147  -10.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2145  -11.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9321  -11.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6410  -11.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9274   -9.2770    0.0000 Cl  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
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  2 18  1  0
 17 19  1  1
 13 20  1  1
 10 21  1  1
 14 22  1  6
  9 23  1  6
  1 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 29 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4546522

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 436.98

Molecular Weight (Monoisotopic): 436.1805

AlogP: 6.16

#Rotatable Bonds: 3

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.50

CX Basic pKa: ┄

CX LogP: 6.92

CX LogD: 6.67

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: 1.15

References

1. Wang C, Li L, Fu D, Qin T, Ran Y, Xu F, Du X, Gao H, Sun S, Yang T, Zhang X, Huo J, Zhao W, Zhang Z, Shi X..  (2019)  Discovery of chalcone-modified estradiol analogs as antitumour agents that Inhibit tumour angiogenesis and epithelial to mesenchymal transition.,  176  [PMID:31102934] [10.1016/j.ejmech.2019.04.071]

Source

Source(1):

• Scientific Literature