(E)-3-[4-((Z)-1,2-Diphenyl-but-1-enyl)-phenyl]-N-ethyl-acrylamide

ID: ALA38776

PubChem CID: 9951881

Max Phase: Preclinical

Molecular Formula: C27H27NO

Molecular Weight: 381.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)/C=C/c1ccc(/C(=C(/CC)c2ccccc2)c2ccccc2)cc1

Standard InChI:  InChI=1S/C27H27NO/c1-3-25(22-11-7-5-8-12-22)27(23-13-9-6-10-14-23)24-18-15-21(16-19-24)17-20-26(29)28-4-2/h5-20H,3-4H2,1-2H3,(H,28,29)/b20-17+,27-25-

Standard InChI Key:  BRMNLIQZGXBZHN-VDFPVXJCSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    4.2500   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -4.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292    0.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -3.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542    0.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -5.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -4.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -5.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  4  1  0
  4  6  2  0
  5  1  1  0
  6 13  1  0
  7  1  1  0
  8  2  1  0
  9  3  2  0
 10  5  1  0
 11  5  2  0
 12  3  1  0
 13 15  2  0
 14 10  2  0
 15 11  1  0
 16  2  1  0
 17  7  2  0
 18  8  2  0
 19  8  1  0
 20  7  1  0
 21 12  1  0
 22 16  1  0
 23 21  1  0
 24 20  2  0
 25 18  1  0
 26 19  2  0
 27 17  1  0
 28 24  1  0
 29 26  1  0
 14 13  1  0
 27 28  2  0
 25 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA38776

   (E)-3-[4-[(Z)-1,2-diphenylbut-1-enyl]phenyl]-N-ethylprop-2-enamide

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: 381.52

Molecular Weight (Monoisotopic): 381.2093

AlogP: 6.21

#Rotatable Bonds: 7

Polar Surface Area: 29.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.43

CX LogD: 6.43

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.11

References

1. Willson TM, Henke BR, Momtahen TM, Charifson PS, Batchelor KW, Lubahn DB, Moore LB, Oliver BB, Sauls HR, Triantafillou JA..  (1994)  3-[4-(1,2-Diphenylbut-1-enyl)phenyl]acrylic acid: a non-steroidal estrogen with functional selectivity for bone over uterus in rats.,  37  (11): [PMID:8201587] [10.1021/jm00037a002]

Source

Source(1):

• Scientific Literature