(E)-4-(4-Nonylphenyl)-4-oxobut-2-enoic Acid

ID: ALA5181434

PubChem CID: 168272357

Max Phase: Preclinical

Molecular Formula: C19H26O3

Molecular Weight: 302.41

Names and Identifiers

Canonical SMILES:  CCCCCCCCCc1ccc(C(=O)/C=C/C(=O)O)cc1

Standard InChI:  InChI=1S/C19H26O3/c1-2-3-4-5-6-7-8-9-16-10-12-17(13-11-16)18(20)14-15-19(21)22/h10-15H,2-9H2,1H3,(H,21,22)/b15-14+

Standard InChI Key:  IYOLTUMKGMSVMI-CCEZHUSRSA-N

Molfile:  

 
     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   -0.7131    2.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    2.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    1.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    1.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279    2.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279    3.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    2.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2864    2.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718    1.6522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    1.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -2.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -3.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864   -3.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5181434

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 302.41

Molecular Weight (Monoisotopic): 302.1882

AlogP: 4.80

#Rotatable Bonds: 11

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.26

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 2.35

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.36

Np Likeness Score: 0.28

References

1. Kudo Y, Endo S, Fujita M, Ota A, Kamatari YO, Tanaka Y, Ishikawa T, Ikeda H, Okada T, Toyooka N, Fujimoto N, Matsunaga T, Ikari A..  (2022)  Discovery and Structure-Based Optimization of Novel Atg4B Inhibitors for the Treatment of Castration-Resistant Prostate Cancer.,  65  (6.0): [PMID:35244402] [10.1021/acs.jmedchem.1c02113]

Source

Source(1):

• Scientific Literature