US9296728, 19

ID: ALA3892299

PubChem CID: 71667553

Max Phase: Preclinical

Molecular Formula: C25H22N2O3

Molecular Weight: 398.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N(Cc2ccccc2)Cc2ccccc2)ccc1/C=C(\C#N)C(=O)O

Standard InChI:  InChI=1S/C25H22N2O3/c1-30-24-15-23(13-12-21(24)14-22(16-26)25(28)29)27(17-19-8-4-2-5-9-19)18-20-10-6-3-7-11-20/h2-15H,17-18H2,1H3,(H,28,29)/b22-14+

Standard InChI Key:  VOPFDHPGYLVCCO-HYARGMPZSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.6387   -0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6418   -2.3971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3494   -5.8476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711   -5.8532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6020    2.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034    3.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2002    2.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1955    1.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8942    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2969    3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979    3.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8973    3.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1961    3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955    1.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962    0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5975    1.5042    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  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  3  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3892299

   (E)-2-cyano-3-[4-(dibenzylamino)-2-methoxyphenyl]prop-2-enoic acid

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: 398.46

Molecular Weight (Monoisotopic): 398.1630

AlogP: 4.89

#Rotatable Bonds: 8

Polar Surface Area: 73.56

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.57

CX Basic pKa: 1.37

CX LogP: 4.90

CX LogD: 1.83

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -0.66

References

1.  (2016)  Therapeutic compounds, 

2. Puri S, Juvale K..  (2020)  Monocarboxylate transporter 1 and 4 inhibitors as potential therapeutics for treating solid tumours: A review with structure-activity relationship insights.,  199  [PMID:32388280] [10.1016/j.ejmech.2020.112393]

Source

Source(2):

• Scientific Literature
• BindingDB Database