(E)-2-cyano-3-(4-(dipentylamino)-2-methoxyphenyl)acrylic acid

ID: ALA3582421

PubChem CID: 71667549

Max Phase: Preclinical

Molecular Formula: C21H30N2O3

Molecular Weight: 358.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCN(CCCCC)c1ccc(/C=C(\C#N)C(=O)O)c(OC)c1

Standard InChI:  InChI=1S/C21H30N2O3/c1-4-6-8-12-23(13-9-7-5-2)19-11-10-17(20(15-19)26-3)14-18(16-22)21(24)25/h10-11,14-15H,4-9,12-13H2,1-3H3,(H,24,25)/b18-14+

Standard InChI Key:  LYZWLUWMPJZUDU-NBVRZTHBSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    5.1877   -7.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999   -0.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1972   -1.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4998   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7972   -1.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8387   -0.9251    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
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948    3.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2551    4.3525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    3.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895    4.9584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9334    3.1614    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
   -2.5972   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.7031    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  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  3  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 15 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582421

   (E)-2-cyano-3-[4-(dipentylamino)-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: 358.48

Molecular Weight (Monoisotopic): 358.2256

AlogP: 4.87

#Rotatable Bonds: 12

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: 2.12

CX Basic pKa: 4.96

CX LogP: 3.24

CX LogD: 1.94

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: -0.60

References

1. Gurrapu S, Jonnalagadda SK, Alam MA, Nelson GL, Sneve MG, Drewes LR, Mereddy VR..  (2015)  Monocarboxylate transporter 1 inhibitors as potential anticancer agents.,  6  (5): [PMID:26005533] [10.1021/acsmedchemlett.5b00049]

2.  (2016)  Therapeutic compounds, 

3. 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