2-cyano-3-(2-methoxy-4-(piperidin-1-yl)phenyl)acrylic acid

ID: ALA3582501

PubChem CID: 122179539

Max Phase: Preclinical

Molecular Formula: C16H18N2O3

Molecular Weight: 286.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N2CCCCC2)ccc1/C=C(\C#N)C(=O)O

Standard InChI:  InChI=1S/C16H18N2O3/c1-21-15-10-14(18-7-3-2-4-8-18)6-5-12(15)9-13(11-17)16(19)20/h5-6,9-10H,2-4,7-8H2,1H3,(H,19,20)/b13-9+

Standard InChI Key:  YEDHRYWTPAZLTH-UKTHLTGXSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    5.1945   -3.0045    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
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    3.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2389    0.8891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -1.9554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    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
   -5.2046    2.6918    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
    3.8991   -0.7525    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
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8978   -0.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    1.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 14  2  2  0
 18 14  1  0
 20 13  1  0
  2 21  1  0
  4  1  1  0
 21 16  1  0
 18  5  1  0
 12 15  1  0
 16  4  1  0
 17 12  2  0
  9 11  1  0
 21 11  1  0
  1  9  1  0
 15 18  2  0
  3  6  2  0
 20  8  2  0
  5  7  1  0
  2 17  1  0
 15  3  1  0
  6 19  1  0
 19 10  3  0
  6 20  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA3582501

   ---

2. Parent:

   

   ALA3582501

   ---

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: 286.33

Molecular Weight (Monoisotopic): 286.1317

AlogP: 2.68

#Rotatable Bonds: 4

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: 2.11

CX Basic pKa: 4.30

CX LogP: 0.84

CX LogD: -0.76

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.68

Np Likeness Score: -0.94

References

1. 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]

2. Murray, Clare M CM and 26 more authors.  2005-12  Monocarboxylate transporter MCT1 is a target for immunosuppression.  [PMID:16370372]

3. Wang, Hui H and 5 more authors.  2014-09-11  Synthesis and structure-activity relationships of pteridine dione and trione monocarboxylate transporter 1 inhibitors.  [PMID:25068893]

4. Nair, Reji N and 9 more authors.  2016-05-01  Exploiting the co-reliance of tumours upon transport of amino acids and lactate: Gln and Tyr conjugates of MCT1 inhibitors.  [PMID:27347360]

Source

Source(1):

• Scientific Literature