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

ID: ALA3582422

Cas Number: 1448313-95-8

PubChem CID: 71623055

Max Phase: Preclinical

Molecular Formula: C23H18N2O3

Molecular Weight: 370.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N(c2ccccc2)c2ccccc2)ccc1/C=C(\C#N)C(=O)O

Standard InChI:  InChI=1S/C23H18N2O3/c1-28-22-15-21(13-12-17(22)14-18(16-24)23(26)27)25(19-8-4-2-5-9-19)20-10-6-3-7-11-20/h2-15H,1H3,(H,26,27)/b18-14+

Standard InChI Key:  OOKBWQIMMUTDEE-NBVRZTHBSA-N

Molfile:  

     RDKit          2D

 28 30  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
   -0.0031    3.0008    0.0000 N   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
   -1.3092    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    5.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9021    3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2953    3.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    5.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936    6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8929    5.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935    3.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    3.0040    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  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 16 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582422

   2-Cyano-3-[4-(diphenylamino)-2-methoxyphenyl]prop-2-enoic acid

2. Alternative Forms:

   

   ALA3582422

   ---

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: 370.41

Molecular Weight (Monoisotopic): 370.1317

AlogP: 5.16

#Rotatable Bonds: 6

Polar Surface Area: 73.56

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.03

CX Basic pKa: ┄

CX LogP: 5.11

CX LogD: 1.59

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -0.58

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