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

ID: ALA3582424

PubChem CID: 71667550

Max Phase: Preclinical

Molecular Formula: C17H18N2O3

Molecular Weight: 298.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H18N2O3/c1-4-8-19(9-5-2)15-7-6-13(16(11-15)22-3)10-14(12-18)17(20)21/h4-7,10-11H,1-2,8-9H2,3H3,(H,20,21)/b14-10+

Standard InChI Key:  YBZMATKXBMEIAT-GXDHUFHOSA-N

Molfile:  

     RDKit          2D

 22 22  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
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471    5.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2938    3.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890    5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    5.8610    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
 16 20  1  0
 20 21  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582424

   (E)-3-[4-[bis(prop-2-enyl)amino]-2-methoxyphenyl]-2-cyanoprop-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: 298.34

Molecular Weight (Monoisotopic): 298.1317

AlogP: 2.87

#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: 2.61

CX Basic pKa: 1.45

CX LogP: 2.90

CX LogD: -0.16

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.45

Np Likeness Score: -0.72

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, 

Source

Source(2):

• Scientific Literature
• BindingDB Database