US9296728, 17

ID: ALA3916791

PubChem CID: 71667551

Max Phase: Preclinical

Molecular Formula: C17H14N2O3

Molecular Weight: 294.31

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/C17H14N2O3/c1-4-8-19(9-5-2)15-7-6-13(16(11-15)22-3)10-14(12-18)17(20)21/h1-2,6-7,10-11H,8-9H2,3H3,(H,20,21)/b14-10+

Standard InChI Key:  AUELJRMSNKLDTD-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
   -1.3095    6.4502    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
    1.2852    6.4570    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  3  0
 16 20  1  0
 20 21  1  0
 21 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3916791

   (E)-3-[4-[bis(prop-2-ynyl)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: 294.31

Molecular Weight (Monoisotopic): 294.1004

AlogP: 1.76

#Rotatable Bonds: 6

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: 2.26

CX Basic pKa: ┄

CX LogP: 2.35

CX LogD: -1.16

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.49

Np Likeness Score: -0.78

References

1.  (2016)  Therapeutic compounds, 

Source

Source(1):

• BindingDB Database