3,3-Diethynyl-6-oxocyclohexa-1,4-dienecarbonitrile

ID: ALA3577125

PubChem CID: 122177479

Max Phase: Preclinical

Molecular Formula: C11H5NO

Molecular Weight: 167.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CC1(C#C)C=CC(=O)C(C#N)=C1

Standard InChI:  InChI=1S/C11H5NO/c1-3-11(4-2)6-5-10(13)9(7-11)8-12/h1-2,5-7H

Standard InChI Key:  OSAKXIAFCPXTGN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
    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
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6380   -2.1004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    2.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2993    2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523    2.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522    2.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  8  9  3  0
  5  8  1  0
  3 10  1  0
  3 11  1  0
 11 12  3  0
 10 13  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577125

   ---

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: 167.17

Molecular Weight (Monoisotopic): 167.0371

AlogP: 0.83

#Rotatable Bonds: ┄

Polar Surface Area: 40.86

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.16

CX LogD: 1.16

Aromatic Rings: ┄

Heavy Atoms: 13

QED Weighted: 0.50

Np Likeness Score: 0.51

References

1. Li W, Zheng S, Higgins M, Morra RP, Mendis AT, Chien CW, Ojima I, Mierke DF, Dinkova-Kostova AT, Honda T..  (2015)  New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase.,  58  (11): [PMID:25965897] [10.1021/acs.jmedchem.5b00393]

2. Bensasson RV, Dinkova-Kostova AT, Zheng S, Saito A, Li W, Zoete V, Honda T..  (2016)  Electron affinity of tricyclic, bicyclic, and monocyclic compounds containing cyanoenones correlates with their potency as inducers of a cytoprotective enzyme.,  26  (17): [PMID:27460172] [10.1016/j.bmcl.2016.07.028]

Source

Source(1):

• Scientific Literature