3a-Ethynyl-6-oxo-2,3,3a,6-tetrahydro-1H-indene-5-carbonitrile

ID: ALA3577128

PubChem CID: 122177481

Max Phase: Preclinical

Molecular Formula: C12H9NO

Molecular Weight: 183.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CC12C=C(C#N)C(=O)C=C1CCC2

Standard InChI:  InChI=1S/C12H9NO/c1-2-12-5-3-4-10(12)6-11(14)9(7-12)8-13/h1,6-7H,3-5H2

Standard InChI Key:  WRPUUSQAMFPAII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560   -1.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    1.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6635    2.0821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    2.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939    3.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0
  1  4  1  0
  8  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  6  7  3  0
  3  6  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  8 13  1  0
 13 14  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577128

   ---

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: 183.21

Molecular Weight (Monoisotopic): 183.0684

AlogP: 1.75

#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: 1.74

CX LogD: 1.74

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.54

Np Likeness Score: 0.77

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