5-Bromo-10a-ethynyl-3-oxo-3,9,10,10a-tetrahydrophenanthrene-2-carbonitrile

ID: ALA3577133

PubChem CID: 122177486

Max Phase: Preclinical

Molecular Formula: C17H10BrNO

Molecular Weight: 324.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CC12C=C(C#N)C(=O)C=C1c1c(Br)cccc1CC2

Standard InChI:  InChI=1S/C17H10BrNO/c1-2-17-7-6-11-4-3-5-14(18)16(11)13(17)8-15(20)12(9-17)10-19/h1,3-5,8-9H,6-7H2

Standard InChI Key:  XZRSIZIJARFCKL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -3.4277    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466    4.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3678    2.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4111    3.5225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0867   -1.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    1.8928    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 14  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 16 17  3  0
 12 16  1  0
 10 18  1  0
 18 19  3  0
  4 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577133

   ---

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: 324.18

Molecular Weight (Monoisotopic): 322.9946

AlogP: 3.43

#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: 3.85

CX LogD: 3.85

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.69

Np Likeness Score: 0.45

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]

Source

Source(1):

• Scientific Literature