10a-Ethynyl-3-oxo-3,9,10,10a-tetrahydrophenanthrene-2-carbonitrile

ID: ALA3577131

PubChem CID: 122177484

Max Phase: Preclinical

Molecular Formula: C17H11NO

Molecular Weight: 245.28

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  C#CC12C=C(C#N)C(=O)C=C1c1ccccc1CC2

Standard InChI:  InChI=1S/C17H11NO/c1-2-17-8-7-12-5-3-4-6-14(12)15(17)9-16(19)13(10-17)11-18/h1,3-6,9-10H,7-8H2

Standard InChI Key:  IMCDSEHQYWDCNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  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
  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
M  END

Alternative Forms

  1. Parent:

    ALA3577131

    ---

Associated Targets(non-human)

Nfe2l2 KEAP1/NRF2 (98 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos2 Nitric oxide synthase, inducible (3573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 245.28Molecular Weight (Monoisotopic): 245.0841AlogP: 2.67#Rotatable Bonds:
Polar Surface Area: 40.86Molecular Species: NEUTRALHBA: 2HBD:
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 3.09CX LogD: 3.09
Aromatic Rings: 1Heavy Atoms: 19QED Weighted: 0.66Np Likeness Score: 0.42

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