5-Butyl-2-hexylphenanthridin-6(5H)-one

ID: ALA3259997

PubChem CID: 71082496

Max Phase: Preclinical

Molecular Formula: C23H29NO

Molecular Weight: 335.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCc1ccc2c(c1)c1ccccc1c(=O)n2CCCC

Standard InChI:  InChI=1S/C23H29NO/c1-3-5-7-8-11-18-14-15-22-21(17-18)19-12-9-10-13-20(19)23(25)24(22)16-6-4-2/h9-10,12-15,17H,3-8,11,16H2,1-2H3

Standard InChI Key:  FQHADSJCOQHCSU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.3302  -20.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3291  -21.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0371  -22.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0354  -20.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7440  -20.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7428  -21.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1699  -20.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4553  -20.5076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1687  -21.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4523  -22.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4474  -22.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1583  -23.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8755  -22.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8768  -22.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8786  -20.5166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4553  -19.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1630  -19.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1631  -18.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8708  -18.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6211  -22.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9137  -21.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9143  -20.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2069  -20.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2076  -19.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9156  -19.2919    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  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7 15  2  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3259997

   5-butyl-2-hexylphenanthridin-6(5H)-one

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: 335.49

Molecular Weight (Monoisotopic): 335.2249

AlogP: 6.08

#Rotatable Bonds: 8

Polar Surface Area: 22.00

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.66

CX LogD: 6.66

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.36

Np Likeness Score: -0.50

References

1. Nishiyama Y, Nakamura M, Misawa T, Nakagomi M, Makishima M, Ishikawa M, Hashimoto Y..  (2014)  Structure-activity relationship-guided development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists with a phenanthridin-6(5H)-one skeleton from a liver X receptor ligand.,  22  (9): [PMID:24702856] [10.1016/j.bmc.2014.03.007]

Source

Source(1):

• Scientific Literature