2,7-dihydroxy-4-methyl-5-(3-(naphthalen-2-yl)phenyl)cyclohepta-2,4,6-trien-1-one

ID: ALA4573564

PubChem CID: 124132296

Max Phase: Preclinical

Molecular Formula: C24H18O3

Molecular Weight: 354.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c(=O)c(O)cc1-c1cccc(-c2ccc3ccccc3c2)c1

Standard InChI:  InChI=1S/C24H18O3/c1-15-11-22(25)24(27)23(26)14-21(15)20-8-4-7-18(13-20)19-10-9-16-5-2-3-6-17(16)12-19/h2-14H,1H3,(H2,25,26,27)

Standard InChI Key:  SLQWBULJVNGZBQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   22.4959   -2.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2375   -1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9760   -2.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3008   -3.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1527   -3.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8090   -3.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6313   -3.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2470   -1.1784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6190   -1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8591   -1.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4482   -4.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9824   -4.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5102   -5.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8566   -5.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6758   -6.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1474   -5.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7985   -4.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9631   -5.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3120   -6.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1298   -6.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4291   -4.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2459   -4.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5959   -5.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4155   -5.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8860   -4.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5269   -4.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7084   -4.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  3  5  2  0
  4  6  1  0
  5  7  1  0
  6  7  2  0
  2  8  2  0
  3  9  1  0
  1 10  1  0
  6 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 23  2  0
 22 21  2  0
 21 18  1  0
 16 18  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4573564

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 354.41

Molecular Weight (Monoisotopic): 354.1256

AlogP: 5.25

#Rotatable Bonds: 2

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.12

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 5.24

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: 0.13

References

1. Berkowitz AJ, Franson AD, Gazquez Cassals A, Donald KA, Yu AJ, Garimallaprabhakaran AK, Morrison LA, Murelli RP..  (2019)  Importance of lipophilicity for potent anti-herpes simplex virus-1 activity of α-hydroxytropolones.,  10  (7): [PMID:31391890] [10.1039/C9MD00225A]

Source

Source(1):

• Scientific Literature