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

ID: ALA4533691

PubChem CID: 124132306

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-c1ccc(-c2ccc3ccccc3c2)cc1

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

Standard InChI Key:  ILBIRAPXPVPOMM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.5869   -2.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3245   -1.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0588   -2.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3960   -2.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2355   -2.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9001   -3.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7182   -3.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3340   -0.8441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7018   -1.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9543   -1.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5393   -4.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0652   -4.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5972   -4.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9435   -5.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7586   -5.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2261   -4.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8772   -4.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1069   -6.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6388   -7.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9861   -7.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9180   -6.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2679   -7.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8027   -7.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1537   -8.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9696   -8.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4333   -8.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0797   -7.2708    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
 15 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:

   

   ALA4533691

   ---

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: 10.03

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 5.24

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: 0.16

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