2,7-dihydroxy-4-methyl-5-[3-(1-naphthyl)benzoyl]cyclohepta-2,4,6-trien-1-one

ID: ALA4531945

PubChem CID: 137119475

Max Phase: Preclinical

Molecular Formula: C25H18O4

Molecular Weight: 382.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c(=O)c(O)cc1C(=O)c1cccc(-c2cccc3ccccc23)c1

Standard InChI:  InChI=1S/C25H18O4/c1-15-12-22(26)25(29)23(27)14-21(15)24(28)18-9-4-8-17(13-18)20-11-5-7-16-6-2-3-10-19(16)20/h2-14H,1H3,(H2,26,27,29)

Standard InChI Key:  LYHHBANOTFIMCY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.0559  -12.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7903  -13.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1192  -14.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9711  -14.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6274  -14.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4497  -14.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0654  -12.0660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4374  -12.7456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6775  -12.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2666  -15.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7967  -15.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3294  -16.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6150  -15.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9632  -16.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7808  -16.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2489  -15.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8977  -14.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0812  -14.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3647  -14.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2995  -12.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4764  -12.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0112  -13.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6491  -13.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1839  -14.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5320  -15.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3491  -15.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8169  -14.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4621  -13.6805    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
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  5  7  1  0
  6  7  2  0
  2  8  2  0
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  1 10  1  0
  6 11  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
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 15 16  1  0
 16 17  2  0
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 18 19  2  0
 19 14  1  0
 20 25  2  0
 24 21  2  0
 21 22  1  0
 22 23  2  0
 23 20  1  0
 18 20  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531945

   ---

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: 382.42

Molecular Weight (Monoisotopic): 382.1205

AlogP: 4.82

#Rotatable Bonds: 3

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.58

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 4.91

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -0.11

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