alpha-phenyl tropolone

ID: ALA2408237

PubChem CID: 10584105

Max Phase: Preclinical

Molecular Formula: C13H10O2

Molecular Weight: 198.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c(O)ccccc1-c1ccccc1

Standard InChI:  InChI=1S/C13H10O2/c14-12-9-5-4-8-11(13(12)15)10-6-2-1-3-7-10/h1-9H,(H,14,15)

Standard InChI Key:  MUSVYQMQNAIUDU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   13.7072   -1.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7177   -2.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4621   -2.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6530   -3.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1493   -4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322   -4.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8161   -3.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9906   -2.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3421   -2.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1628   -2.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8748   -2.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5780   -2.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5703   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8535   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1534   -1.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  8  1  0
  8  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  3 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2408237

   MO-OH-Phe

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: 198.22

Molecular Weight (Monoisotopic): 198.0681

AlogP: 2.42

#Rotatable Bonds: 1

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.01

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.76

Np Likeness Score: 0.16

References

1. Ononye SN, VanHeyst MD, Oblak EZ, Zhou W, Ammar M, Anderson AC, Wright DL..  (2013)  Tropolones as lead-like natural products: the development of potent and selective histone deacetylase inhibitors.,  4  (8): [PMID:24900743] [10.1021/ml400158k]

2. Ononye SN, Vanheyst MD, Giardina C, Wright DL, Anderson AC..  (2014)  Studies on the antiproliferative effects of tropolone derivatives in Jurkat T-lymphocyte cells.,  22  (7): [PMID:24613456] [10.1016/j.bmc.2014.02.018]

Source

Source(1):

• Scientific Literature