2-(4-Methoxybenzoyl)-1,4-naphthohydroquinone

ID: ALA3104267

PubChem CID: 76335553

Max Phase: Preclinical

Molecular Formula: C18H14O4

Molecular Weight: 294.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)c2cc(O)c3ccccc3c2O)cc1

Standard InChI:  InChI=1S/C18H14O4/c1-22-12-8-6-11(7-9-12)17(20)15-10-16(19)13-4-2-3-5-14(13)18(15)21/h2-10,19,21H,1H3

Standard InChI Key:  YHLAGMZBXXXSDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   11.3483   -2.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3471   -3.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0619   -4.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0601   -2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7754   -2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7762   -3.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4915   -4.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2065   -3.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2017   -2.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4859   -2.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9136   -2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6306   -2.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6310   -3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3471   -4.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0600   -3.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0523   -2.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3356   -2.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4932   -5.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4815   -1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7774   -4.1451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9086   -1.6891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4889   -3.7274    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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9 11  1  0
 11 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
  7 18  1  0
 10 19  1  0
 15 20  1  0
 11 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3104267

   (1,4-Dihydroxynaphthalen-2-yl)-(4-methoxyphenyl)methanone

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: 294.31

Molecular Weight (Monoisotopic): 294.0892

AlogP: 3.49

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.27

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 3.94

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: 0.11

References

1. Pedroza DA, De Leon F, Varela-Ramirez A, Lema C, Aguilera RJ, Mito S..  (2014)  The cytotoxic effect of 2-acylated-1,4-naphthohydroquinones on leukemia/lymphoma cells.,  22  (2): [PMID:24368029] [10.1016/j.bmc.2013.12.007]

Source

Source(1):

• Scientific Literature