2-((4-ethoxyphenyl)(hydroxy)methyl)-1,4-dihydroxyanthracene-9,10-dione

ID: ALA4464296

PubChem CID: 141750623

Max Phase: Preclinical

Molecular Formula: C23H18O6

Molecular Weight: 390.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1ccc(C(O)c2cc(O)c3c(c2O)C(=O)c2ccccc2C3=O)cc1

Standard InChI:  InChI=1S/C23H18O6/c1-2-29-13-9-7-12(8-10-13)20(25)16-11-17(24)18-19(23(16)28)22(27)15-6-4-3-5-14(15)21(18)26/h3-11,20,24-25,28H,2H2,1H3

Standard InChI Key:  YLLAKPQTCZTGJR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.8881  -14.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1829  -16.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1854  -15.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4817  -14.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7749  -15.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7763  -16.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4806  -16.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5934  -15.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5918  -16.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2960  -16.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0023  -16.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0000  -15.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2952  -14.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8867  -14.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8893  -17.3715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2954  -17.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2932  -14.1091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7064  -14.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7038  -14.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4119  -15.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4131  -16.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1213  -16.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8287  -16.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8234  -15.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1147  -14.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5382  -16.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2441  -16.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9536  -16.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  3  1  1  0
  1 10  1  0
  9  2  1  0
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  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
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  2 15  2  0
  1 16  2  0
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 14 18  1  0
 13 19  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 19 21  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4464296

   ---

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: 390.39

Molecular Weight (Monoisotopic): 390.1103

AlogP: 3.35

#Rotatable Bonds: 4

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: 4.83

CX LogD: 4.79

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: 0.53

References

1. Liu Y, Liang Y, Jiang J, Qin Q, Wang L, Liu X..  (2019)  Design, synthesis and biological evaluation of 1,4-dihydroxyanthraquinone derivatives as anticancer agents.,  29  (9): [PMID:30846253] [10.1016/j.bmcl.2019.02.026]

Source

Source(1):

• Scientific Literature