2-((3-bromo-4-methoxyphenyl)(hydroxy)methyl)-1,4-dihydroxyanthracene-9,10-dione

ID: ALA4441505

PubChem CID: 155514999

Max Phase: Preclinical

Molecular Formula: C22H15BrO6

Molecular Weight: 455.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C(O)c2cc(O)c3c(c2O)C(=O)c2ccccc2C3=O)cc1Br

Standard InChI:  InChI=1S/C22H15BrO6/c1-29-16-7-6-10(8-14(16)23)19(25)13-9-15(24)17-18(22(13)28)21(27)12-5-3-2-4-11(12)20(17)26/h2-9,19,24-25,28H,1H3

Standard InChI Key:  DTIXQECVDIZHOZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   17.0202  -22.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0202  -21.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3149  -22.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3175  -21.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6137  -21.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9070  -21.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9084  -22.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6127  -22.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7255  -21.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7239  -22.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4281  -22.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1344  -22.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1321  -21.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4273  -21.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0188  -20.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0214  -23.7976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4275  -23.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4253  -20.5352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8385  -21.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8358  -20.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5439  -21.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5452  -22.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2534  -22.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9608  -22.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9555  -21.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2468  -21.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6703  -22.9695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6740  -23.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6604  -21.3293    0.0000 Br  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
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  2 15  2  0
  1 16  2  0
 11 17  1  0
 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
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4441505

   ---

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: 455.26

Molecular Weight (Monoisotopic): 454.0052

AlogP: 3.73

#Rotatable Bonds: 3

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: 5.24

CX LogD: 5.21

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: 0.73

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