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

ID: ALA4465360

PubChem CID: 141750636

Max Phase: Preclinical

Molecular Formula: C19H11BrO5S

Molecular Weight: 431.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2C(=O)c2c(O)c(C(O)c3cc(Br)cs3)cc(O)c21

Standard InChI:  InChI=1S/C19H11BrO5S/c20-8-5-13(26-7-8)16(22)11-6-12(21)14-15(19(11)25)18(24)10-4-2-1-3-9(10)17(14)23/h1-7,16,21-22,25H

Standard InChI Key:  OJZSNCLHSOIOFN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   36.5007   -9.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5007   -8.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7955   -9.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7980   -8.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0943   -8.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3875   -8.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3889   -9.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0932   -9.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2060   -8.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2044   -9.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9086   -9.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6149   -9.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6126   -8.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9078   -8.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4993   -7.4538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5019  -10.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9080  -10.7235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9058   -7.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3190   -8.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3164   -7.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0244   -8.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1108   -9.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9070   -9.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3124   -8.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7667   -8.3400    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.2410  -10.3948    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
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4465360

   ---

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: 431.26

Molecular Weight (Monoisotopic): 429.9511

AlogP: 3.78

#Rotatable Bonds: 2

Polar Surface Area: 94.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: 5.31

CX LogD: 5.28

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: 0.45

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