1,4-dihydroxy-2-(hydroxy(4-(methylthio)phenyl)methyl)anthracene-9,10-dione

ID: ALA4586039

PubChem CID: 155566929

Max Phase: Preclinical

Molecular Formula: C22H16O5S

Molecular Weight: 392.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CSc1ccc(C(O)c2cc(O)c3c(c2O)C(=O)c2ccccc2C3=O)cc1

Standard InChI:  InChI=1S/C22H16O5S/c1-28-12-8-6-11(7-9-12)19(24)15-10-16(23)17-18(22(15)27)21(26)14-5-3-2-4-13(14)20(17)25/h2-10,19,23-24,27H,1H3

Standard InChI Key:  MTRAKVLZHXDCLK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.3071  -17.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071  -16.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6019  -17.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6044  -16.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007  -16.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939  -16.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1953  -17.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8996  -17.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0124  -16.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0108  -17.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7150  -17.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4213  -17.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190  -16.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7142  -16.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057  -15.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3083  -18.5436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7144  -18.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7122  -15.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1254  -16.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1228  -15.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8309  -16.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8321  -17.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5403  -17.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2477  -17.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2424  -16.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5337  -16.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9572  -17.7155    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -18.5327    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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA4586039

   ---

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: 392.43

Molecular Weight (Monoisotopic): 392.0718

AlogP: 3.68

#Rotatable Bonds: 3

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: 5.26

CX LogD: 5.22

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: 0.49

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