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

ID: ALA4569853

PubChem CID: 141750627

Max Phase: Preclinical

Molecular Formula: C21H12Cl2O5

Molecular Weight: 415.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2C(=O)c2c(O)c(C(O)c3ccc(Cl)cc3Cl)cc(O)c21

Standard InChI:  InChI=1S/C21H12Cl2O5/c22-9-5-6-12(14(23)7-9)18(25)13-8-15(24)16-17(21(13)28)20(27)11-4-2-1-3-10(11)19(16)26/h1-8,18,24-25,28H

Standard InChI Key:  PWEUEAOVQWBFCM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.8779   -3.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726   -5.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1752   -4.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714   -3.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7647   -4.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7661   -5.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4704   -5.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5832   -4.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816   -5.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2858   -5.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921   -5.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9898   -4.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2850   -3.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8765   -2.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791   -6.2445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2851   -6.2455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830   -2.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6961   -3.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6935   -2.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4016   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4029   -5.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1111   -5.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8185   -5.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8132   -4.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1045   -3.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0996   -2.9699    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.5280   -5.4164    0.0000 Cl  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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 26 21  1  0
 19 21  1  0
 26 27  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4569853

   ---

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: 415.23

Molecular Weight (Monoisotopic): 414.0062

AlogP: 4.26

#Rotatable Bonds: 2

Polar Surface Area: 94.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: 5.84

CX LogD: 5.80

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: 0.46

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