4-(4-chlorobenzylamino)-9,10-dioxo-9,10-dihydroanthracen-1-yl 4-methylbenzenesulfonate

ID: ALA2442837

PubChem CID: 72546225

Max Phase: Preclinical

Molecular Formula: C28H20ClNO5S

Molecular Weight: 517.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)Oc2ccc(NCc3ccc(Cl)cc3)c3c2C(=O)c2ccccc2C3=O)cc1

Standard InChI:  InChI=1S/C28H20ClNO5S/c1-17-6-12-20(13-7-17)36(33,34)35-24-15-14-23(30-16-18-8-10-19(29)11-9-18)25-26(24)28(32)22-5-3-2-4-21(22)27(25)31/h2-15,30H,16H2,1H3

Standard InChI Key:  OXVYDTTZLHYWNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.5925   -1.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7688   -1.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -3.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973   -4.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196   -4.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -3.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3354   -4.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -4.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7721   -4.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4924   -4.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103   -4.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4762   -2.2928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027   -2.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041   -3.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6198   -3.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3308   -3.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3218   -2.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6055   -1.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0479   -3.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -5.6012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2115   -6.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2152   -6.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5033   -7.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -8.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -8.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9362   -8.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9293   -7.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273   -9.3003    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
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 10 18  2  0
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 20  1  1  0
  1 21  1  0
 21 22  2  0
 22 23  1  0
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 24 25  1  0
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 28 29  1  0
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 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2442837

   [4-[(4-Chlorophenyl)methylamino]-9,10-dioxoanthracen-1-yl] 4-methylbenzenesulfonate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 517.99

Molecular Weight (Monoisotopic): 517.0751

AlogP: 5.80

#Rotatable Bonds: 6

Polar Surface Area: 89.54

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 1.24

CX LogP: 7.10

CX LogD: 7.10

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.66

References

1. Sangthong S, Ha H, Teerawattananon T, Ngamrojanavanich N, Neamati N, Muangsin N..  (2013)  Overcoming doxorubicin-resistance in the NCI/ADR-RES model cancer cell line by novel anthracene-9,10-dione derivatives.,  23  (22): [PMID:24095089] [10.1016/j.bmcl.2013.09.004]

Source

Source(1):

• Scientific Literature