2-((bis(2-chloroethyl)amino)(thiophen-2-yl)methyl)-1,4-dihydroxyanthracene-9,10-dione

ID: ALA4440907

PubChem CID: 141750635

Max Phase: Preclinical

Molecular Formula: C23H19Cl2NO4S

Molecular Weight: 476.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2C(=O)c2c(O)c(C(c3ccsc3)N(CCCl)CCCl)cc(O)c21

Standard InChI:  InChI=1S/C23H19Cl2NO4S/c24-6-8-26(9-7-25)20(13-5-10-31-12-13)16-11-17(27)18-19(23(16)30)22(29)15-4-2-1-3-14(15)21(18)28/h1-5,10-12,20,27,30H,6-9H2

Standard InChI Key:  IJBUOJARHXEQRU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.4123   -5.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4123   -4.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7070   -5.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7096   -4.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0058   -4.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2991   -4.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3005   -5.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0048   -5.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1176   -4.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1160   -5.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8202   -5.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5265   -5.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5241   -4.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8193   -4.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4109   -3.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4135   -6.4550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8195   -6.4560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8174   -3.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2305   -4.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2279   -3.1853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9360   -4.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9343   -2.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5189   -2.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5163   -1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8073   -1.5555    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.9317   -1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6381   -1.5464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.0224   -5.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8186   -5.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2240   -4.6759    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.6782   -4.0724    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
 19 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  1  0
 21 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4440907

   ---

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: 476.38

Molecular Weight (Monoisotopic): 475.0412

AlogP: 4.80

#Rotatable Bonds: 7

Polar Surface Area: 77.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.85

CX Basic pKa: 3.82

CX LogP: 6.45

CX LogD: 6.31

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -0.05

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