4,11-Dihydroxy-5,10-dioxo-N-(piperidin-4-yl)-5,10-dihydroanthra[2,3-b]thiophene-3-carboxamide

ID: ALA4782219

PubChem CID: 162665021

Max Phase: Preclinical

Molecular Formula: C22H18N2O5S

Molecular Weight: 422.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2C(=O)c2c1c(O)c1scc(C(=O)NC3CCNCC3)c1c2O

Standard InChI:  InChI=1S/C22H18N2O5S/c25-17-11-3-1-2-4-12(11)18(26)16-15(17)19(27)14-13(9-30-21(14)20(16)28)22(29)24-10-5-7-23-8-6-10/h1-4,9-10,23,27-28H,5-8H2,(H,24,29)

Standard InChI Key:  WLTRDPCHZQRHQQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.4480  -19.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4469  -19.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1549  -20.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1531  -18.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8617  -19.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8606  -19.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5707  -20.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5730  -18.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2877  -19.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2864  -19.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9957  -20.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9942  -18.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7041  -19.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7044  -19.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4861  -20.1547    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9689  -19.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4855  -18.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5731  -17.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5701  -21.1344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9919  -17.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9970  -21.1308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7377  -18.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5369  -17.8775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1906  -17.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0840  -18.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8833  -18.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8319  -19.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4304  -18.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1782  -19.6986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3789  -19.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  8 18  2  0
  7 19  2  0
 12 20  1  0
 11 21  1  0
 17 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 26 28  1  0
 27 30  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4782219

   ---

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: 422.46

Molecular Weight (Monoisotopic): 422.0936

AlogP: 2.57

#Rotatable Bonds: 2

Polar Surface Area: 115.73

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.05

CX Basic pKa: 10.04

CX LogP: 2.07

CX LogD: 2.05

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.37

Np Likeness Score: -0.19

References

1. Tikhomirov AS,Litvinova VA,Andreeva DV,Tsvetkov VB,Dezhenkova LG,Volodina YL,Kaluzhny DN,Treshalin ID,Schols D,Ramonova AA,Moisenovich MM,Shtil AA,Shchekotikhin AE.  (2020)  Amides of pyrrole- and thiophene-fused anthraquinone derivatives: A role of the heterocyclic core in antitumor properties.,  199  [PMID:32428792] [10.1016/j.ejmech.2020.112294]

Source

Source(1):

• Scientific Literature