3-(4-Aminopiperidine-1-carbonyl)-4,11-dihydroxyanthra[2,3-b]thiophene-5,10-dione

ID: ALA4780528

PubChem CID: 162663487

Max Phase: Preclinical

Molecular Formula: C22H18N2O5S

Molecular Weight: 422.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC1CCN(C(=O)c2csc3c(O)c4c(c(O)c23)C(=O)c2ccccc2C4=O)CC1

Standard InChI:  InChI=1S/C22H18N2O5S/c23-10-5-7-24(8-6-10)22(29)13-9-30-21-14(13)19(27)15-16(20(21)28)18(26)12-4-2-1-3-11(12)17(15)25/h1-4,9-10,27-28H,5-8,23H2

Standard InChI Key:  YDXMACOABPLVLZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.3531  -27.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3519  -28.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0600  -28.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0582  -27.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7668  -27.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7656  -28.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4757  -28.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4781  -27.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1927  -27.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1915  -28.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9008  -28.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8993  -27.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6091  -27.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6095  -28.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3912  -28.5990    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.8740  -27.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3906  -27.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4781  -26.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4752  -29.5787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8969  -26.3003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9021  -29.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6428  -26.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4420  -26.3218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0957  -25.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9891  -26.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6942  -25.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4934  -25.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7883  -26.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0405  -25.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8398  -25.8110    0.0000 N   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
 23 26  1  0
 26 27  1  0
 25 28  1  0
 27 29  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4780528

   ---

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: 2.65

#Rotatable Bonds: 1

Polar Surface Area: 120.93

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.04

CX Basic pKa: 9.99

CX LogP: 2.07

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -0.32

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