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

ID: ALA4779736

PubChem CID: 162662398

Max Phase: Preclinical

Molecular Formula: C21H16N2O5S

Molecular Weight: 408.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N[C@@H]1CCN(C(=O)c2csc3c(O)c4c(c(O)c23)C(=O)c2ccccc2C4=O)C1

Standard InChI:  InChI=1S/C21H16N2O5S/c22-9-5-6-23(7-9)21(28)12-8-29-20-13(12)18(26)14-15(19(20)27)17(25)11-4-2-1-3-10(11)16(14)24/h1-4,8-9,26-27H,5-7,22H2/t9-/m1/s1

Standard InChI Key:  CIYYLIRNMOJGCH-SECBINFHSA-N

Molfile:  

 
     RDKit          2D

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   38.6866   -2.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3952   -2.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3940   -3.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1041   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   42.2379   -3.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0196   -3.7119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.5024   -3.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   40.1065   -1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   41.5305   -4.6880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.2711   -1.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0704   -1.4346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7240   -0.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.6735   -1.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3810   -1.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2107   -0.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3979   -0.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1277   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 26 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4779736

   ---

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: 408.44

Molecular Weight (Monoisotopic): 408.0780

AlogP: 2.26

#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: 9.26

CX LogP: 2.00

CX LogD: 1.99

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -0.33

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