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

ID: ALA4786975

PubChem CID: 162668030

Max Phase: Preclinical

Molecular Formula: C22H18N2O5S

Molecular Weight: 422.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC1CCCN(C(=O)c2csc3c(O)c4c(c(O)c23)C(=O)c2ccccc2C4=O)C1

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

Standard InChI Key:  SKDUUMQIHAJZOY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   39.7863  -29.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   41.9201  -28.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7018  -29.0035    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.1846  -28.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   39.7887  -26.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   41.2127  -29.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9533  -26.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7526  -26.7263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4062  -26.2895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.2997  -27.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0048  -25.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8040  -25.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0989  -27.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3511  -26.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6460  -27.7701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 16 17  2  0
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  7 19  2  0
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 11 21  1  0
 17 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 23 26  1  0
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 25 28  1  0
 27 29  1  0
 28 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4786975

   ---

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: 9.29

CX LogP: 2.52

CX LogD: 2.51

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -0.28

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