4,11-Dihydroxy-2-methyl-5,10-dioxo-N-(piperidin-3-yl)-5,10-dihydro-1H-naphtho[2,3-f]indole-3-carboxamide

ID: ALA4787760

PubChem CID: 162669637

Max Phase: Preclinical

Molecular Formula: C23H21N3O5

Molecular Weight: 419.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2c(O)c3c(c(O)c2c1C(=O)NC1CCCNC1)C(=O)c1ccccc1C3=O

Standard InChI:  InChI=1S/C23H21N3O5/c1-10-14(23(31)26-11-5-4-8-24-9-11)15-18(25-10)22(30)17-16(21(15)29)19(27)12-6-2-3-7-13(12)20(17)28/h2-3,6-7,11,24-25,29-30H,4-5,8-9H2,1H3,(H,26,31)

Standard InChI Key:  OELDTGZISVPQCN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   26.3415  -20.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0496  -21.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0478  -19.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7564  -20.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7552  -20.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4653  -21.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4677  -19.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1823  -20.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.8888  -19.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5987  -20.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5991  -20.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3808  -21.2031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8636  -20.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3802  -19.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4677  -18.8979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4648  -22.1827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8865  -18.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8917  -22.1791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6323  -19.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4316  -18.9258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0853  -18.4891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6808  -20.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6838  -18.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4830  -17.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1367  -17.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3888  -16.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7352  -17.2009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1881  -16.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  7 10  1  0
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  9 10  2  0
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  8 18  2  0
  7 19  2  0
 12 20  1  0
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 17 22  1  0
 22 23  1  0
 22 24  2  0
 16 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4787760

   ---

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: 419.44

Molecular Weight (Monoisotopic): 419.1481

AlogP: 2.14

#Rotatable Bonds: 2

Polar Surface Area: 131.52

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.66

CX Basic pKa: 9.73

CX LogP: 1.95

CX LogD: 1.68

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: 0.03

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