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

ID: ALA4796428

PubChem CID: 162674664

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)NC1CCNCC1)C(=O)c1ccccc1C3=O

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

Standard InChI Key:  NJUUUMMZKSXZOE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    1.5917  -19.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5905  -20.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986  -21.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2968  -19.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054  -19.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042  -20.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7143  -21.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167  -19.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4314  -19.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301  -20.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1394  -21.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1379  -19.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8477  -19.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8481  -20.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6298  -21.0256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1126  -20.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292  -19.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167  -18.7205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138  -22.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355  -18.7269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407  -22.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8814  -18.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6806  -18.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3343  -18.3116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9298  -20.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9328  -17.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7320  -17.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3857  -17.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6379  -16.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4371  -16.4164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9842  -17.0235    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
 16 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 27 31  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4796428

   ---

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: 7.67

CX Basic pKa: 10.12

CX LogP: 1.45

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: 0.02

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