3-(4-Aminopiperidin-1-carbonyl)-4,11-dihydroxy-2-methyl-1H-naphtho[2,3-f]indole-5,10-dione

ID: ALA4794061

PubChem CID: 162673017

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)N1CCC(N)CC1)C(=O)c1ccccc1C3=O

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

Standard InChI Key:  MQHNWBGDXWFCCN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.6247  -27.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236  -28.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316  -28.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3298  -27.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384  -27.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373  -28.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474  -28.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497  -27.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4644  -27.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4631  -28.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1724  -28.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1709  -27.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8808  -27.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8811  -28.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6628  -28.6032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1456  -27.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6622  -27.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7498  -26.2981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468  -29.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1686  -26.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1737  -29.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9144  -26.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7136  -26.3260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3673  -25.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9628  -27.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9658  -25.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2607  -26.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7651  -25.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0600  -26.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3121  -25.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1114  -25.8151    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
 16 25  1  0
 23 26  1  0
 23 27  1  0
 26 28  1  0
 27 29  1  0
 28 30  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794061

   ---

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: 2.23

#Rotatable Bonds: 1

Polar Surface Area: 136.72

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.66

CX Basic pKa: 10.08

CX LogP: 1.44

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -0.14

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