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

ID: ALA4777973

PubChem CID: 162644468

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)N1CCCC(N)C1)C(=O)c1ccccc1C3=O

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

Standard InChI Key:  HRJCCLWXMXAUIU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   26.2271  -27.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2260  -28.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9340  -29.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9322  -27.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6409  -27.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6397  -28.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3498  -29.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3521  -27.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0668  -27.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0655  -28.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7748  -29.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7733  -27.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4832  -27.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4835  -28.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2652  -28.9127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7480  -28.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2646  -27.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3522  -26.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3492  -29.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7710  -26.6140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7761  -29.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5168  -26.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3160  -26.6355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9697  -26.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5652  -28.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5682  -25.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8631  -27.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3675  -25.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6624  -27.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9145  -26.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2095  -27.6793    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
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777973

   ---

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: 7.65

CX Basic pKa: 9.02

CX LogP: 1.94

CX LogD: 1.68

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -0.10

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