N-(4-chlorobenzyl)-4,9-dioxo-3-(2-(piperidin-1-yl)acetamido)-2,3,4,9-tetrahydronaphtho[2,3-b]thiophene-3-carboxamide hydrochloride

ID: ALA3622411

PubChem CID: 122191808

Max Phase: Preclinical

Molecular Formula: C27H27Cl2N3O4S

Molecular Weight: 524.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(CN1CCCCC1)NC1(C(=O)NCc2ccc(Cl)cc2)CSC2=C1C(=O)c1ccccc1C2=O

Standard InChI:  InChI=1S/C27H26ClN3O4S.ClH/c28-18-10-8-17(9-11-18)14-29-26(35)27(30-21(32)15-31-12-4-1-5-13-31)16-36-25-22(27)23(33)19-6-2-3-7-20(19)24(25)34;/h2-3,6-11H,1,4-5,12-16H2,(H,29,35)(H,30,32);1H

Standard InChI Key:  JEUNFIVMHNCMAB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    8.3805    3.0505    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6043   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    1.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168    1.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7217   -2.6214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7217    2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    1.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8792    0.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045   -1.1298    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    2.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4150    3.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3786    4.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5809    4.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4653    1.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9332    3.0092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2659    0.6893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4020    3.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8700    4.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3375    5.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8023    6.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7996    7.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3321    7.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8673    5.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1714    8.7372    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995    6.3584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    7.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1889    8.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6468    9.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6812    8.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2575    6.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6  9  1  0
  7  8  1  0
  8 13  1  0
 12  9  1  0
  9 10  2  0
  8 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 14 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 19 32  1  0
 32 33  1  0
 32 37  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 524.04

Molecular Weight (Monoisotopic): 523.1333

AlogP: 3.38

#Rotatable Bonds: 6

Polar Surface Area: 95.58

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.43

CX Basic pKa: 5.41

CX LogP: 2.52

CX LogD: 2.52

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.60

Np Likeness Score: -0.90

References

1. Bertamino A, Musella S, Di Sarno V, Ostacolo C, Manfra M, Vanacore D, Stiuso P, Novellino E, Campiglia P, Gomez-Monterrey IM..  (2015)  Dihydrithieno[2,3-b]naphto-4,9-dione analogues as anticancer agents: Synthesis and in cell pharmacological studies.,  102  [PMID:26253231] [10.1016/j.ejmech.2015.07.044]

Source

Source(1):

• Scientific Literature