5-(2-(dimethylamino)ethyl)-11,12-dihydro-4H-benzo[c]pyrimido[5,6,1-jk]carbazole-4,6,10(5H,7H)-trione hydrochloride

ID: ALA604052

PubChem CID: 21849939

Max Phase: Preclinical

Molecular Formula: C22H22ClN3O3

Molecular Weight: 375.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ER-37328 | ER-37328|CHEMBL604052|SCHEMBL6623792|18-[2-(Dimethylamino)ethyl]-12,14-diazapentacyclo[10.7.1.02,11.03,8.016,20]icosa-1(20),2(11),3(8),5,13,15-hexaene-7,17,19-trione;hydrochloride

Canonical SMILES:  CN(C)CCC1C(=O)c2cncn3c4c(c(c23)C1=O)C1=C(CC4)C(=O)C=CC1.Cl

Standard InChI:  InChI=1S/C22H21N3O3.ClH/c1-24(2)9-8-14-21(27)15-10-23-11-25-16-7-6-12-13(4-3-5-17(12)26)18(16)19(20(15)25)22(14)28;/h3,5,10-11,14H,4,6-9H2,1-2H3;1H

Standard InChI Key:  WTKWSQVGFMBOGJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    9.3693   -3.3235    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7877   -5.8019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -6.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4116   -6.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0009   -7.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4116   -7.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -7.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6477   -7.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4620   -6.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1788   -7.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9016   -6.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9016   -6.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898   -5.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5429   -6.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7033   -4.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699   -4.5007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209   -4.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6477   -8.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -9.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4116   -9.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0009   -8.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6196   -5.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1788   -8.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754   -8.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6008   -7.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3240   -6.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0314   -7.3343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7509   -6.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0314   -8.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 14  2  0
  2 14  1  0
 15 16  2  0
 16 17  1  0
 13 17  2  0
  2 15  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  6 21  1  0
  7 18  1  0
 12 22  2  0
 10 23  2  0
 21 24  2  0
 25 26  1  0
 27 28  1  0
 27 29  1  0
 26 27  1  0
 11 25  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: 375.43

Molecular Weight (Monoisotopic): 375.1583

AlogP: 2.51

#Rotatable Bonds: 3

Polar Surface Area: 71.75

Molecular Species: ACID

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.84

CX Basic pKa: 7.46

CX LogP: -2.31

CX LogD: -2.39

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: 0.44

References

1. Farghaly TA, Abdalla MM..  (2009)  Synthesis, tautomerism, and antimicrobial, anti-HCV, anti-SSPE, antioxidant, and antitumor activities of arylazobenzosuberones.,  17  (23): [PMID:19864149] [10.1016/j.bmc.2009.10.012]

2. Riyadh SM, Farghaly TA, Abdallah MA, Abdalla MM, Abd El-Aziz MR..  (2010)  New pyrazoles incorporating pyrazolylpyrazole moiety: synthesis, anti-HCV and antitumor activity.,  45  (3): [PMID:20022411] [10.1016/j.ejmech.2009.11.050]

Source

Source(1):

• Scientific Literature