N-[2-(2-Dimethylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-8-yl]-acetamide

Names and Identifiers

Canonical SMILES: CC(=O)Nc1cccc2c3c4c(cccc4cc12)C(=O)N(CCN(C)C)C3=O

Standard InChI: InChI=1S/C22H21N3O3/c1-13(26)23-18-9-5-7-15-17(18)12-14-6-4-8-16-19(14)20(15)22(28)25(21(16)27)11-10-24(2)3/h4-9,12H,10-11H2,1-3H3,(H,23,26)

Standard InChI Key: WKTJDJRPGUQVBC-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.0625   -4.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -7.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -7.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -8.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -4.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -8.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -4.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -8.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -2.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -7.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -9.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  6  1  0
  6  3  1  0
  7  4  1  0
  8  7  1  0
  9  5  1  0
 10  9  2  0
 11  8  2  0
 12  1  1  0
 13 11  1  0
 14  2  2  0
 15 13  1  0
 16  3  2  0
 17 15  2  0
 18 12  1  0
 19 18  1  0
 20  6  2  0
 21  7  2  0
 22 24  2  0
 23 25  2  0
 24 20  1  0
 25 21  1  0
 26 15  1  0
 27 19  1  0
 28 19  1  0
  5  4  2  0
  9 22  1  0
 10  8  1  0
 11 23  1  0
M  END

Alternative Forms

Parent:

ALA149619
N-[15-[2-(dimethylamino)ethyl]-14,16-dioxo-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,8,10,12-heptaen-6-yl]acetamide

Associated Targets(Human)

Melanoma cell (242 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ovarian carcinoma cell (138 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

L1210 (27553 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 375.43	Molecular Weight (Monoisotopic): 375.1583	AlogP: 3.11	#Rotatable Bonds: 4
Polar Surface Area: 69.72	Molecular Species: BASE	HBA: 4	HBD: 1
#RO5 Violations: ┄	HBA (Lipinski): 6	HBD (Lipinski): 1	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 13.58	CX Basic pKa: 8.52	CX LogP: 2.15	CX LogD: 1.00
Aromatic Rings: 3	Heavy Atoms: 28	QED Weighted: 0.56	Np Likeness Score: -0.85

References

1. Sami SM, Dorr RT, Alberts DS, Sólyom AM, Remers WA.. (1996) 2-[2'-(Dimethylamino)ethyl]-1,2-dihydro- 3H-dibenz[de,h]isoquinoline-1,3-diones with substituents at positions 4, 8, 9, 10, and 11. Synthesis, antitumor activity, and quantitative structure-activity relationships., 39 (25): [PMID:8960558] [10.1021/jm960623g]
2. Sharma MC, Sharma S, Sharma P, Kumar A. (2013) Comparative QSAR and pharmacophore modeling of substituted 2-[2-(dimethylamino) ethyl]-1, 2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-diones derivatives as anti-tumor activity, 22 (12): [10.1007/s00044-013-0554-z]

Source

Source(1):

Scientific Literature