ID: ALA2172212

Max Phase: Preclinical

Molecular Formula: C19H17N3O2

Molecular Weight: 319.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  NCCCn1c2c(c3ccc(N)cc3c1=O)C(=O)c1ccccc1-2

Standard InChI:  InChI=1S/C19H17N3O2/c20-8-3-9-22-17-13-4-1-2-5-14(13)18(23)16(17)12-7-6-11(21)10-15(12)19(22)24/h1-2,4-7,10H,3,8-9,20-21H2

Standard InChI Key:  AEJWFHDNVYSNLA-UHFFFAOYSA-N

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

Properties

Molecular Weight: 319.36

Molecular Weight (Monoisotopic): 319.1321

AlogP: 2.14

#Rotatable Bonds: 3

Polar Surface Area: 91.11

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.57

CX LogP: 0.55

CX LogD: -1.56

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: 0.23

References

1. Chen L, Conda-Sheridan M, Reddy PV, Morrell A, Park EJ, Kondratyuk TP, Pezzuto JM, van Breemen RB, Cushman M..  (2012)  Identification, synthesis, and biological evaluation of the metabolites of 3-amino-6-(3'-aminopropyl)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)dione (AM6-36), a promising rexinoid lead compound for the development of cancer chemotherapeutic and chemopreventive agents.,  55  (12): [PMID:22712432] [10.1021/jm3006806]

2. Conda-Sheridan M, Reddy PV, Morrell A, Cobb BT, Marchand C, Agama K, Chergui A, Renaud A, Stephen AG, Bindu LK, Pommier Y, Cushman M..  (2013)  Synthesis and biological evaluation of indenoisoquinolines that inhibit both tyrosyl-DNA phosphodiesterase I (Tdp1) and topoisomerase I (Top1).,  56  (1): [PMID:23259865] [10.1021/jm3014458]

3. Conda-Sheridan M, Park EJ, Beck DE, Reddy PV, Nguyen TX, Hu B, Chen L, White JJ, van Breemen RB, Pezzuto JM, Cushman M..  (2013)  Design, synthesis, and biological evaluation of indenoisoquinoline rexinoids with chemopreventive potential.,  56  (6): [PMID:23472886] [10.1021/jm400026k]

4.  (2014)  Synthesis and use of dual tyrosyl-DNA phosphodiesterase I (TDP1)- topoisomerase I (TOP1) inhibitors, 

5.  (2016)  Synthesis and use of dual tyrosyl-DNA phosphodiesterase I (Tdp1)—topoisomerase I (Top1) inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database