ID: ALA213072

Max Phase: Preclinical

Molecular Formula: C19H16N2O2

Molecular Weight: 304.35

Molecule Type: Small molecule

Representations

Canonical SMILES:  NCCCn1c2c(c3ccccc3c1=O)C(=O)c1ccccc1-2

Standard InChI:  InChI=1S/C19H16N2O2/c20-10-5-11-21-17-13-7-2-3-8-14(13)18(22)16(17)12-6-1-4-9-15(12)19(21)23/h1-4,6-9H,5,10-11,20H2

Standard InChI Key:  JWMIPWLLAVVHDH-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: 304.35

Molecular Weight (Monoisotopic): 304.1212

AlogP: 2.56

#Rotatable Bonds: 3

Polar Surface Area: 65.09

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.57

CX LogP: 1.38

CX LogD: -0.73

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: 0.13

References

1. Nagarajan M, Morrell A, Antony S, Kohlhagen G, Agama K, Pommier Y, Ragazzon PA, Garbett NC, Chaires JB, Hollingshead M, Cushman M..  (2006)  Synthesis and biological evaluation of bisindenoisoquinolines as topoisomerase I inhibitors.,  49  (17): [PMID:16913702] [10.1021/jm060046o]

2. Morrell A, Placzek M, Parmley S, Antony S, Dexheimer TS, Pommier Y, Cushman M..  (2007)  Nitrated indenoisoquinolines as topoisomerase I inhibitors: a systematic study and optimization.,  50  (18): [PMID:17696418] [10.1021/jm070361q]

3. Bakshi RP, Sang D, Morrell A, Cushman M, Shapiro TA..  (2009)  Activity of indenoisoquinolines against African trypanosomes.,  53  (1): [PMID:18824603] [10.1128/aac.00650-07]

4. 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]

5. 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]

Source

Source(1):

• Scientific Literature