ID: ALA123218

Max Phase: Preclinical

Molecular Formula: C18H13NO3

Molecular Weight: 291.31

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C1c2ccccc2-c2c1c1ccccc1c(=O)n2CCO

Standard InChI:  InChI=1S/C18H13NO3/c20-10-9-19-16-12-6-2-3-7-13(12)17(21)15(16)11-5-1-4-8-14(11)18(19)22/h1-8,20H,9-10H2

Standard InChI Key:  UHXGJXGJNJTBRV-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 291.31

Molecular Weight (Monoisotopic): 291.0895

AlogP: 2.21

#Rotatable Bonds: 2

Polar Surface Area: 59.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.62

Np Likeness Score: 0.17

References

1. Cushman M, Jayaraman M, Vroman JA, Fukunaga AK, Fox BM, Kohlhagen G, Strumberg D, Pommier Y..  (2000)  Synthesis of new indeno[1,2-c]isoquinolines: cytotoxic non-camptothecin topoisomerase I inhibitors.,  43  (20): [PMID:11020283] [10.1021/jm000029d]

2. Nagarajan M, Morrell A, Fort BC, Meckley MR, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2004)  Synthesis and anticancer activity of simplified indenoisoquinoline topoisomerase I inhibitors lacking substituents on the aromatic rings.,  47  (23): [PMID:15509164] [10.1021/jm040025z]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Nguyen TX, Morrell A, Conda-Sheridan M, Marchand C, Agama K, Bermingham A, Stephen AG, Chergui A, Naumova A, Fisher R, O'Keefe BR, Pommier Y, Cushman M..  (2012)  Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase I (Tdp1)-topoisomerase I (Top1) inhibitors.,  55  (9): [PMID:22536944] [10.1021/jm300335n]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays