ID: ALA2177791

Max Phase: Preclinical

Molecular Formula: C26H28N2O7

Molecular Weight: 480.52

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc2c(cc1O)C(=O)c1c-2n(CCCN2CCOCC2)c(=O)c2cc(OC)c(OC)cc12

Standard InChI:  InChI=1S/C26H28N2O7/c1-32-20-13-16-17(11-19(20)29)25(30)23-15-12-21(33-2)22(34-3)14-18(15)26(31)28(24(16)23)6-4-5-27-7-9-35-10-8-27/h11-14,29H,4-10H2,1-3H3

Standard InChI Key:  DIZYBTAYMOFSCR-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: 480.52

Molecular Weight (Monoisotopic): 480.1897

AlogP: 2.67

#Rotatable Bonds: 7

Polar Surface Area: 99.46

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.31

CX Basic pKa: 6.10

CX LogP: 1.20

CX LogD: 1.13

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.43

Np Likeness Score: 0.05

References

1. Cinelli MA, Reddy PV, Lv PC, Liang JH, Chen L, Agama K, Pommier Y, van Breemen RB, Cushman M..  (2012)  Identification, synthesis, and biological evaluation of metabolites of the experimental cancer treatment drugs indotecan (LMP400) and indimitecan (LMP776) and investigation of isomerically hydroxylated indenoisoquinoline analogues as topoisomerase I poisons.,  55  (24): [PMID:23215354] [10.1021/jm300519w]

2. Roy J, Nguyen TX, Kanduluru AK, Venkatesh C, Lv W, Reddy PV, Low PS, Cushman M..  (2015)  DUPA conjugation of a cytotoxic indenoisoquinoline topoisomerase I inhibitor for selective prostate cancer cell targeting.,  58  (7): [PMID:25822623] [10.1021/jm5018384]

3. Nguyen TX, Abdelmalak M, Marchand C, Agama K, Pommier Y, Cushman M..  (2015)  Synthesis and biological evaluation of nitrated 7-, 8-, 9-, and 10-hydroxyindenoisoquinolines as potential dual topoisomerase I (Top1)-tyrosyl-DNA phosphodiesterase I (TDP1) inhibitors.,  58  (7): [PMID:25811317] [10.1021/acs.jmedchem.5b00136]

Source

Source(1):

• Scientific Literature