ID: ALA101299

Max Phase: Preclinical

Molecular Formula: C20H16FN3O4

Molecular Weight: 381.36

Molecule Type: Small molecule

Representations

Synonyms (1): A-62176
Synonyms from Alternative Forms(1):

Canonical SMILES:  N[C@H]1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn4c3c2Oc2ccccc2-4)C1

Standard InChI:  InChI=1S/C20H16FN3O4/c21-13-7-11-16-19(17(13)23-6-5-10(22)8-23)28-15-4-2-1-3-14(15)24(16)9-12(18(11)25)20(26)27/h1-4,7,9-10H,5-6,8,22H2,(H,26,27)/t10-/m0/s1

Standard InChI Key:  OLNJLTFSGFZCKE-JTQLQIEISA-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: 381.36

Molecular Weight (Monoisotopic): 381.1125

AlogP: 2.47

#Rotatable Bonds: 2

Polar Surface Area: 97.79

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 5.24

CX Basic pKa: 9.63

CX LogP: -0.26

CX LogD: -0.26

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -0.36

References

1. Kim MY, Na Y, Vankayalapati H, Gleason-Guzman M, Hurley LH..  (2003)  Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.,  46  (14): [PMID:12825936] [10.1021/jm030096i]

2. Zeng Q, Kwok Y, Kerwin SM, Mangold G, Hurley LH..  (1998)  Design of new topoisomerase II inhibitors based upon a quinobenzoxazine self-assembly model.,  41  (22): [PMID:9784102] [10.1021/jm980265c]

3. Kim MY, Duan W, Gleason-Guzman M, Hurley LH..  (2003)  Design, synthesis, and biological evaluation of a series of fluoroquinoanthroxazines with contrasting dual mechanisms of action against topoisomerase II and G-quadruplexes.,  46  (4): [PMID:12570378] [10.1021/jm0203377]

4. Xu H, Hurley LH..  (2022)  A first-in-class clinical G-quadruplex-targeting drug. The bench-to-bedside translation of the fluoroquinolone QQ58 to CX-5461 (Pidnarulex).,  77  [PMID:36195286] [10.1016/j.bmcl.2022.129016]

Source

Source(1):

• Scientific Literature