ID: ALA338604

Max Phase: Phase

Molecular Formula: C20H22N4O2

Molecular Weight: 350.42

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-645809
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCN(CC)CCNc1ccc2ncn3c4ccc(O)cc4c(=O)c1c23

Standard InChI:  InChI=1S/C20H22N4O2/c1-3-23(4-2)10-9-21-15-6-7-16-19-18(15)20(26)14-11-13(25)5-8-17(14)24(19)12-22-16/h5-8,11-12,21,25H,3-4,9-10H2,1-2H3

Standard InChI Key:  CUNDRHORZHFPLY-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 350.42

Molecular Weight (Monoisotopic): 350.1743

AlogP: 2.90

#Rotatable Bonds: 6

Polar Surface Area: 69.87

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.64

CX Basic pKa: 8.62

CX LogP: 2.92

CX LogD: 1.89

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: -0.65

References

1. Cholody WM, Martelli S, Konopa J..  (1992)  Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias.,  35  (2): [PMID:1732555] [10.1021/jm00080a026]

2. Nolan KA, Humphries MP, Bryce RA, Stratford IJ..  (2010)  Imidazoacridin-6-ones as novel inhibitors of the quinone oxidoreductase NQO2.,  20  (9): [PMID:20356739] [10.1016/j.bmcl.2010.03.051]

3. Dunstan MS, Barnes J, Humphries M, Whitehead RC, Bryce RA, Leys D, Stratford IJ, Nolan KA..  (2011)  Novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2): crystal structures, biochemical activity, and intracellular effects of imidazoacridin-6-ones.,  54  (19): [PMID:21859103] [10.1021/jm200416e]

4. Koba M, Baczek T.  (2012)  Importance of some classes of molecular descriptors on classification of antitumor acridinones using factor analysis,  21  (10): [10.1007/s00044-011-9816-9]

5. Koba M, Bączek T..  (2011)  Physicochemical interaction of antitumor acridinone derivatives with DNA in view of QSAR studies.,  20  (8): [PMID:22003274] [10.1007/s00044-010-9487-y]

6. Fedejko-Kap B, Bratton SM, Finel M, Radominska-Pandya A, Mazerska Z..  (2012)  Role of human UDP-glucuronosyltransferases in the biotransformation of the triazoloacridinone and imidazoacridinone antitumor agents C-1305 and C-1311: highly selective substrates for UGT1A10.,  40  (9): [PMID:22659092] [10.1124/dmd.112.045401]

7. Chen JN,Wu XK,Lu CH,Li X.  (2021)  Structure-activity relationship of novel acridone derivatives as antiproliferative agents.,  29  [PMID:33191085] [10.1016/j.bmc.2020.115868]

Source

Source(1):

• Scientific Literature