ID: ALA127691

Max Phase: Preclinical

Molecular Formula: C18H16N2O3

Molecular Weight: 308.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  Oc1ncc(Cc2cccc(OCc3ccccc3)c2)c(O)n1

Standard InChI:  InChI=1S/C18H16N2O3/c21-17-15(11-19-18(22)20-17)9-14-7-4-8-16(10-14)23-12-13-5-2-1-3-6-13/h1-8,10-11H,9,12H2,(H2,19,20,21,22)

Standard InChI Key:  ZJQDPXONNQFKKC-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: 308.34

Molecular Weight (Monoisotopic): 308.1161

AlogP: 3.06

#Rotatable Bonds: 5

Polar Surface Area: 75.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.20

CX Basic pKa:

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -0.45

References

1. Orr GF, Musso DL, Boswell GE, Kelley JL, Joyner SS, Davis ST, Baccanari DP..  (1995)  Inhibition of uridine phosphorylase: synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils.,  38  (19): [PMID:7562916] [10.1021/jm00019a015]

2. Kelley JL, Baker BR..  (1982)  Irreversible enzyme inhibitors. 202. Candidate active-site-directed irreversible inhibitors of 5-fluoro-2'-deoxyuridine phosphorylase from Walker 256 rat tumor derived from 1-benzyl-5-(3-ethoxybenzyl)uracil.,  25  (5): [PMID:6211547] [10.1021/jm00347a022]

3. Hattori K, Kohchi Y, Oikawa N, Suda H, Ura M, Ishikawa T, Miwa M, Endoh M, Eda H, Tanimura H, Kawashima A, Horii I, Ishitsuka H, Shimma N..  (2003)  Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine.,  13  (5): [PMID:12617910] [10.1016/s0960-894x(02)01082-x]

Source

Source(1):

• Scientific Literature