5'-Methyl-5'-[5-(m,m,p-trimethoxybenzoyloxymethyl)-uracil-1-ylmethyl]-2'-oxo-3'-methylenetetrahydrofuran

ID: ALA3276959

PubChem CID: 12381711

Max Phase: Preclinical

Molecular Formula: C22H24N2O9

Molecular Weight: 460.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC(C)(Cn2cc(COC(=O)c3cc(OC)c(OC)c(OC)c3)c(=O)[nH]c2=O)OC1=O

Standard InChI:  InChI=1S/C22H24N2O9/c1-12-8-22(2,33-19(12)26)11-24-9-14(18(25)23-21(24)28)10-32-20(27)13-6-15(29-3)17(31-5)16(7-13)30-4/h6-7,9H,1,8,10-11H2,2-5H3,(H,23,25,28)

Standard InChI Key:  MZVDXORGVAWLMU-UHFFFAOYSA-N

Molfile:  

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   37.7005   -8.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6991   -9.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7006   -6.9380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   36.2671   -9.4157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 24 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3276959

   [1-[(2-Methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-2,4-dioxopyrimidin-5-yl]methyl 3,4,5-trimethoxybenzoate

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

Calculated Properties

Molecular Weight: 460.44

Molecular Weight (Monoisotopic): 460.1482

AlogP: 1.18

#Rotatable Bonds: 8

Polar Surface Area: 135.15

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.64

CX Basic pKa: ┄

CX LogP: 1.51

CX LogD: 1.51

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: 0.15

References

1. Lee KH, Wu YS, Hall IH..  (1977)  Antitumor agents. 25. Synthesis and antitumor activity of uracil and thymine alpha-methylene-gamma-lactones and related derivatives.,  20  (7): [PMID:874966] [10.1021/jm00217a009]

Source

Source(1):

• Scientific Literature