5'-Methyl-5'-[(5-cinnamoyloxymethyl)uracil-1-ylmethyl]-2'-oxo-3'-methylenetetrahydrofuran

ID: ALA3276958

PubChem CID: 12381710

Max Phase: Preclinical

Molecular Formula: C21H20N2O6

Molecular Weight: 396.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC(C)(Cn2cc(COC(=O)/C=C/c3ccccc3)c(=O)[nH]c2=O)OC1=O

Standard InChI:  InChI=1S/C21H20N2O6/c1-14-10-21(2,29-19(14)26)13-23-11-16(18(25)22-20(23)27)12-28-17(24)9-8-15-6-4-3-5-7-15/h3-9,11H,1,10,12-13H2,2H3,(H,22,25,27)/b9-8+

Standard InChI Key:  VDXSTHQVVRXBFH-CMDGGOBGSA-N

Molfile:  

     RDKit          2D

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   28.0212   -2.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7333   -2.5793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4453   -2.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4453   -1.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7333   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7333   -0.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3074   -2.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1610   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7333   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0188   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2650   -3.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7129   -4.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1256   -4.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9324   -4.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8925   -4.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7900   -5.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7296   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8743   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5900   -0.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3032   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5924   -0.1146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0189   -0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7322   -1.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7245   -2.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4369   -2.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1536   -2.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1534   -1.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4403   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  2  3  1  0
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  3 10  1  0
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 15 11  1  0
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 11 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
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 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3276958

   [1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-2,4-dioxopyrimidin-5-yl]methyl (E)-3-phenylprop-2-enoate

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: 396.40

Molecular Weight (Monoisotopic): 396.1321

AlogP: 1.55

#Rotatable Bonds: 6

Polar Surface Area: 107.46

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.64

CX Basic pKa: ┄

CX LogP: 2.52

CX LogD: 2.52

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: 0.24

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