(E,Z)-ethyl 2-cyano-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate

ID: ALA443308

Cas Number: 911843-45-3

PubChem CID: 44416395

Max Phase: Preclinical

Molecular Formula: C15H17N3O7

Molecular Weight: 351.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C(C#N)=C/c1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C15H17N3O7/c1-2-24-14(22)8(5-16)3-9-6-18(15(23)17-13(9)21)12-4-10(20)11(7-19)25-12/h3,6,10-12,19-20H,2,4,7H2,1H3,(H,17,21,23)/b8-3+/t10-,11+,12+/m0/s1

Standard InChI Key:  MYQZREIBPFMKQP-OCTANDHXSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  1  0  0  0  0  0999 V2000
   -0.6672  -23.3420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814  -23.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177  -23.7039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271  -22.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414  -22.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577  -22.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909  -24.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7262  -22.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1101  -23.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8018  -23.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5825  -24.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570  -24.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4663  -23.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033  -24.9358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5739  -23.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137  -23.7240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5521  -21.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3459  -21.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567  -20.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291  -21.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5137  -22.4728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511  -20.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740  -19.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9346  -20.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7284  -20.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 13  1  1  1
 11 14  1  6
 10 15  1  1
 15 16  1  0
  5 17  1  0
  1  2  1  0
 17 18  2  0
  1  6  1  0
 18 19  1  0
  2  3  1  0
 18 20  1  0
  3  4  1  0
 20 21  3  0
  4  5  1  0
  5  6  2  0
 19 22  1  0
 19 23  2  0
  2  7  2  0
 22 24  1  0
  4  8  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA443308

   5-[(1E)-2-Cyano-3-ethoxy-3-oxoprop-1-en-1-yl]-2'-deoxyuridine

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: 351.32

Molecular Weight (Monoisotopic): 351.1066

AlogP: -1.35

#Rotatable Bonds: 5

Polar Surface Area: 154.64

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.55

CX Basic pKa: ┄

CX LogP: -1.00

CX LogD: -1.01

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.33

Np Likeness Score: 0.17

References

1. Torrence PF, Fan X, Zhang X, Loiseau PM..  (2006)  Structurally diverse 5-substituted pyrimidine nucleosides as inhibitors of Leishmania donovani promastigotes in vitro.,  16  (19): [PMID:16879965] [10.1016/j.bmcl.2006.07.042]

2. Prichard MN, Keith KA, Johnson MP, Harden EA, McBrayer A, Luo M, Qiu S, Chattopadhyay D, Fan X, Torrence PF, Kern ER..  (2007)  Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase.,  51  (5): [PMID:17325220] [10.1128/aac.01447-06]

Source

Source(1):

• Scientific Literature