4-Amino-1-((2R,3R,4R,5R)-3-ethynyl-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

ID: ALA98778

Cas Number: 188413-99-2

PubChem CID: 10515947

Max Phase: Preclinical

Molecular Formula: C11H13N3O5

Molecular Weight: 267.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc(N)nc1=O

Standard InChI:  InChI=1S/C11H13N3O5/c1-2-11(18)8(16)6(5-15)19-9(11)14-4-3-7(12)13-10(14)17/h1,3-4,6,8-9,15-16,18H,5H2,(H2,12,13,17)/t6-,8-,9-,11-/m1/s1

Standard InChI Key:  LMPQMWCSENOFHW-PNHWDRBUSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   14.8115    3.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9919    3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5064    3.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7550    2.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5400    2.2446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0865    2.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5301    1.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4198    2.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6771    3.2963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6310    2.2586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4576    1.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0690    0.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6686    1.2051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0575    1.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2727    1.5086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2349    2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0238    2.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6365    1.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1860    0.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  3  9  1  0
  8 10  1  6
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10 17  1  0
 18 19  3  0
  6 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA98778

   2'-ETHYNYL-D-CYTIDINE

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: 267.24

Molecular Weight (Monoisotopic): 267.0855

AlogP: -2.56

#Rotatable Bonds: 2

Polar Surface Area: 130.83

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.96

CX Basic pKa: ┄

CX LogP: -2.65

CX LogD: -2.65

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.43

Np Likeness Score: 1.39

References

1. Hattori H, Nozawa E, Iino T, Yoshimura Y, Shuto S, Shimamoto Y, Nomura M, Fukushima M, Tanaka M, Sasaki T, Matsuda A..  (1998)  Nucleosides and nucleotides. 175. Structural requirements of the sugar moiety for the antitumor activities of new nucleoside antimetabolites, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine and -uracil1.,  41  (15): [PMID:9667977] [10.1021/jm9801814]

2. Tonelli M, Simone M, Tasso B, Novelli F, Boido V, Sparatore F, Paglietti G, Pricl S, Giliberti G, Blois S, Ibba C, Sanna G, Loddo R, La Colla P..  (2010)  Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives.,  18  (8): [PMID:20359898] [10.1016/j.bmc.2010.02.037]

3. Chen YL, Yin Z, Duraiswamy J, Schul W, Lim CC, Liu B, Xu HY, Qing M, Yip A, Wang G, Chan WL, Tan HP, Lo M, Liung S, Kondreddi RR, Rao R, Gu H, He H, Keller TH, Shi PY..  (2010)  Inhibition of dengue virus RNA synthesis by an adenosine nucleoside.,  54  (7): [PMID:20457821] [10.1128/aac.00140-10]

4. Carta A, Briguglio I, Piras S, Corona P, Boatto G, Nieddu M, Giunchedi P, Marongiu ME, Giliberti G, Iuliano F, Blois S, Ibba C, Busonera B, La Colla P..  (2011)  Quinoline tricyclic derivatives. Design, synthesis and evaluation of the antiviral activity of three new classes of RNA-dependent RNA polymerase inhibitors.,  19  (23): [PMID:22047799] [10.1016/j.bmc.2011.10.009]

5. Vitale G, Corona P, Loriga M, Carta A, Paglietti G, Giliberti G, Sanna G, Farci P, Marongiu ME, La Colla P..  (2012)  5-acetyl-2-arylbenzimidazoles as antiviral agents. Part 4.,  53  [PMID:22513121] [10.1016/j.ejmech.2012.03.038]

6. Bielenica A, Kossakowski J, Struga M, Dybaa I, La Colla P, Tamburini E, Loddo R.  (2011)  Biological evaluation of novel 1,4-dithiine derivatives as potential antimicrobial agents,  20  (8): [10.1007/s00044-010-9513-0]

7. Upadhyay K, Manvar A, Loddo R, Colla PL, Virsodiya V, Trivedi J, Chaniyara R, Shah A.  (2013)  Syntheses and in vitro biological screening of 1-aryl-10H-[1,2,4]triazolo[3,4:3,4][1,2,4]triazino[5,6-b]indoles,  22  (8): [10.1007/s00044-012-0342-1]

8. Loddo R, Briguglio I, Corona P, Piras S, Loriga M, Paglietti G, Carta A, Sanna G, Giliberti G, Ibba C, Farci P, La Colla P..  (2014)  Synthesis and antiviral activity of new phenylimidazopyridines and N-benzylidenequinolinamines derived by molecular simplification of phenylimidazo[4,5-g]quinolines.,  84  [PMID:25014745] [10.1016/j.ejmech.2014.07.011]

9. Loddo R, Novelli F, Sparatore A, Tasso B, Tonelli M, Boido V, Sparatore F, Collu G, Delogu I, Giliberti G, La Colla P..  (2015)  Antiviral activity of benzotriazole derivatives. 5-[4-(Benzotriazol-2-yl)phenoxy]-2,2-dimethylpentanoic acids potently and selectively inhibit Coxsackie Virus B5.,  23  (21): [PMID:26443549] [10.1016/j.bmc.2015.09.035]

10. Briguglio I, Loddo R, Laurini E, Fermeglia M, Piras S, Corona P, Giunchedi P, Gavini E, Sanna G, Giliberti G, Ibba C, Farci P, La Colla P, Pricl S, Carta A..  (2015)  Synthesis, cytotoxicity and antiviral evaluation of new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives.,  105  [PMID:26479028] [10.1016/j.ejmech.2015.10.002]

11. Carta A, Briguglio I, Piras S, Corona P, Ibba R, Laurini E, Fermeglia M, Pricl S, Desideri N, Atzori EM, La Colla P, Collu G, Delogu I, Loddo R..  (2016)  A combined in silico/in vitro approach unveils common molecular requirements for efficient BVDV RdRp binding of linear aromatic N-polycyclic systems.,  117  [PMID:27161176] [10.1016/j.ejmech.2016.03.080]

Source

Source(1):

• Scientific Literature