2'-ETHYNYL-D-CYTIDINE

ID: ALA98778

Max Phase: Preclinical

Molecular Formula: C11H13N3O5

Molecular Weight: 267.24

Molecule Type: Small molecule

Associated Items:

Representations

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

Associated Targets(Human)

KB 17409 Activities

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MT4 17854 Activities

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A549 127892 Activities

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Associated Targets(non-human)

L1210 27553 Activities

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Poliovirus 1 1274 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Coxsackievirus B2 343 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Yellow fever virus 1530 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Bovine viral diarrhea virus 1 1277 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Vero 26788 Activities

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Vaccinia virus 4609 Activities

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Respiratory syncytial virus 3434 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Human alphaherpesvirus 1 11089 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

dengue virus type 2 2400 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Coxsackievirus B5 476 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Human poliovirus 1 strain Sabin 65 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Human orthopneumovirus 392 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Human immunodeficiency virus 1 70413 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

West Nile virus 623 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Vesicular stomatitis virus 4460 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 267.24Molecular Weight (Monoisotopic): 267.0855AlogP: -2.56#Rotatable Bonds: 2
Polar Surface Area: 130.83Molecular Species: NEUTRALHBA: 8HBD: 4
#RO5 Violations: 0HBA (Lipinski): 8HBD (Lipinski): 5#RO5 Violations (Lipinski): 0
CX Acidic pKa: 10.96CX Basic pKa: CX LogP: -2.65CX LogD: -2.65
Aromatic Rings: 1Heavy Atoms: 19QED Weighted: 0.43Np 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]

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