5-(Perylen-3-yl)ethynyl-arabino-uridine

ID: ALA3797928

Chembl Id: CHEMBL3797928

PubChem CID: 52914323

Max Phase: Preclinical

Molecular Formula: C31H22N2O6

Molecular Weight: 518.53

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)cc1C#Cc1ccc2c3cccc4cccc(c5cccc1c52)c43

Standard InChI:  InChI=1S/C31H22N2O6/c34-15-24-27(35)28(36)30(39-24)33-14-18(29(37)32-31(33)38)11-10-16-12-13-23-21-8-2-5-17-4-1-7-20(25(17)21)22-9-3-6-19(16)26(22)23/h1-9,12-14,24,27-28,30,34-36H,15H2,(H,32,37,38)/t24-,27-,28+,30-/m1/s1

Standard InChI Key:  QMGZCFXCMATIAO-FKGPWWPUSA-N

Associated Targets(Human)

RD (1212 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Human alphaherpesvirus 1 (11089 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human alphaherpesvirus 2 (4932 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Maize chlorotic mottle virus (6 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vesicular stomatitis virus (4460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sindbis virus (1599 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hepatitis C virus (23859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Influenza A virus (11224 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tick-borne encephalitis virus (132 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterovirus A71 (1246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Murid betaherpesvirus 1 (143 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Poliovirus 1 (1274 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Echovirus (56 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

Calculated Properties

Molecular Weight: 518.53Molecular Weight (Monoisotopic): 518.1478AlogP: 2.60#Rotatable Bonds: 2
Polar Surface Area: 124.78Molecular Species: NEUTRALHBA: 7HBD: 4
#RO5 Violations: 1HBA (Lipinski): 8HBD (Lipinski): 4#RO5 Violations (Lipinski): 1
CX Acidic pKa: 9.43CX Basic pKa: CX LogP: 2.89CX LogD: 2.88
Aromatic Rings: 6Heavy Atoms: 39QED Weighted: 0.16Np Likeness Score: 0.48

References

1. Orlov AA, Chistov AA, Kozlovskaya LI, Ustinov AV, Korshun VA, Karganova GG, Osolodkin DI.  (2016)  Rigid amphipathic nucleosides suppress reproduction of the tick-borne encephalitis virus,  (3): [10.1039/C5MD00538H]
2. Chistov AA, Orlov AA, Streshnev PP, Slesarchuk NA, Aparin IO, Rathi B, Brylev VA, Kutyakov SV, Mikhura IV, Ustinov AV, Westman G, Palyulin VA, Jain N, Osolodkin DI, Kozlovskaya LI, Korshun VA..  (2019)  Compounds based on 5-(perylen-3-ylethynyl)uracil scaffold: High activity against tick-borne encephalitis virus and non-specific activity against enterovirus A.,  171  [PMID:30909022] [10.1016/j.ejmech.2019.03.029]
3. Slesarchuk NA, Khvatov EV, Chistov AA, Proskurin GV, Nikitin TD, Lazarevich AI, Ulanovskaya AA, Ulashchik EA, Orlov AA, Jegorov AV, Ustinov AV, Tyurin AP, Shmanai VV, Ishmukhametov AA, Korshun VA, Osolodkin DI, Kozlovskaya LI, Aralov AV..  (2020)  Simplistic perylene-related compounds as inhibitors of tick-borne encephalitis virus reproduction.,  30  (10): [PMID:32199731] [10.1016/j.bmcl.2020.127100]

Source