5-(Perylen-3-yl)ethynyl-2'-deoxy-uridine

ID: ALA3798024

Chembl Id: CHEMBL3798024

Cas Number: 639509-22-1

PubChem CID: 24771429

Max Phase: Preclinical

Molecular Formula: C31H22N2O5

Molecular Weight: 502.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1C#Cc1ccc2c3cccc4cccc(c5cccc1c52)c43

Standard InChI:  InChI=1S/C31H22N2O5/c34-16-26-25(35)14-27(38-26)33-15-19(30(36)32-31(33)37)11-10-17-12-13-24-22-8-2-5-18-4-1-7-21(28(18)22)23-9-3-6-20(17)29(23)24/h1-9,12-13,15,25-27,34-35H,14,16H2,(H,32,36,37)/t25-,26+,27+/m0/s1

Standard InChI Key:  RKXFQGZIGHUJCW-OYUWMTPXSA-N

Alternative Forms

1. Parent:

   

   ALA3798024

   2'-Deoxy-5-[(perylen-3-yl)ethynyl]uridine

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: 502.53

Molecular Weight (Monoisotopic): 502.1529

AlogP: 3.63

#Rotatable Bonds: 2

Polar Surface Area: 104.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.44

CX Basic pKa:

CX LogP: 3.79

CX LogD: 3.78

Aromatic Rings: 6

Heavy Atoms: 38

QED Weighted: 0.19

Np Likeness Score: 0.37

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,  7  (3): [10.1039/C5MD00538H]

2. Proskurin GV, Orlov AA, Brylev VA, Kozlovskaya LI, Chistov AA, Karganova GG, Palyulin VA, Osolodkin DI, Korshun VA, Aralov AV..  (2018)  3'-O-Substituted 5-(perylen-3-ylethynyl)-2'-deoxyuridines as tick-borne encephalitis virus reproduction inhibitors.,  155  [PMID:29859999] [10.1016/j.ejmech.2018.05.040]

3. 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]

Source

Source(1):

• Scientific Literature