1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (beta-lyxoU)

ID: ALA2093066

Chembl Id: CHEMBL2093066

Cas Number: 4348-61-2

PubChem CID: 9859650

Max Phase: Preclinical

Molecular Formula: C9H12N2O6

Molecular Weight: 244.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1ccn([C@@H]2O[C@H](CO)[C@H](O)[C@@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6+,7+,8-/m1/s1

Standard InChI Key:  DRTQHJPVMGBUCF-YDKYIBAVSA-N

Alternative Forms

1. Parent:

   

   ALA2093066

   1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furyl]pyrimidine-2,4(1H,3H)-dione

Molecule Features

Natural Product: Yes

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: 244.20

Molecular Weight (Monoisotopic): 244.0695

AlogP: -2.85

#Rotatable Bonds: 2

Polar Surface Area: 124.78

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: ┄

CX LogP: -2.42

CX LogD: -2.42

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.44

Np Likeness Score: 1.49

References

1. Gosselin G, Bergogne MC, De Rudder J, De Clercq E, Imbach JL..  (1987)  Systematic synthesis and biological evaluation of alpha- and beta-D-lyxofuranosyl nucleosides of the five naturally occurring nucleic acid bases.,  30  (6): [PMID:3585910] [10.1021/jm00389a005]

2. Focher F, Lossani A, Verri A, Spadari S, Maioli A, Gambino JJ, Wright GE, Eberle R, Black DH, Medveczky P, Medveczky M, Shugar D..  (2007)  Sensitivity of monkey B virus (Cercopithecine herpesvirus 1) to antiviral drugs: role of thymidine kinase in antiviral activities of substrate analogs and acyclonucleosides.,  51  (6): [PMID:17438061] [10.1128/aac.01284-06]

Source

Source(1):

• Scientific Literature