1-(5-Hydroxymethyl-4-nitrooxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

ID: ALA3144334

Chembl Id: CHEMBL3144334

Cas Number: 77421-84-2

PubChem CID: 11119722

Max Phase: Preclinical

Molecular Formula: C10H13N3O7

Molecular Weight: 287.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](O[N+](=O)[O-])[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H13N3O7/c1-5-3-12(10(16)11-9(5)15)8-2-6(20-13(17)18)7(4-14)19-8/h3,6-8,14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1

Standard InChI Key:  IETUTDWZXUFCPZ-XLPZGREQSA-N

Alternative Forms

1. Parent:

   

   ALA3144334

   [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] nitrate

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: 287.23

Molecular Weight (Monoisotopic): 287.0753

AlogP: -1.30

#Rotatable Bonds: 4

Polar Surface Area: 136.69

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: -0.42

CX LogD: -0.42

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.52

Np Likeness Score: 0.39

References

1. Naimi E, Zhou A, Khalili P, Wiebe LI, Balzarini J, De Clercq E, Knaus EE..  (2003)  Synthesis of 3'- and 5'-nitrooxy pyrimidine nucleoside nitrate esters: "nitric oxide donor" agents for evaluation as anticancer and antiviral agents.,  46  (6): [PMID:12620076] [10.1021/jm020299r]

Source

Source(1):

• Scientific Literature