4-Amino-1-(5-hydroxymethyl-4-nitrooxy-tetrahydro-furan-2-yl)-5-iodo-1H-pyrimidin-2-one

ID: ALA3143977

Chembl Id: CHEMBL3143977

PubChem CID: 10916312

Max Phase: Preclinical

Molecular Formula: C9H11IN4O6

Molecular Weight: 398.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n([C@H]2C[C@H](O[N+](=O)[O-])[C@@H](CO)O2)cc1I

Standard InChI:  InChI=1S/C9H11IN4O6/c10-4-2-13(9(16)12-8(4)11)7-1-5(20-14(17)18)6(3-15)19-7/h2,5-7,15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1

Standard InChI Key:  HRDXGNISVLWZCO-RRKCRQDMSA-N

Alternative Forms

1. Parent:

   

   ALA3143977

   [(2R,3S,5R)-5-(4-amino-5-iodo-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)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: 398.11

Molecular Weight (Monoisotopic): 397.9723

AlogP: -0.71

#Rotatable Bonds: 4

Polar Surface Area: 142.74

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.21

CX LogD: -0.21

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.38

Np Likeness Score: 0.34

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