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

ID: ALA3144361

Chembl Id: CHEMBL3144361

Cas Number: 507232-22-6

PubChem CID: 10092318

Max Phase: Preclinical

Molecular Formula: C9H10IN3O7

Molecular Weight: 399.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O[N+](=O)[O-])[C@@H](CO)O2)cc1I

Standard InChI:  InChI=1S/C9H10IN3O7/c10-4-2-12(9(16)11-8(4)15)7-1-5(20-13(17)18)6(3-14)19-7/h2,5-7,14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

Standard InChI Key:  WZYDJRJDUGXQTO-RRKCRQDMSA-N

Alternative Forms

1. Parent:

   

   ALA3144361

   [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-iodo-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: 399.10

Molecular Weight (Monoisotopic): 398.9563

AlogP: -1.00

#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: 8.46

CX Basic pKa: ┄

CX LogP: 0.17

CX LogD: 0.13

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.38

Np Likeness Score: 0.29

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