((2S,3S,4R,5R)-5-(5-azido-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methylphosphonate

ID: ALA1765125

Chembl Id: CHEMBL1765125

PubChem CID: 54582224

Max Phase: Preclinical

Molecular Formula: C9H12N5O8P

Molecular Weight: 349.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=Nc1cn([C@@H]2O[C@H](CP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C9H12N5O8P/c10-13-12-3-1-14(9(18)11-7(3)17)8-6(16)5(15)4(22-8)2-23(19,20)21/h1,4-6,8,15-16H,2H2,(H,11,17,18)(H2,19,20,21)/t4-,5-,6-,8-/m1/s1

Standard InChI Key:  KKPFMFPIJFGKPJ-UAKXSSHOSA-N

Alternative Forms

1. Parent:

   

   ALA1765125

   [(2S,3S,4R,5R)-5-(5-azido-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methylphosphonic acid

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: 349.20

Molecular Weight (Monoisotopic): 349.0423

AlogP: -1.72

#Rotatable Bonds: 4

Polar Surface Area: 210.84

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -10.50

CX Basic pKa: ┄

CX LogP: -2.93

CX LogD: -5.38

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.18

Np Likeness Score: 0.70

References

1. Lewis M, Meza-Avina ME, Wei L, Crandall IE, Bello AM, Poduch E, Liu Y, Paige CJ, Kain KC, Pai EF, Kotra LP..  (2011)  Novel interactions of fluorinated nucleotide derivatives targeting orotidine 5'-monophosphate decarboxylase.,  54  (8): [PMID:21417464] [10.1021/jm101642g]

Source

Source(1):

• Scientific Literature