cis-Ethyl-(3SR,5RS)-5-[4-(acetylamino)-2-oxopyrimidin-1(2H)-yl]-3-(diethoxyphosphoryl)-2-methylisoxazolidine-5-carboxylate

ID: ALA2035676

Chembl Id: CHEMBL2035676

PubChem CID: 70694358

Max Phase: Preclinical

Molecular Formula: C17H27N4O8P

Molecular Weight: 446.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@@]1(n2ccc(NC(C)=O)nc2=O)C[C@H](P(=O)(OCC)OCC)N(C)O1

Standard InChI:  InChI=1S/C17H27N4O8P/c1-6-26-15(23)17(21-10-9-13(18-12(4)22)19-16(21)24)11-14(20(5)29-17)30(25,27-7-2)28-8-3/h9-10,14H,6-8,11H2,1-5H3,(H,18,19,22,24)/t14-,17+/m0/s1

Standard InChI Key:  LRDTWQCXMAMFPR-WMLDXEAASA-N

Alternative Forms

1. Parent:

   

   ALA2035676

   ethyl (3S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-3-diethoxyphosphoryl-2-methyl-1,2-oxazolidine-5-carboxylate

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: 446.40

Molecular Weight (Monoisotopic): 446.1567

AlogP: 1.28

#Rotatable Bonds: 9

Polar Surface Area: 138.29

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.20

CX Basic pKa: ┄

CX LogP: 0.80

CX LogD: 0.80

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -0.32

References

1. Romeo R, Carnovale C, Giofrè SV, Romeo G, Macchi B, Frezza C, Marino-Merlo F, Pistarà V, Chiacchio U..  (2012)  Truncated phosphonated C-1'-branched N,O-nucleosides: a new class of antiviral agents.,  20  (11): [PMID:22549138] [10.1016/j.bmc.2012.03.047]

Source

Source(1):

• Scientific Literature