5-(1-Azido-2-chloro-ethyl)-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA3142423

Chembl Id: CHEMBL3142423

PubChem CID: 488247

Max Phase: Preclinical

Molecular Formula: C11H14ClN5O5

Molecular Weight: 331.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=NC(CCl)c1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C11H14ClN5O5/c12-2-6(15-16-13)5-3-17(11(21)14-10(5)20)9-1-7(19)8(4-18)22-9/h3,6-9,18-19H,1-2,4H2,(H,14,20,21)/t6?,7-,8+,9+/m0/s1

Standard InChI Key:  UCPSBDUPEGUDEU-GSLILNRNSA-N

Alternative Forms

1. Parent:

   

   ALA3142423

   5-(1-Azido-2-chloroethyl)-2'-deoxyuridine

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: 331.72

Molecular Weight (Monoisotopic): 331.0683

AlogP: -0.23

#Rotatable Bonds: 5

Polar Surface Area: 153.31

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.76

CX Basic pKa: ┄

CX LogP: -0.86

CX LogD: -0.97

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.29

Np Likeness Score: 0.77

References

1. Kumar R, Wiebe LI, Knaus EE..  (1993)  Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.,  36  (17): [PMID:8394933] [10.1021/jm00069a004]

2. Kumar R, Rai D, Sharma SK, Saffran HA, Blush R, Tyrrell DL..  (2001)  Synthesis and antiviral activity of novel 5-(1-cyanamido-2-haloethyl) and 5-(1-hydroxy(or methoxy)-2-azidoethyl) analogues of uracil nucleosides.,  44  (21): [PMID:11585457] [10.1021/jm010226s]

3. Kumar R, Sharma N, Nath M, Saffran HA, Tyrrell DL..  (2001)  Synthesis and antiviral activity of novel acyclic nucleoside analogues of 5-(1-azido-2-haloethyl)uracils.,  44  (24): [PMID:11708924] [10.1021/jm010227k]

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays