4-Amino-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-ethynyl-1H-pyrimidin-2-one

ID: ALA609188

Chembl Id: CHEMBL609188

PubChem CID: 21120715

Max Phase: Preclinical

Molecular Formula: C11H13N3O5

Molecular Weight: 267.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1cn(C2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)nc1N

Standard InChI:  InChI=1S/C11H13N3O5/c1-2-5-3-14(11(18)13-9(5)12)10-8(17)7(16)6(4-15)19-10/h1,3,6-8,10,15-17H,4H2,(H2,12,13,18)/t6-,7-,8+,10?/m1/s1

Standard InChI Key:  NCZFDEBKMUJQQO-UUBZBTQISA-N

Alternative Forms

1. Parent:

   

   ALA609188

   4-amino-1-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethynylpyrimidin-2-one

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: 267.24

Molecular Weight (Monoisotopic): 267.0855

AlogP: -2.58

#Rotatable Bonds: 2

Polar Surface Area: 130.83

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.55

CX Basic pKa: ┄

CX LogP: -2.76

CX LogD: -2.76

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.43

Np Likeness Score: 0.91

References

1. Bobek M, Kavai I, Sharma RA, Grill S, Dutschman G, Cheng YC..  (1987)  Acetylenic nucleosides. 4. 1-beta-D-arabinofuranosyl-5-ethynylcytosine. Improved synthesis and evaluation of biochemical and antiviral properties.,  30  (11): [PMID:2822932] [10.1021/jm00394a039]

Source

Source(1):

• Scientific Literature