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

ID: ALA318896

Chembl Id: CHEMBL318896

PubChem CID: 10754286

Max Phase: Preclinical

Molecular Formula: C11H13N3O5

Molecular Weight: 267.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)[C@@H](CO)O[C@@H](n2ccc(N)nc2=O)[C@@H]1O

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

Standard InChI Key:  JFIWEPHGRUDAJN-YNCDLQQUSA-N

Alternative Forms

1. Parent:

   

   ALA318896

   4-amino-1-[(2R,3R,4R,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-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: -2.56

#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: 11.21

CX Basic pKa: ┄

CX LogP: -2.65

CX LogD: -2.65

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.43

Np Likeness Score: 1.37

References

1. Hattori H, Nozawa E, Iino T, Yoshimura Y, Shuto S, Shimamoto Y, Nomura M, Fukushima M, Tanaka M, Sasaki T, Matsuda A..  (1998)  Nucleosides and nucleotides. 175. Structural requirements of the sugar moiety for the antitumor activities of new nucleoside antimetabolites, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine and -uracil1.,  41  (15): [PMID:9667977] [10.1021/jm9801814]

2. Hattori H, Nozawa E, Iino T, Yoshimura Y, Shuto S, Shimamoto Y, Nomura M, Fukushima M, Tanaka M, Sasaki T, Matsuda A..  (1998)  Nucleosides and nucleotides. 175. Structural requirements of the sugar moiety for the antitumor activities of new nucleoside antimetabolites, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine and -uracil1.,  41  (15): [PMID:9667977] [10.1021/jm9801814]

3. Hattori H, Tanaka M, Fukushima M, Sasaki T, Matsuda A..  (1996)  Nucleosides and nucleotides. 158. 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)-cytosine, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil, and their nucleobase analogues as new potential multifunctional antitumor nucleosides with a broad spectrum of activity.,  39  (25): [PMID:8960561] [10.1021/jm960537g]

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays