1-((3R,4R)-4-Ethynyl-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA317514

Chembl Id: CHEMBL317514

PubChem CID: 15332148

Max Phase: Preclinical

Molecular Formula: C11H12N2O6

Molecular Weight: 268.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)[C@@H](CO)O[C@@H](n2ccc(=O)[nH]c2=O)[C@@H]1O

Standard InChI:  InChI=1S/C11H12N2O6/c1-2-11(18)6(5-14)19-9(8(11)16)13-4-3-7(15)12-10(13)17/h1,3-4,6,8-9,14,16,18H,5H2,(H,12,15,17)/t6-,8+,9-,11+/m1/s1

Standard InChI Key:  KNGMLOFYXFWJLZ-YNCDLQQUSA-N

Alternative Forms

1. Parent:

   

   ALA317514

   1-[(2R,3R,4R,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

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: 268.23

Molecular Weight (Monoisotopic): 268.0695

AlogP: -2.85

#Rotatable Bonds: 2

Polar Surface Area: 124.78

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.69

CX Basic pKa: ┄

CX LogP: -2.26

CX LogD: -2.27

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.43

Np Likeness Score: 1.23

References

1. Matsuda A, Hattori H, Tanaka M, Sasaki T.  (1996)  Nucleosides and nucleotides. 152. 1-(3-C-Ethynyl--D-ribo-pentofuranosyl)uracil as a broad spectrum antitumor nucleoside,  6  (16): [10.1016/0960-894X(96)00339-3]

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, 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]

4. 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]

5. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays