5-(6-Amino-purin-9-yl)-3-ethynyl-2-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA2094094

Chembl Id: CHEMBL2094094

Cas Number: 180300-54-3

PubChem CID: 11779021

Max Phase: Preclinical

Molecular Formula: C12H13N5O4

Molecular Weight: 291.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@@]1(O)[C@@H](CO)O[C@@H](n2cnc3c(N)ncnc32)[C@@H]1O

Standard InChI:  InChI=1S/C12H13N5O4/c1-2-12(20)6(3-18)21-11(8(12)19)17-5-16-7-9(13)14-4-15-10(7)17/h1,4-6,8,11,18-20H,3H2,(H2,13,14,15)/t6-,8+,11-,12-/m1/s1

Standard InChI Key:  VVIJADJDBPHCKC-WHNOBIIHSA-N

Alternative Forms

1. Parent:

   

   ALA2094094

   3'-c-Ethynyladenosine

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: 291.27

Molecular Weight (Monoisotopic): 291.0968

AlogP: -1.98

#Rotatable Bonds: 2

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.19

CX Basic pKa: 4.92

CX LogP: -1.94

CX LogD: -1.94

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.47

Np Likeness Score: 1.09

References

1. Tritsch D, Jung PM, Burger A, Biellmann JF..  (2000)  3'-Beta-ethynyl and 2'-deoxy-3'-beta-ethynyl adenosines: first 3'-beta-branched-adenosines substrates of adenosine deaminase.,  10  (2): [PMID:10673097] [10.1016/s0960-894x(99)00639-3]

2. Tritsch D, Jung PM, Burger A, Biellmann JF..  (2000)  3'-Beta-ethynyl and 2'-deoxy-3'-beta-ethynyl adenosines: first 3'-beta-branched-adenosines substrates of adenosine deaminase.,  10  (2): [PMID:10673097] [10.1016/s0960-894x(99)00639-3]

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. Hulpia F, Balzarini J, Schols D, Andrei G, Snoeck R, Van Calenbergh S..  (2016)  Exploring the purine core of 3'-C-ethynyladenosine (EAdo) in search of novel nucleoside therapeutics.,  26  (8): [PMID:26965865] [10.1016/j.bmcl.2016.03.005]

5. Hulpia F, Noppen S, Schols D, Andrei G, Snoeck R, Liekens S, Vervaeke P, Van Calenbergh S..  (2018)  Synthesis of a 3'-C-ethynyl-β-d-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides.,  157  [PMID:30098481] [10.1016/j.ejmech.2018.07.062]

Source

Source(1):

• Scientific Literature