5-(6-Amino-2-ethynyl-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide

ID: ALA2113449

Chembl Id: CHEMBL2113449

PubChem CID: 9996838

Max Phase: Preclinical

Molecular Formula: C14H16N6O4

Molecular Weight: 332.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1nc(N)c2ncn([C@@H]3O[C@H](C(=O)NCC)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C14H16N6O4/c1-3-6-18-11(15)7-12(19-6)20(5-17-7)14-9(22)8(21)10(24-14)13(23)16-4-2/h1,5,8-10,14,21-22H,4H2,2H3,(H,16,23)(H2,15,18,19)/t8-,9+,10-,14+/m0/s1

Standard InChI Key:  WSLFXMBRRBTFCE-AEISUSGSSA-N

Alternative Forms

1. Parent:

   

   ALA2113449

   (2S,3S,4R,5R)-5-(6-amino-2-ethynylpurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide

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: 332.32

Molecular Weight (Monoisotopic): 332.1233

AlogP: -1.85

#Rotatable Bonds: 3

Polar Surface Area: 148.41

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.39

CX Basic pKa: 4.03

CX LogP: -1.12

CX LogD: -1.12

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.48

Np Likeness Score: 0.29

References

1. Cristalli G, Camaioni E, Vittori S, Volpini R, Borea PA, Conti A, Dionisotti S, Ongini E, Monopoli A..  (1995)  2-Aralkynyl and 2-heteroalkynyl derivatives of adenosine-5'-N-ethyluronamide as selective A2a adenosine receptor agonists.,  38  (9): [PMID:7739005] [10.1021/jm00009a007]

2. Cristalli G, Volpini R, Vittori S, Camaioni E, Monopoli A, Conti A, Dionisotti S, Zocchi C, Ongini E..  (1994)  2-Alkynyl derivatives of adenosine-5'-N-ethyluronamide: selective A2 adenosine receptor agonists with potent inhibitory activity on platelet aggregation.,  37  (11): [PMID:8201607] [10.1021/jm00037a024]

Source

Source(1):

• Scientific Literature