5-[6-Amino-2-(3-hydroxy-3-phenyl-but-1-ynyl)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide

ID: ALA2113399

Chembl Id: CHEMBL2113399

PubChem CID: 10003996

Max Phase: Preclinical

Molecular Formula: C22H24N6O5

Molecular Weight: 452.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)nc(C#CC(C)(O)c4ccccc4)nc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C22H24N6O5/c1-3-24-20(31)17-15(29)16(30)21(33-17)28-11-25-14-18(23)26-13(27-19(14)28)9-10-22(2,32)12-7-5-4-6-8-12/h4-8,11,15-17,21,29-30,32H,3H2,1-2H3,(H,24,31)(H2,23,26,27)/t15-,16+,17-,21+,22?/m0/s1

Standard InChI Key:  YUGNPNQJJOBKPP-CPJKPBJPSA-N

Alternative Forms

1. Parent:

   

   ALA2113399

   (2S,3S,4R,5R)-5-[6-amino-2-(3-hydroxy-3-phenylbut-1-ynyl)purin-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: 452.47

Molecular Weight (Monoisotopic): 452.1808

AlogP: -0.58

#Rotatable Bonds: 4

Polar Surface Area: 168.64

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.13

CX Basic pKa: 3.84

CX LogP: 0.28

CX LogD: 0.28

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 0.21

References

1. 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