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

Names and Identifiers

Canonical SMILES: COc1nc(N)c2ncn([C@H]3O[C@@H](CO)[C@H](O)[C@@H]3O)c2n1

Standard InChI: InChI=1S/C11H15N5O5/c1-20-11-14-8(12)5-9(15-11)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7-,10-/m0/s1

Standard InChI Key: AJACDNCVEGIBNA-DEGSGYPDSA-N

Molfile:

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.8901    4.5225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1420    4.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901    2.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1420    5.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645    4.3459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901    5.8247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369    1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710    5.5823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0538    3.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645    5.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710    4.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7603    1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    2.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381    1.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645    6.7910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2452    1.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9913    4.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    3.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0590    3.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    4.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  1
  4  2  2  0
  5  2  1  0
  6  8  2  0
  7  3  1  0
  8  1  1  0
  9 12  1  0
 10  3  1  0
 11  4  1  0
 12  5  2  0
 13  7  1  0
 14 10  1  0
  7 15  1  6
 16 11  1  0
 13 17  1  6
 18 12  1  0
 14 19  1  1
 20 19  1  0
 21 18  1  0
  4  6  1  0
 13 14  1  0
 11  9  2  0
M  END

Alternative Forms

Parent:

ALA2311198
(2S,3S,4R,5S)-2-(6-amino-2-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Associated Targets(Human)

ADORA2B Tclin Adenosine A2 receptor (1064 Activities)

Discover Target: ADORA2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine receptors; A1 & A2 (188 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ADORA1 Adenosine A1 receptor (540 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Molecule Features

Natural Product: Yes	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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 297.27	Molecular Weight (Monoisotopic): 297.1073	AlogP: -1.97	#Rotatable Bonds: 3
Polar Surface Area: 148.77	Molecular Species: NEUTRAL	HBA: 10	HBD: 4
#RO5 Violations: ┄	HBA (Lipinski): 10	HBD (Lipinski): 5	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 12.45	CX Basic pKa: 4.25	CX LogP: -1.57	CX LogD: -1.57
Aromatic Rings: 2	Heavy Atoms: 21	QED Weighted: 0.51	Np Likeness Score: 1.03

References

1. Ueeda M, Thompson RD, Arroyo LH, Olsson RA.. (1991) 2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor., 34 (4): [PMID:2016707] [10.1021/jm00108a014]

Source

Source(1):

Scientific Literature