2-(4-dimethylaminomethyl-1,2,3-triazol-1-yl)-N6-methyl-9-(beta-D-ribofuranosyl)adenine

Names and Identifiers

Canonical SMILES: CNc1nc(-n2cc(CN(C)C)nn2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI: InChI=1S/C16H23N9O4/c1-17-13-10-14(20-16(19-13)25-5-8(21-22-25)4-23(2)3)24(7-18-10)15-12(28)11(27)9(6-26)29-15/h5,7,9,11-12,15,26-28H,4,6H2,1-3H3,(H,17,19,20)/t9-,11-,12-,15-/m1/s1

Standard InChI Key: CRKZMZSQJYBAJR-SDBHATRESA-N

Molfile:

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    5.1762   -3.6016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -3.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8993   -2.3633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1871   -1.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4646   -3.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4722   -2.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862   -2.0910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928   -2.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6740   -3.4321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1916   -1.1237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6078   -3.6106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6850   -4.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4909   -4.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9078   -3.8941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3594   -3.2777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -0.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118   -4.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6235   -4.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160   -5.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -5.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8892   -4.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461   -6.3340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7141   -4.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9441   -5.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935   -5.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8219   -5.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3329   -6.0262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6638   -6.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5130   -5.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  3  4  2  0
 10 16  1  0
  6  7  1  0
 17  9  1  1
 17 18  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  4  6  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
  4 10  1  0
 20 22  1  6
  5  6  2  0
 21 23  1  6
  2 11  1  0
 19 24  1  1
 11 12  1  0
 24 25  1  0
  1  2  2  0
 13 26  1  0
  5  1  1  0
 26 27  1  0
  2  3  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

Parent:

ALA374645
(2R,3R,4S,5R)-2-[2-[4-[(dimethylamino)methyl]triazol-1-yl]-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Associated Targets(Human)

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

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

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

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

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

Discover Target: ADORA2A

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

Associated Targets(non-human)

Adora3 Adenosine A3 receptor (846 Activities)

Discover Target: Adora3

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

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

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

Biocomponents

Calculated Properties

Molecular Weight: 405.42	Molecular Weight (Monoisotopic): 405.1873	AlogP: -1.88	#Rotatable Bonds: 6
Polar Surface Area: 159.50	Molecular Species: NEUTRAL	HBA: 13	HBD: 4
#RO5 Violations: 1	HBA (Lipinski): 13	HBD (Lipinski): 4	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.45	CX Basic pKa: 6.44	CX LogP: -1.38	CX LogD: -1.43
Aromatic Rings: 3	Heavy Atoms: 29	QED Weighted: 0.36	Np Likeness Score: -0.25

References

1. Cosyn L, Palaniappan KK, Kim SK, Duong HT, Gao ZG, Jacobson KA, Van Calenbergh S.. (2006) 2-triazole-substituted adenosines: a new class of selective A3 adenosine receptor agonists, partial agonists, and antagonists., 49 (25): [PMID:17149867] [10.1021/jm0608208]

Source

Source(1):

Scientific Literature