2-{6-Amino-2-[2-(4-chloro-phenyl)-ethoxy]-purin-9-yl}-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA2311197

PubChem CID: 71720352

Max Phase: Preclinical

Molecular Formula: C18H20ClN5O5

Molecular Weight: 421.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(OCCc2ccc(Cl)cc2)nc2c1ncn2[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H20ClN5O5/c19-10-3-1-9(2-4-10)5-6-28-18-22-15(20)12-16(23-18)24(8-21-12)17-14(27)13(26)11(7-25)29-17/h1-4,8,11,13-14,17,25-27H,5-7H2,(H2,20,22,23)/t11-,13-,14-,17-/m0/s1

Standard InChI Key:  WUCQGGOGHZRELS-MJFSBKNWSA-N

Molfile:  

     RDKit          2D

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    5.1410   -1.9619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3962   -1.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1410   -3.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3962   -0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6963   -2.1377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1410   -0.6655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5858   -4.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6203   -1.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -0.9068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2995   -3.0757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6963   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -1.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0029   -4.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374   -3.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1100   -5.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6963    0.2965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -2.1240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4719   -5.3548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930   -0.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374   -3.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276   -1.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0067   -0.4483    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999   -1.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758   -0.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861   -2.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1379   -0.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5551   -1.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2959   -3.0757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413   -2.1137    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
 17 12  1  0
 13 18  1  6
 19 24  2  0
 14 20  1  1
 21 29  1  0
 22 19  1  0
 23 25  2  0
 24 26  1  0
 25 21  1  0
 26 21  2  0
 27 17  1  0
 28 20  1  0
 29 27  1  0
  4  6  1  0
 13 14  1  0
 11  9  2  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2311197

   (2S,3S,4R,5S)-2-[6-amino-2-[2-(4-chlorophenyl)ethoxy]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

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

Calculated Properties

Molecular Weight: 421.84

Molecular Weight (Monoisotopic): 421.1153

AlogP: 0.29

#Rotatable Bonds: 6

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: 4.21

CX LogP: 1.05

CX LogD: 1.05

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: 0.47

References

1. Ueeda M, Thompson RD, Arroyo LH, Olsson RA..  (1991)  2-aralkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.,  34  (4): [PMID:2016708] [10.1021/jm00108a015]

Source

Source(1):

• Scientific Literature