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

ID: ALA2311199

PubChem CID: 71716086

Max Phase: Preclinical

Molecular Formula: C19H23N5O5

Molecular Weight: 401.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(OCCCc2ccccc2)nc2c1ncn2[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H23N5O5/c20-16-13-17(24(10-21-13)18-15(27)14(26)12(9-25)29-18)23-19(22-16)28-8-4-7-11-5-2-1-3-6-11/h1-3,5-6,10,12,14-15,18,25-27H,4,7-9H2,(H2,20,22,23)/t12-,14-,15-,18-/m0/s1

Standard InChI Key:  UDWLAWJOABGYPL-OWCBBSPXSA-N

Molfile:  

     RDKit          2D

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   21.0338  -13.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7771  -15.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0338  -12.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3353  -13.5452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7771  -12.0759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2210  -16.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2553  -12.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6230  -12.3168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9332  -14.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3353  -11.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6230  -13.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6352  -16.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0687  -15.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7461  -16.7728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3353  -11.1159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1031  -16.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9108  -13.5314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0687  -14.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0583  -13.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9255  -14.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1985  -13.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7739  -13.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3494  -13.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0514  -14.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4862  -13.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3391  -14.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6338  -13.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6268  -14.3263    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 23  1  0
 21 19  1  0
 22 18  1  0
 23 26  1  0
 24 20  2  0
 25 20  1  0
 26 22  1  0
 27 25  2  0
 28 24  1  0
 29 27  1  0
  6  4  1  0
 14 13  1  0
  9 11  2  0
 29 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2311199

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

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: 401.42

Molecular Weight (Monoisotopic): 401.1699

AlogP: 0.03

#Rotatable Bonds: 7

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: 4.22

CX LogP: 0.89

CX LogD: 0.89

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: 0.62

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