9-alpha-D-Arabinofuranosyl-2-methoxyadenine

ID: ALA3248868

PubChem CID: 90673512

Max Phase: Preclinical

Molecular Formula: C11H15N5O5

Molecular Weight: 297.27

Molecule Type: Small molecule

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+/m1/s1

Standard InChI Key:  AJACDNCVEGIBNA-KMPDEGCQSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.1673  -12.7066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6872  -13.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100  -13.1152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100  -12.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035  -11.7543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2473  -10.7012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8538  -11.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6872  -12.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2467  -13.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2467  -14.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100  -14.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4695  -14.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2189  -15.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893  -14.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4695  -13.3448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721  -14.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999  -14.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6352  -10.9944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8622  -10.4057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1  9  1  0
  4  9  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  1
 17 18  1  0
 10 16  1  0
 10  3  1  6
  8 19  1  0
  6 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3248868

   (2S,3S,4S,5R)-2-(6-amino-2-methoxypurin-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: 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. Montgomery JA, Shortnacy AT, Arnett G, Shannon WM..  (1977)  2-Substituted derivatives of 9-alpha-D-arabinofuranosyladenine and 9-alpha-D-arabinofuranosyl-8-azaadenine.,  20  (3): [PMID:191611] [10.1021/jm00213a017]

Source

Source(1):

• Scientific Literature