9-alpha-D-ArabinofuranosyI-2-hydrazinoadenine

ID: ALA3248870

PubChem CID: 53672648

Max Phase: Preclinical

Molecular Formula: C10H15N7O4

Molecular Weight: 297.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NNc1nc(N)c2ncn([C@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)c2n1

Standard InChI:  InChI=1S/C10H15N7O4/c11-7-4-8(15-10(14-7)16-12)17(2-13-4)9-6(20)5(19)3(1-18)21-9/h2-3,5-6,9,18-20H,1,12H2,(H3,11,14,15,16)/t3-,5-,6+,9+/m1/s1

Standard InChI Key:  BAYFDGKAUSOEIS-ICKFSKTQSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.9432  -21.4605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4631  -22.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6859  -21.8690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6859  -21.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794  -20.5081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2460  -19.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233  -19.4551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6297  -20.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4631  -20.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0226  -22.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0226  -23.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6859  -23.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454  -23.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9948  -24.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652  -22.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454  -22.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480  -22.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5758  -23.4854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4111  -19.7482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6381  -19.1595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070  -18.3600    0.0000 N   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:

   

   ALA3248870

   (2S,3S,4S,5R)-2-(6-amino-2-hydrazinylpurin-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: 297.28

Molecular Weight (Monoisotopic): 297.1186

AlogP: -2.69

#Rotatable Bonds: 3

Polar Surface Area: 177.59

Molecular Species: BASE

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.45

CX Basic pKa: 10.86

CX LogP: -2.02

CX LogD: -3.86

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.26

Np Likeness Score: 0.73

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