[5-(2-Amino-6-oxo-1,6-dihydro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid ammonium salt

ID: ALA1160823

PubChem CID: 136016328

Max Phase: Preclinical

Molecular Formula: C10H17N6O5P

Molecular Weight: 315.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N.Nc1nc(O)c2ncn(C[C@@H]3CC[C@@H](P(=O)(O)O)O3)c2n1

Standard InChI:  InChI=1S/C10H14N5O5P.H3N/c11-10-13-8-7(9(16)14-10)12-4-15(8)3-5-1-2-6(20-5)21(17,18)19;/h4-6H,1-3H2,(H2,17,18,19)(H3,11,13,14,16);1H3/t5-,6+;/m0./s1

Standard InChI Key:  WOYLOTLIDLHXLF-RIHPBJNCSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    1.7167    0.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -2.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -2.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792   -1.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -1.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -3.0542    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -2.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -2.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -0.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -2.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667   -3.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -2.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  2  0
  5  2  1  0
  6  9  2  0
  7  3  1  0
  8  3  2  0
  9  4  1  0
 12 10  1  1
 11  5  1  0
 12 13  1  0
 13 17  1  0
 14  5  1  0
 15 10  2  0
 16  8  1  0
 17 14  1  6
 18 22  1  0
 19  9  1  0
 20 10  1  0
 21 10  1  0
 22 17  1  0
  7 11  2  0
  8  6  1  0
 12 18  1  0
M  END

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: 315.23

Molecular Weight (Monoisotopic): 315.0733

AlogP: -0.20

#Rotatable Bonds: 3

Polar Surface Area: 156.61

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.30

CX Basic pKa: 0.73

CX LogP: -1.24

CX LogD: -3.27

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.56

Np Likeness Score: -0.17

References

1. Bubenik M, Rej R, Nguyen-Ba N, Attardo G, Ouellet F, Chan L..  (2002)  Novel nucleotide phosphonate analogues with potent antitumor activity.,  12  (21): [PMID:12372502] [10.1016/s0960-894x(02)00679-0]

Source

Source(1):

• Scientific Literature