Acetic acid 4-acetoxy-2-{[(4-amino-but-2-enyl)-methyl-amino]-methyl}-5-(6-amino-purin-9-yl)-tetrahydro-furan-3-yl ester

ID: ALA359376

PubChem CID: 44365398

Max Phase: Preclinical

Molecular Formula: C19H27N7O5

Molecular Weight: 433.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC1C(CN(C)C/C=C\CN)OC(n2cnc3c(N)ncnc32)C1OC(C)=O

Standard InChI:  InChI=1S/C19H27N7O5/c1-11(27)29-15-13(8-25(3)7-5-4-6-20)31-19(16(15)30-12(2)28)26-10-24-14-17(21)22-9-23-18(14)26/h4-5,9-10,13,15-16,19H,6-8,20H2,1-3H3,(H2,21,22,23)/b5-4-

Standard InChI Key:  ZIZMOTPTRQWNLN-PLNGDYQASA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    8.2667   -2.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -1.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5542   -3.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -2.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -5.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -1.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -5.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -6.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -7.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -7.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -4.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -0.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3917   -5.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -5.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  9  2  0
  7  2  1  0
  8  3  1  0
  9  1  1  0
 10  7  1  0
 11  5  1  0
 12  4  1  0
 13  3  1  0
 14 16  1  0
 15  8  1  0
 16 12  2  0
 17 13  1  0
 18 10  1  0
 19 15  1  0
 20 17  2  0
 21 19  2  0
 22 27  1  0
 23 22  2  0
 24 18  1  0
 25 11  1  0
 26 28  1  0
 27 24  1  0
 28 23  1  0
 29 19  1  0
 30 17  1  0
 31 24  1  0
  5  6  1  0
 10  8  1  0
 11 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA359376

   [4-acetyloxy-2-[[[(Z)-4-aminobut-2-enyl]-methylamino]methyl]-5-(6-aminopurin-9-yl)oxolan-3-yl] acetate

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: 433.47

Molecular Weight (Monoisotopic): 433.2074

AlogP: -0.38

#Rotatable Bonds: 8

Polar Surface Area: 160.71

Molecular Species: BASE

HBA: 12

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.65

CX LogP: -0.77

CX LogD: -3.85

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: 0.63

References

1. Marasco CJ, Kramer DL, Miller J, Porter CW, Bacchi CJ, Rattendi D, Kucera L, Iyer N, Bernacki R, Pera P, Sufrin JR..  (2002)  Synthesis and evaluation of analogues of 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine as inhibitors of tumor cell growth, trypanosomal growth, and HIV-1 infectivity.,  45  (23): [PMID:12408722] [10.1021/jm0201621]

Source

Source(1):

• Scientific Literature