(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-((((Z)-4-aminobut-2-enyl)(methyl)amino)methyl)-4-fluorotetrahydrofuran-3-ol

ID: ALA466624

PubChem CID: 25141776

Max Phase: Preclinical

Molecular Formula: C15H22FN7O2

Molecular Weight: 351.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C/C=C\CN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](F)[C@@H]1O

Standard InChI:  InChI=1S/C15H22FN7O2/c1-22(5-3-2-4-17)6-9-12(24)10(16)15(25-9)23-8-21-11-13(18)19-7-20-14(11)23/h2-3,7-10,12,15,24H,4-6,17H2,1H3,(H2,18,19,20)/b3-2-/t9-,10-,12-,15-/m1/s1

Standard InChI Key:  NPGZZLCILZSYOC-KJUCIFOFSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.2542    2.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530    1.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659    1.1795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639    2.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821    2.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    1.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4737    1.3359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    2.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4729    2.6814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270    0.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2424   -0.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7277   -0.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5122   -0.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117    0.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9601    3.6578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800   -1.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -1.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.7406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4120   -2.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -1.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3685   -0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162    0.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0092    0.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548   -0.6872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1787    0.7819    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 10  7  1  1
  1  2  2  0
  4 15  1  0
  5  4  2  0
 13 16  1  6
  6  7  1  0
 12 17  1  1
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 18 20  1  0
 10 11  1  0
 20 21  1  0
  4  1  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
 23 24  1  0
  2  3  1  0
 14 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA466624

   (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(((4-aminobut-2-enyl)(methyl)amino)methyl)-4-fluorotetrahydrofuran-3-ol

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: 351.39

Molecular Weight (Monoisotopic): 351.1819

AlogP: -0.55

#Rotatable Bonds: 6

Polar Surface Area: 128.34

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.75

CX Basic pKa: 9.65

CX LogP: -0.76

CX LogD: -3.59

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 0.31

References

1. Hirth B, Barker RH, Celatka CA, Klinger JD, Liu H, Nare B, Nijjar A, Phillips MA, Sybertz E, Willert EK, Xiang Y..  (2009)  Discovery of new S-adenosylmethionine decarboxylase inhibitors for the treatment of Human African Trypanosomiasis (HAT).,  19  (11): [PMID:19419862] [10.1016/j.bmcl.2009.04.096]

2. Barker RH, Liu H, Hirth B, Celatka CA, Fitzpatrick R, Xiang Y, Willert EK, Phillips MA, Kaiser M, Bacchi CJ, Rodriguez A, Yarlett N, Klinger JD, Sybertz E..  (2009)  Novel S-adenosylmethionine decarboxylase inhibitors for the treatment of human African trypanosomiasis.,  53  (5): [PMID:19289530] [10.1128/aac.01674-08]

Source

Source(1):

• Scientific Literature