(2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-((((Z)-4-aminobut-2-enyl)(methyl)amino)methyl)tetrahydrofuran-3,4-diol

ID: ALA468092

PubChem CID: 25141896

Max Phase: Preclinical

Molecular Formula: C15H22ClN7O3

Molecular Weight: 383.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C/C=C\CN)C[C@H]1O[C@@H](n2cnc3c(N)nc(Cl)nc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H22ClN7O3/c1-22(5-3-2-4-17)6-8-10(24)11(25)14(26-8)23-7-19-9-12(18)20-15(16)21-13(9)23/h2-3,7-8,10-11,14,24-25H,4-6,17H2,1H3,(H2,18,20,21)/b3-2-/t8-,10-,11-,14-/m1/s1

Standard InChI Key:  DVPZNDPOWUEVAP-UKSTWOGXSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.6603    2.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6591    1.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3720    0.7899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3700    2.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0882    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0888    1.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8799    0.9463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3683    1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8790    2.2918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1331    0.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6485   -0.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1339   -1.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9184   -0.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9178   -0.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3662    3.2682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5848    0.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5862   -1.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8794   -1.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0726   -2.1302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8182   -2.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5202   -1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7746   -0.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2223   -0.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4153   -0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1609   -1.0768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9440    0.7913    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  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
 14 16  1  6
  6  7  1  0
 13 17  1  6
  7  8  1  0
 12 18  1  1
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  1  0
 10 11  1  0
 19 21  1  0
  4  1  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 24  1  0
  2  3  1  0
 24 25  1  0
  3  6  2  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA468092

   (2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-((((Z)-4-aminobut-2-enyl)(methyl)amino)methyl)tetrahydrofuran-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: 383.84

Molecular Weight (Monoisotopic): 383.1473

AlogP: -0.87

#Rotatable Bonds: 6

Polar Surface Area: 148.57

Molecular Species: BASE

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.47

CX Basic pKa: 9.65

CX LogP: -0.74

CX LogD: -3.36

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.37

Np Likeness Score: 0.43

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