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

ID: ALA467047

PubChem CID: 44574108

Max Phase: Preclinical

Molecular Formula: C16H25N7O3

Molecular Weight: 363.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(N)c2ncn([C@@H]3O[C@H](CN(C)C/C=C\CN)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C16H25N7O3/c1-9-20-14(18)11-15(21-9)23(8-19-11)16-13(25)12(24)10(26-16)7-22(2)6-4-3-5-17/h3-4,8,10,12-13,16,24-25H,5-7,17H2,1-2H3,(H2,18,20,21)/b4-3-/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  MTDBNJKMVASAKC-LNNUBQDUSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.7338   -5.7291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7324   -6.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4455   -6.9696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4435   -5.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1617   -5.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1622   -6.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9532   -6.8131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4416   -6.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9523   -5.4676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2064   -7.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7220   -8.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2073   -8.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9918   -8.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9912   -7.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4396   -4.4913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6583   -7.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6596   -9.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9529   -9.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1460   -9.8897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8915  -10.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5936   -9.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8481   -8.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2956   -7.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4888   -8.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2344   -8.8363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0174   -6.9681    0.0000 C   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:

   

   ALA467047

   (2R,3R,4S,5R)-2-(6-amino-2-methyl-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: 363.42

Molecular Weight (Monoisotopic): 363.2019

AlogP: -1.22

#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: -1.17

CX LogD: -3.81

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: 0.32

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