(Z)-1-(4-Amino-2-butenyl)-5-methylcytosine

ID: ALA2261784

PubChem CID: 53232469

Max Phase: Preclinical

Molecular Formula: C9H14N4O

Molecular Weight: 194.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn(C/C=C\CN)c(=O)nc1N

Standard InChI:  InChI=1S/C9H14N4O/c1-7-6-13(5-3-2-4-10)9(14)12-8(7)11/h2-3,6H,4-5,10H2,1H3,(H2,11,12,14)/b3-2-

Standard InChI Key:  BUHCOYARYJTIJC-IHWYPQMZSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
   11.0886  -20.5223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0886  -21.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8031  -21.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3742  -21.7598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6597  -21.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9452  -21.7598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6597  -20.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3742  -20.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9452  -20.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8031  -20.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5176  -20.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2321  -20.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2321  -19.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9465  -18.8723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  1  8  1  0
  7  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
  1 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2261784

   (Z)-1-(4-Amino-2-butenyl)-5-methylcytosine

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: 194.24

Molecular Weight (Monoisotopic): 194.1168

AlogP: -0.35

#Rotatable Bonds: 3

Polar Surface Area: 86.93

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.65

CX LogP: -0.89

CX LogD: -3.08

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.64

Np Likeness Score: -0.43

References

1. Wittine K, Benci K, Kraljevic Pavelic S, Pavelic K, Bratulic S, Hock K, Balzarini J, Mintas M.  (2011)  Synthesis, cytostatic and anti-viral activity evaluation of the novel acyclic nucleoside analogues containing a sterically constrained (Z)-4-amino-2-butenyl moiety,  20  (3): [10.1007/s00044-010-9318-1]

Source

Source(1):

• Scientific Literature