6-deoxycyclopropavir

ID: ALA2013103

PubChem CID: 57520880

Max Phase: Preclinical

Molecular Formula: C11H13N5O2

Molecular Weight: 247.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6-Deoxycyclopropavir | 6-Deoxycyclopropavir|CHEMBL2013103|[(2Z)-2-[(2-aminopurin-9-yl)methylene]-1-(hydroxymethyl)cyclopropyl]methanol

Canonical SMILES:  Nc1ncc2ncn(/C=C3/CC3(CO)CO)c2n1

Standard InChI:  InChI=1S/C11H13N5O2/c12-10-13-2-8-9(15-10)16(6-14-8)3-7-1-11(7,4-17)5-18/h2-3,6,17-18H,1,4-5H2,(H2,12,13,15)/b7-3-

Standard InChI Key:  YJSKWTGXALYVDY-CLTKARDFSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    0.6866    0.6925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024    1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3995    1.9352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848    2.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263    1.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8136    2.1903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    1.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156    0.8503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1169    0.6945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714    0.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8779   -0.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929   -0.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    0.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885    0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8962    0.8703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3848    1.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9  5  1  0
  4  6  1  0
  2 10  1  0
  5  6  2  0
  9 11  1  0
  1  2  2  0
 11 12  2  0
 13 12  1  0
 14 13  1  0
 12 14  1  0
  5  1  1  0
  2  3  1  0
 13 15  1  0
  3  4  2  0
 13 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  2  0
 15 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2013103

   [(2Z)-2-[(2-aminopurin-9-yl)methylene]-1-(hydroxymethyl)cyclopropyl]methanol

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: 247.26

Molecular Weight (Monoisotopic): 247.1069

AlogP: -0.38

#Rotatable Bonds: 3

Polar Surface Area: 110.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.35

CX LogP: -1.53

CX LogD: -1.53

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.68

Np Likeness Score: 0.06

References

1. Li C, Quenelle DC, Prichard MN, Drach JC, Zemlicka J..  (2012)  Synthesis and antiviral activity of 6-deoxycyclopropavir, a new prodrug of cyclopropavir.,  20  (8): [PMID:22417649] [10.1016/j.bmc.2012.02.031]

Source

Source(1):

• Scientific Literature