(1S,2S,4S,5S)-4-(6-amino-9H-purin-9-yl)-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol

ID: ALA5270911

Max Phase: Preclinical

Molecular Formula: C12H15N5O2

Molecular Weight: 261.29

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@]2(CO)C[C@H]12

Standard InChI:  InChI=1S/C12H15N5O2/c13-10-9-11(15-4-14-10)17(5-16-9)7-1-8(19)12(3-18)2-6(7)12/h4-8,18-19H,1-3H2,(H2,13,14,15)/t6-,7+,8+,12-/m1/s1

Standard InChI Key:  GJDYOCPKYJVOMS-MOEZTCPLSA-N

Molfile:  

 
     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
    0.1267   -2.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867   -1.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -1.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2641   -1.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -0.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566   -0.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3626   -1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570    0.3053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4282    0.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570    1.6414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8423    1.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8423    0.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5564    0.1537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2641    0.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2641    1.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545    1.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545    2.6222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124   -1.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.2684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  1
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  2  1  0
  7  9  1  1
  9 10  1  0
 10 11  2  0
 12 11  1  0
 12 13  1  0
 13  9  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 17 18  1  0
  6 19  1  0
  3 19  1  0
  6 20  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5270911

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 261.29

Molecular Weight (Monoisotopic): 261.1226

AlogP: -0.29

#Rotatable Bonds: 2

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: 3.76

CX LogP: -1.49

CX LogD: -1.49

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.69

Np Likeness Score: 1.28

References

1. Jacobson KA, Salmaso V, Suresh RR, Tosh DK..  (2021)  Expanding the repertoire of methanocarba nucleosides from purinergic signaling to diverse targets.,  12  (11.0): [PMID:34825182] [10.1039/D1MD00167A]

Source

Source(1):

• Scientific Literature