{(1R*,3R*,4R*)-3-[6-(Cyclopropylamino)-9H-purin-9-yl]bicyclo[2.2.1]hept-1-yl}methanol

ID: ALA3353010

PubChem CID: 118719390

Max Phase: Preclinical

Molecular Formula: C16H21N5O

Molecular Weight: 299.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@]12CC[C@H](C1)[C@H](n1cnc3c(NC4CC4)ncnc31)C2

Standard InChI:  InChI=1S/C16H21N5O/c22-7-16-4-3-10(5-16)12(6-16)21-9-19-13-14(20-11-1-2-11)17-8-18-15(13)21/h8-12,22H,1-7H2,(H,17,18,20)/t10-,12-,16-/m1/s1

Standard InChI Key:  ZWYRKODAWPMOAL-NSODJVPESA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
   27.9122   -3.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6218   -2.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6190   -2.0063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9104   -1.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2041   -2.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2053   -2.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4292   -1.7594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9482   -2.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4272   -3.0806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9066   -0.7839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1735   -3.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3983   -4.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3971   -4.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1740   -5.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6552   -4.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7353   -5.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9893   -5.0692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9726   -5.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2315   -5.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4419   -4.3006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.6124   -0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4269   -0.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0150    0.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  4 10  1  0
 11  9  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 13 16  1  1
 16 17  1  0
 13 18  1  0
 15 19  1  0
 18 19  1  0
 15 20  1  1
 10 21  1  0
 22 21  1  0
 23 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3353010

   ---

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: 299.38

Molecular Weight (Monoisotopic): 299.1746

AlogP: 2.12

#Rotatable Bonds: 4

Polar Surface Area: 75.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.55

CX LogP: 1.02

CX LogD: 1.02

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.90

Np Likeness Score: 0.10

References

1. Dejmek M, Šála M, Hřebabecký H, Dračínský M, Procházková E, Chalupská D, Klíma M, Plačková P, Hájek M, Andrei G, Naesens L, Leyssen P, Neyts J, Balzarini J, Boura E, Nencka R..  (2015)  Norbornane-based nucleoside and nucleotide analogues locked in North conformation.,  23  (1): [PMID:25435471] [10.1016/j.bmc.2014.11.011]

Source

Source(1):

• Scientific Literature