((1S,2S,4R)-4-(8-(3-chlorophenyl)-9H-purin-6-ylamino)-2-hydroxycyclopentyl)methyl sulfamate

ID: ALA3984306

PubChem CID: 59671410

Max Phase: Preclinical

Molecular Formula: C17H19ClN6O4S

Molecular Weight: 438.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@@H]1C[C@@H](Nc2ncnc3[nH]c(-c4cccc(Cl)c4)nc23)C[C@@H]1O

Standard InChI:  InChI=1S/C17H19ClN6O4S/c18-11-3-1-2-9(4-11)15-23-14-16(20-8-21-17(14)24-15)22-12-5-10(13(25)6-12)7-28-29(19,26)27/h1-4,8,10,12-13,25H,5-7H2,(H2,19,26,27)(H2,20,21,22,23,24)/t10-,12+,13-/m0/s1

Standard InChI Key:  POUVZNNLXKKNSI-UHTWSYAYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   31.4990  -16.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9117  -17.3591    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.3201  -16.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3261  -18.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1433  -18.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3977  -17.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7347  -16.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0760  -17.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8449  -18.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2987  -17.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6916  -17.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3073  -17.9069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1752  -17.0656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3462  -16.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1251  -16.0195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2963  -15.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6895  -14.6727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7412  -15.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9042  -14.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1970  -14.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5968  -15.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9333  -15.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8003  -14.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5427  -14.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7429  -13.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1999  -14.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4622  -15.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2613  -15.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4848  -13.1965    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  4  9  1  6
  8 10  1  6
 10 11  1  0
 11  2  1  0
  2 12  1  0
  6 13  1  1
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 19  1  0
 18 14  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 21 23  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3984306

   [(1S,2S,4R)-4-[[8-(3-chlorophenyl)-7H-purin-6-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate

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: 438.90

Molecular Weight (Monoisotopic): 438.0877

AlogP: 1.44

#Rotatable Bonds: 6

Polar Surface Area: 156.11

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.23

CX Basic pKa: 3.85

CX LogP: 0.74

CX LogD: 0.74

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -0.58

References

1.  (2008)  Heteroaryl compounds useful as inhibitors of E1 activating enzymes, 

2.  (2013)  Inhibitors of nedd8-activating enzyme, 

Source

Source(1):

• Patent Bioactivity Data