((1S,2S,4R)-2-hydroxy-4-(8-phenyl-9H-purin-6-yloxy)cyclopentyl)methyl sulfamate

ID: ALA3985244

PubChem CID: 59671216

Max Phase: Preclinical

Molecular Formula: C17H19N5O5S

Molecular Weight: 405.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@@H]1C[C@@H](Oc2ncnc3[nH]c(-c4ccccc4)nc23)C[C@@H]1O

Standard InChI:  InChI=1S/C17H19N5O5S/c18-28(24,25)26-8-11-6-12(7-13(11)23)27-17-14-16(19-9-20-17)22-15(21-14)10-4-2-1-3-5-10/h1-5,9,11-13,23H,6-8H2,(H2,18,24,25)(H,19,20,21,22)/t11-,12+,13-/m0/s1

Standard InChI Key:  NEMRBWQVVJBHKJ-XQQFMLRXSA-N

Molfile:  

     RDKit          2D

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   27.0994  -21.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5121  -22.4480    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.9205  -21.7356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9265  -23.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7437  -23.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9981  -22.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3351  -21.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6764  -22.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4453  -23.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8991  -22.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2920  -22.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9077  -22.9958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7756  -22.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3821  -22.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2088  -23.4994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8145  -24.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5931  -23.7955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1553  -22.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7632  -22.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4648  -22.5768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2906  -21.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4813  -21.7028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8302  -21.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6315  -21.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1740  -20.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9166  -19.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1115  -19.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5724  -20.4000    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA3985244

   [(1S,2S,4R)-2-hydroxy-4-[(8-phenyl-7H-purin-6-yl)oxy]cyclopentyl]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: 405.44

Molecular Weight (Monoisotopic): 405.1107

AlogP: 0.76

#Rotatable Bonds: 6

Polar Surface Area: 153.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.52

CX Basic pKa: 2.63

CX LogP: 0.51

CX LogD: 0.48

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -0.13

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