((1S,2S,4R)-2-hydroxy-4-(8-o-tolyl-9H-purin-6-ylamino)cyclopentyl)methyl sulfamate

ID: ALA3982239

PubChem CID: 59671305

Max Phase: Preclinical

Molecular Formula: C18H22N6O4S

Molecular Weight: 418.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1-c1nc2c(N[C@@H]3C[C@@H](COS(N)(=O)=O)[C@@H](O)C3)ncnc2[nH]1

Standard InChI:  InChI=1S/C18H22N6O4S/c1-10-4-2-3-5-13(10)16-23-15-17(20-9-21-18(15)24-16)22-12-6-11(14(25)7-12)8-28-29(19,26)27/h2-5,9,11-12,14,25H,6-8H2,1H3,(H2,19,26,27)(H2,20,21,22,23,24)/t11-,12+,14-/m0/s1

Standard InChI Key:  ZHZRKVUPABKVMT-SCRDCRAPSA-N

Molfile:  

     RDKit          2D

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   31.3369  -14.4183    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.7492  -13.6990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7746  -15.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5996  -15.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8565  -14.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.5220  -14.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2888  -15.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7372  -14.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6416  -14.1219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1243  -14.6736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7265  -14.9714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8142  -13.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6007  -13.0657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7735  -12.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1608  -11.7059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2033  -12.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.6538  -11.5596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0479  -12.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3876  -12.8610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2436  -11.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9835  -11.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1761  -10.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6278  -11.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8926  -12.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6995  -12.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9626  -13.3458    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
  6 11  1  1
 10 12  1  0
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  2 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
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 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
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 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 21 23  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982239

   [(1S,2S,4R)-2-hydroxy-4-[[8-(2-methylphenyl)-7H-purin-6-yl]amino]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: 418.48

Molecular Weight (Monoisotopic): 418.1423

AlogP: 1.10

#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: 9.28

CX Basic pKa: 3.85

CX LogP: 0.65

CX LogD: 0.65

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -0.34

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