((1S,2S,4R)-4-{[8-(2,3-dimethoxyphenyl)-9H-purin-6-yl]amino}-2-hydroxycyclopentyl)methyl sulfamate

ID: ALA4581036

PubChem CID: 87157177

Max Phase: Preclinical

Molecular Formula: C19H24N6O6S

Molecular Weight: 464.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2nc3c(N[C@@H]4C[C@@H](COS(N)(=O)=O)[C@@H](O)C4)ncnc3[nH]2)c1OC

Standard InChI:  InChI=1S/C19H24N6O6S/c1-29-14-5-3-4-12(16(14)30-2)17-24-15-18(21-9-22-19(15)25-17)23-11-6-10(13(26)7-11)8-31-32(20,27)28/h3-5,9-11,13,26H,6-8H2,1-2H3,(H2,20,27,28)(H2,21,22,23,24,25)/t10-,11+,13-/m0/s1

Standard InChI Key:  IATMINVMLQNSTJ-LOWVWBTDSA-N

Molfile:  

 
     RDKit          2D

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   19.9853   -8.2755    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.1725   -8.1912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6942   -8.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8774   -8.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4664   -8.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6673   -8.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5830   -9.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3318   -9.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8012   -7.3144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8737   -9.4564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3908  -10.4358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9084  -11.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3918  -11.7589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1684  -11.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8784  -11.9114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5877  -11.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5869  -10.6859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8777  -10.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1684  -10.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0931  -11.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6821  -10.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8627  -10.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4534  -11.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8635  -11.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6837  -11.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4526   -9.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6332   -9.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0874   -9.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6773   -8.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3187   -9.0216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9799   -7.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7723   -8.0605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  4  8  1  0
  5  9  1  6
 11 12  2  0
 12 13  1  0
 13 14  1  0
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 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 11 19  1  0
 14 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
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 24 25  1  0
 20 25  2  0
 26 27  1  0
 22 26  1  0
 28 29  1  0
 21 28  1  0
 12 20  1  0
 10 18  1  0
  7 10  1  1
  4  3  1  6
  2  3  1  0
  1 30  1  0
  1 31  2  0
  1 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4581036

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

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 464.50

Molecular Weight (Monoisotopic): 464.1478

AlogP: 0.81

#Rotatable Bonds: 8

Polar Surface Area: 174.57

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.87

CX Basic pKa: 4.83

CX LogP: -0.17

CX LogD: -0.19

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: -0.16

References

1.  (2013)  Inhibitors of nedd8-activating enzyme, 

Source

Source(1):

• Patent Bioactivity Data