((1S,2S,4R)-4-(6-(4-chlorobenzyloxy)pyrimidin-4-yloxy)-2-hydroxycyclopentyl)methyl sulfamate

ID: ALA3986740

PubChem CID: 59671221

Max Phase: Preclinical

Molecular Formula: C17H20ClN3O6S

Molecular Weight: 429.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@@H]1C[C@@H](Oc2cc(OCc3ccc(Cl)cc3)ncn2)C[C@@H]1O

Standard InChI:  InChI=1S/C17H20ClN3O6S/c18-13-3-1-11(2-4-13)8-25-16-7-17(21-10-20-16)27-14-5-12(15(22)6-14)9-26-28(19,23)24/h1-4,7,10,12,14-15,22H,5-6,8-9H2,(H2,19,23,24)/t12-,14+,15-/m0/s1

Standard InChI Key:  WMINRTBWDIVBGQ-CFVMTHIKSA-N

Molfile:  

     RDKit          2D

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   18.7091  -13.5804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1421  -14.2802    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.5317  -13.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5565  -15.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3737  -15.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6280  -14.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9651  -13.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3063  -14.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0753  -15.6754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5290  -13.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4056  -13.9867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9220  -14.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5376  -14.8280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5766  -13.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3555  -12.9406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5267  -12.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9198  -11.5938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1391  -11.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9716  -12.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5306  -11.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6988  -10.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4754  -10.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0817  -10.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8578  -10.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0266   -9.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4132   -9.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6396   -9.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8029   -9.4873    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
  6 11  1  1
 10 12  1  0
 12  2  1  0
  2 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986740

   [(1S,2S,4R)-4-[6-[(4-chlorophenyl)methoxy]pyrimidin-4-yl]oxy-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: 429.88

Molecular Weight (Monoisotopic): 429.0761

AlogP: 1.45

#Rotatable Bonds: 8

Polar Surface Area: 133.86

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.40

CX Basic pKa: 3.42

CX LogP: 1.60

CX LogD: 1.60

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -0.30

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