((1R,2R,3S,4R)-4-(2-(benzylamino)pyrimidin-4-ylamino)-2,3-dihydroxycyclopentyl)methyl sulfamate

ID: ALA3984873

PubChem CID: 59671310

Max Phase: Preclinical

Molecular Formula: C17H23N5O5S

Molecular Weight: 409.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@H]1C[C@@H](Nc2ccnc(NCc3ccccc3)n2)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H23N5O5S/c18-28(25,26)27-10-12-8-13(16(24)15(12)23)21-14-6-7-19-17(22-14)20-9-11-4-2-1-3-5-11/h1-7,12-13,15-16,23-24H,8-10H2,(H2,18,25,26)(H2,19,20,21,22)/t12-,13-,15-,16+/m1/s1

Standard InChI Key:  WSVVYAYWXLZXJS-XOUADPBQSA-N

Molfile:  

     RDKit          2D

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    1.5972   -5.6956    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057   -4.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -6.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411   -6.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0944   -5.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4325   -5.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7687   -5.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5383   -7.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3200   -7.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913   -5.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811   -5.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -6.2456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8763   -5.4002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0471   -4.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8229   -4.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3909   -3.0068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6119   -3.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4369   -4.0577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0071   -2.7072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1806   -1.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9590   -1.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5602   -2.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3357   -1.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5135   -1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9093   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1274   -0.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  5  1  0
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  7  8  1  0
  8  4  1  0
  4  9  1  6
  5 10  1  6
  8 11  1  1
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  2 13  1  0
  6 14  1  1
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 26 27  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3984873

   [(1R,2R,3S,4R)-4-[[2-(benzylamino)pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]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: 409.47

Molecular Weight (Monoisotopic): 409.1420

AlogP: -0.17

#Rotatable Bonds: 8

Polar Surface Area: 159.69

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.39

CX Basic pKa: 7.14

CX LogP: -0.35

CX LogD: -0.53

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -0.22

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